➢ Important Topics of this Chapter for Creative Question of (c) & (d):

Times
Board & Year the Questions Have
Questions
Importance Topic Appeared
Appeared
c d CQ
T-01: Isomerism and SB’23; BB’23, 19; MB’23; DB’22, 21, 19;
 6 8
nomenclature CB’22, 19; Ctg.B’19; All Board’18
DB’23, 22, 19; Ctg.B’23, 22; SB’23, 22, 19;
T-02: Alkane, Alkene and
 16 16 BB’23, 19; JB’23, 22, 21, 19; CB’23; Din.B’23,
Alkyne
22, 21, MB’23; RB’22, 19
T-03: Alkyl halide and 𝐒𝐍 𝟏, Ctg.B’23, 22, 19; JB’23; CB’23, 21; RB’22,
 7 5
𝐒𝐍 𝟐, 𝐄𝟏 , 𝐄𝟐 21; Din.B’22; MB’22; DB’21; All Board’18
RB’23, 22; Ctg.B’23, 22; SB’23, 21; Din.B’23,
 T-04: Alcohol and Ether 14 4 21; JB’22; DB’21; CB’21; MB’21; BB’19;
All Board’18
DB’23, 22, 21, 19; RB’23, 21, 19; SB’23, 22,
19; BB’23, 22, 21; CB’23, 22, 21, 19; Din.B’23,
 T-05: Aldehyde and Ketone 11 27
22, 19; MB’23, 22, 21; Ctg.B’22, 19; JB’22, 19;
All Board’18
T-06: Carboxylic acid, acid
 halide, Amide, Amine, 5 0 JB’22; SB’21; Din.B’19; DB’17; RB’17
Anhydride and Ester
DB’23, 22, 21; RB’23, 22, 21, 19; Ctg.B’23, 22,
 T-07: Aromatic compound 27 30 21, 19; BB’23, 22, 21; JB’23, 21, 19; CB’23,
21; Din.B’23, 22, 21, 19; MB’23, 22, 21; SB’21

T-01: Isomerism and nomenclature

𝟐% 𝐇𝐠 𝟐+ 𝐑𝐞𝐚𝐫𝐫𝐚𝐧𝐠𝐞𝐦𝐞𝐧𝐭
01. 𝐂𝐇𝟑 − 𝐂 ≡ 𝐂𝐇 + 𝐇𝟐 𝐎 → 𝐓→ 𝐗 [SB’23]
𝟐𝟎% 𝐇𝟐 𝐒𝐎𝟒
∆
(𝐇𝐂𝐎𝐎)𝟐 𝐂𝐚 → 𝐘 + 𝐂𝐚𝐂𝐎𝟑
(c) X-compound shows tautomerism. Explain. 3
Answer
(c) Completing the first reaction of the stem we get:

1
 Tautomerism is the spontaneous transformation of isomers from a structure with one kind of functional group
to another.
C3 H6 O has two isomers CH3 COCH3 and CH3 C(OH) = CH2 which show tautomerism and remains in
dynamic equilibrium. That means:

02. [BB’23]
𝐇𝟐
𝐂𝐧 𝐇𝟐𝐧−𝟐 →
(𝐗) 𝐏𝐝+𝐁𝐚𝐒𝐎𝟒

Here, 𝐧 = 𝟒
(d) Which one between X and Z is able show geometric isomerism? Analyze the reasons. 4
Answer
(d) We get from c,
X is CH3 − CH2 − C ≡ CH and Z is CH3 − CH = CH − CH3
That is, compound Z can exhibit geometric isomerism between compounds X and Z.
Compounds in which free rotation along the axis of the carbon-carbon double bond is not possible result in
two types of compound molecules with different configurations; they are geometric isomers and properties
of such compounds are called geometric isomerism or cis-trans isomerism.
Two conditions of geometrical isomerism:
(1) Generally, substituted alkene with formula abC = Cab or abC = Cad can show geometrical isomerism.
(2) Cyclic organic compounds show geometrical isomerism.
(CH3 − CH = CH − CH3 )
Here, compound Z will show geometrical isomerism.

cis- but-2-ene trans − but-2-ene

But due to presence of carbon carbon triple bond in X, it cannot fill up the conditions of geometric isomerism.
So, though Z shows geometrical isomerism, X doesn’t.
03. [MB’23]

(d) Analyze which of the compound between M and N shows stereo isomerism. 4
Answer
(d) C4 H9 Br + KOH(alc) → CH3 − CH = CH − CH3 (80%) + CH3 − CH2 − CH = CH2 (20%)
(M) Butene−2 (N) Butene−1
The compounds from which two compound molecule with different configuration are formed as free rotation
along the carbon-carbon double bond axis is not possible, are called geometric isomers and the nature of
such compounds is called geometric isomerism or cis-trans isomerism.

2
 Two conditions of geometric isomerism:
(1) usually substituted alkene with formula abC = Cab or abC = Cad shows geometrical isomerism.
(2) Cyclic organic compounds show geometrical isomerism.
(CH3 − CH = CH − CH3 )
M
Here, M compound will show geometric isomerism.

cis- Butene trans − Butene

Here, M compound shows cis-trans isomerism. On the other hand, N compound is (CH3 − CH2 − CH = CH2 ).

Here, as there are two hydrogens being attached with the 1 no. carbon i.e., condition 1 not being obeyed, the
compound doesn’t show cis-trans isomerism.
04. [DB’22]

(d) Analyze which of the compounds M and N shows geometric isomerism. 4

Answer
(d) The compounds M and N show geometric isomerism similar to the (d) of board question no. 03, T-01.
05. Read the following and answer the given questions: [CB’22]

(c) Which one shows geometric isomerism among the compounds above? Explain. 3
(d) Compound (iii) in stem shows completely different isomerism from other two compounds in stem
– justify. 4
Answer
(c) According to the condition of geometric isomerism, Usually, substituted alkene with formula abC = Cab or
abC = Cad shows geometric isomerism.
For compound (i), if (−CH3 ) indicates a, (−Cl) indicates b and (−H) indicates d then the compound fulfill
the condition of geometric isomerism. So, it shows geometric isomerism.

3
 Compound (i) is:

Geometric isomer of each other

(d) (i) Number compound of stem shows geometric isomerism and (ii) shows positional isomerism. But (iii)
shows optically active isomerism.
According to the condition of optical isomerism,
➢ Chiral carbon should be present.
➢ Both isomers should be mirror image of each other.
➢ Both configurations are mirror images of each other. By all these conditions compound (iii) shows
optically active isomerism.
Optically active isomers are:

l-isomer d-isomer
By showing optically active isomerism, compound (iii) is completely different from other two compounds
in respect of isomerism.

06. [DB’21]

P doesn’t react with Tollen’s reagent but Q does.

(c) In stem which stereo isomerism is shown by B compound? Explain. 3
Answer
(c) Similar to the (d) of board question no: 03, T-01. Here, B = But-2-ene, CH3 − CH = CH − CH3

07. [DB’19]
(𝐢)𝐎𝟑 𝐊𝐎𝐇 (𝐚𝐥𝐜) 𝐊𝐎𝐇 (𝐚𝐪) 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕
𝟐 ‘𝐁’ ← ‘𝐀’ ← ‘𝐗’ → ‘Y’ → ‘Z’
(𝐢𝐢)𝐙𝐧/𝐇𝟐 𝐎 +𝐇𝟐 𝐒𝐎𝟒

′𝐗 ′ = An isomer of 𝐂𝟒 𝐇𝟗 Br; ′Z′ or ′𝐁′ + 𝟐, 4-DNPH→ Yellow Precipitate

′𝐁′ + Tollen’s reagent →Ag mirror
(c) Determine the structural formula of the compound ′𝐗′ according to the stem. 3

4
 Answer
(c) Since, from stem A reacts with O3 so, A is an alkene. The reaction of X with KOH(alc. ) is an elimination
reaction, that means X is an alkyl halide. It the stem, since A reacts with O3 , A is an alkene. the carbon
number of X is 4 so, X must be a 4 carbon alkene. Butene-2 is the 4 carbon symmetric Alkene which can be
obtained from alkyl halide. So, X is a 2° alkyl halide.
Therefore, CH3 − CH − CH2 − CH3
|
Br
2−bromobutane
Br
|
CH3 − CH − CH2 − CH3 + KOH(alc) → CH3 − CH = CH − CH3
‘X’ ‘A’
O Zn
CH3 − CH = CH − CH3 + O3 → CH3 − CH CH−CH3 + H2 O → 2CH3 CHO+ ZnO + H2 O
O O ‘B’
Br
|
Therefore, ′X′ is, CH3 − CH − CH2 − CH3

08. [Ctg.B’19]
isomer i. O3
A C+D
C4H8 ii. H2O/Zn
isomer i. O
B 3 2E
ii. H2O/Zn
[‘C’ does not create precipitate with Tollen’s reagent]
(c) Explain stereo isomerism of compound ‘B’. 3
Answer
(c) Similar to the (d) of board question no. 03, T-01 B: CH3 − CH = CH − CH3
09. [BB’19]
Following is an organic reaction:
𝐂𝐇𝟑 𝐂𝐇𝟑
| |
𝐂𝟐 𝐇𝟓 − 𝐂 = 𝐂𝐇𝐂𝐥 + 𝐇𝐂𝐥 → 𝐂𝟐 𝐇𝟓 − 𝐂 − 𝐂𝐇𝟐 𝐂𝐥
(𝐀) |
𝐂𝐥
(𝐁)

(d) “Although 𝐀 & 𝐁 both show stereo isomerism, there is a difference of the said isomerism among
the two”-justify the statement. 4
Answer
(d) A & B show stereo isomerism. But A shows geometric isomerism and B shows optical isomerism.
A is a double bonded compound. Therefore, carbon-carbon free rotation is not possible in this case. Hence
it shows geometric isomerism. It will show E-Z isomerism since all valencies except double bond are
different species.
CH3 C 2 H5
\ /H \ /H
/ C= C\Cl / C = C\Cl
C 2 H5 CH3
Z isomer E isomer

5
 On the other hand, B has a chiral carbon. That is, all four valencies of carbon are filled up by different
species. For this reason, it is optically active.
C 2 H5 C 2 H5
| |
CH3 − C − Cl Cl − C − CH2
| |
CH2 Cl CH2 Cl
That is, both are enantiomers to each other. The equimolar mixture of these two are optically inactive and
also a racemic mixture.
A & B both are sterero isomers but A shows geometric isomerism while B shows optical isomerism.
D(80%) + HBr
10. (i) 2 C𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇(𝐁𝐫) − 𝐂𝐇𝟑 KOH (alc.) [CB.’19]
E(20%) + HBr
(d) Which one among D & E shows geometric isomerism? Explain with appropriate reason. 4
Answer
(d) Analysis of reason of showing geometric isomerism between D and E is similar to the (d) of board question
no. 02, T-01.

11. 𝐂𝐧 𝐇𝟐𝐧+𝟐 O; Here n = 4. [CB.’19]

(c) Write down the production of alkene by dehydration process from one of the isomers of the
compound in the stem. 3
(d) Which isomers of the compound in the stem can show metamerism? Explain. 4
Answer
(c) Description of preparing alkene by dehydrogenation method with reactions is similar to the (d) of board
question no: 07, T-03.

(d) In this case, alcohol and ether can be prepared from C4 H10 O. Ether shows metamerism. The type of
isomerism that arises due to difference in alkyl groups attached to the same functional group is called
metamerism. C4 H10 O has two ether metamers.
CH3 − O − CH2 CH2 CH3 CH3 CH2 − O − CH2 CH3
Methoxy propane (39°C boiling point) ethoxy ethane (34.5°C boiling point)
This is how metamerism is seen in ether.

12. [All B’18]

isomer i. O3
A ‘X’ + ‘Y’
ii. Zn/H 2O
C 4H8 isomer i. O3
B 2 ‘M’
ii. Zn/H 2O
['X' forms white precipitate with Tollen’s reagent but 'Y' doesn’t react with it]
(d) Analyze the possibility of exhibiting geometric isomerism for A and B. 4
Answer
(d) Analysis of possibility of exhibiting geometric isomerism for A and B is similar to the (d) of board
question no. 03, T-01.

6
 T-02: Alkane, Alkene and Alkyne

𝐇𝟐
01. 𝐂𝐚𝐂𝟐 + 𝐇𝟐 𝐎 → 𝐀→ 𝐁 [DB’23]
𝐏𝐝−𝐁𝐚𝐒𝐎𝟒
(d) Analyze which one between A and B is more acidic with equations. 4
Answer
(d) A is ethyne (CH ≡ CH) and B is ethene (CH2 = CH2 ). Alkyne-1 i.e., ethyne is more acidic than that of ethene.
A is more acidic between A and B. H-atom (−C ≡ C − H) attached with triple bond of alkyne-1 by covalent
bond shows slightly acidic nature. Because, due to the presence of sp3 , sp2 and sp hybridization in ethane,
ethene and ethyne respectively, s:p characteristic has been increased gradually. Such as: it has become 1:1,
1: 2 and 1:1. If there is more s-characteristics in a hybrid orbital, more overlapping occurs in formation of
sigma bond. So, nucleus of both C-atom is attracted more in carbon carbon bond of ethyne molecule. Then,
the carbon-carbon triple bond (C ≡ C) distance (0.120 nm) in alkyne becomes lower than that of carbon-
carbon double bond (C = C) distance (0.134 nm) in alkene. On the other hand, electron cloud in C-H sigma
bond, is more attracted toward the C-atom alkyne than that of alkene. That means, C-H bond of alkyne-1
becomes replaceable by metal as it becomes weak. So, ethyne (HC ≡ CH) and alkyne-1 becomes slight
acidic in nature. Then H atom of alkyne-1 is replaced by Na metal.
Liquid NH3
H − C ≡ C − H(g) + 2Na(s) → Na. C ≡ C. Na (s) + H2 (g)
Liquid NH3
CH2 = CH2 + 2Na → No reaction
𝐎𝟑 𝐙𝐧, ∆
02. 𝐀 (2-methyl-but-2-ene) → 𝐨𝐳𝐨𝐧𝐢𝐝𝐞 𝐜𝐨𝐦𝐩𝐨𝐮𝐧𝐝 → 𝐁 + 𝐂 +ZnO (Compound B doesn’t react
𝐂𝐂𝐥𝟒 𝐇𝟐 𝐎
with Tollen’s reagent). [Ctg.B’23]
(d) Will the nature of addition reaction of compound A and B be same? Analyze. 4
Answer
CH3
|
(d) Compound A of the stem is CH3 − C = CH − CH3 and compound B is CH3 COCH3
Both A and B of the stem gives addition reaction. But B gives nucleophilic addition reaction where A gives
electrophilic addition reaction.
Nucleophilic addition reaction:-
In aldehyde or ketone having bivalent carbonyl radical, nucleophilic addition reaction occurs. The pi (𝜋)
electron of carbonyl radical is attracted more towards the Oxygen atom as the difference of
electronegativity between carbon and oxygen is (3.5 − 2.5 = 1.0). As a result, partial negative (δ− ) charge

is formed in oxygen atom and partial positive δ+ ) charge is formed in carbon atom . In this way,
the negative nucleophilic reagent or the nucleophile easily attacks positive carbon atom of polarized
carbonyl radical and causes nucleophilic addition reaction. In this caser, cyanide ion (CN − ) (form HCN),
sodium sulphite ion ( −OSO2 Na) (from NaHSO3), molecule, grignard reagent and carbanion
act as nucleophile.
Electrophilic addition reaction: Its basically characteristics reaction of alkene and alkyne. In this case, if
pi electron of carbon-carbon double bond (C=C) reacts, then it acts as electron donator towards electrophile
or electrophilic reagents. Then the effect of electron in the solution from the reagents like: Cl2 , Br2 , HCl etc.
causes the reaction to occur.
7
03. [SB’23]

(d) Is it possible to produce compound Z from compound T? Analyze with reactions. 4

Answer
(d) Complete reaction of the stem:

Here, R = −CH3 ,
Na
2CH3 X + 2Na → CH3 − CH3 (T) + 2NaX
Dry ether
Dry ether H2 O
CH3 − X + Mg → CH3 − MgX → CH4 (Z) + MgX(OH)

Compound Z is possible to be produced from compound T.

Firstly, alkyl chloride is produced in reaction of alkane with Cl2 in presence of FeCl3 .
CH3 − CH3 (T) + Cl2 → CH3 − CH2 − Cl + HCl
CH3 − CH2 − Cl, NaOH(aq) produce alcohol-
CH3 CH2 − Cl + NaOH(aq) → CH3 − CH2 − OH + NaCl
Acid is produced from strong oxidation of alcohol:
[O] [O]
CH3 − CH2 − OH → CH3 CHO → CH3 COOH
K2 Cr2 O7 +H2 SO4 K2 Cr2 O7 +H2 SO4

Alkane is produced in the decarboxylation reaction (NaOH + CaO) of CH3 COOH .

CH3 COOH + NaOH → CH3 COONa + H2 O
NaOH
CH3 COONa → CH4 (Z) + Na2 CO3
CaO

𝐢. 𝐎𝐳𝐨𝐧𝐨𝐥𝐲𝐬𝐢𝐬
04. 2-methyl propene 𝐀 + 𝐁 + 𝐙𝐧𝐎 + 𝐇𝟐 𝐎 [BB’23]
𝐢𝐢. 𝐙𝐧/𝐇𝟐 𝐎
Compound A doesn’t give haloform reaction.
(c) Identify the compound A of the stem with essential reactions. 3
Answer
(c) Completing the reaction of the stem we get,
CH3 O
| i. Ozonolysis ∥
CH3 − C = CH2 → CH3 − C − CH3 + HCHO + ZnO + H2 O
2−Methyl propene ii. Zn/H2 O (B) (A)

A is HCHO which is the first member of aldehyde group. Carbonyl radical can be identified by 2,4-dinitro
phenyl hydrazine (2, 4 − DNPH) test. If few drops of (2, 4 − DNPH) is added to carbonyl compound, yellowish
-orange precipitation is formed.

↓ +H2 O

Carbonyl compound (2, 4 DNPH) 2:4 dinitrophenyl

hydrazone (yellow-orange)

8
05. [BB’23]
𝐇𝟐
𝐂𝐧 𝐇𝟐𝐧−𝟐 → B
(𝐗) 𝐏𝐝+𝐁𝐚𝐒𝐎𝟒

Here, 𝐧 = 𝟒 (Asymmetric)
(c) Explain the mechanism of reaction of Y with HBr in presence of 𝐇𝟐 𝐎𝟐 . 3
Answer
(c) Completing the reactions in the stem,

Therefore, Y is CH3 − CH2 − CH = CH2

Mechanism of reaction of HBr with CH3 − CH2 − CH = CH2 in presence of H2 O2 :

In the 1st step hydrogen peroxide dissociates

.
under heating to produce two (H − O) ) free-radicals. It then
attacks HBr to form the free-radical (Br). It attacks the butene in a second step to produce a more stable 2°
bromo alkyl free-radical. A 2° bromo alkyl free-radical reacts with a hydrogen atom (H) to form an excess
of 1 bromobutane according to the inverse Markovnikov rule.
In first step,
H − O O − H→ 2H − O
H − O + H Br → H − OH + Br [Bromine free radical]
In 2nd step,

Br + CH3 − CH2 − CH CH2 → CH3 − CH2 − CH − CHBr
More stable (2°)

Br + CH3 − CH2 − CH CH2 → CH3 − CH2 −CHBr − CH2
1° less stable
In 3rd step,

𝐡𝛎 𝐊𝐎𝐇(𝐚𝐪)
06. 𝐂𝐧 𝐇𝟐𝐧+𝟐 → 𝐂𝐧 𝐇𝟐𝐧+𝟏 𝐂𝐥 → 𝐑 [JB’23]
𝐏 𝐂𝐥𝟐
[𝐧=𝟏] 𝐐
(c) Explain the structure of compound P in the light of orbital hybridization. 3
Answer
(c) Compound P of the stem is methane (CH4 ).
Formation of 𝐬𝐩𝟑 hybridized carbon atom 𝐂𝐇𝟒 : Each sp3 hybrid orbital of the carbon atom has an
unpaired electron, which overlaps the 1s1 orbitals of the 4 H atoms to form 4 C − H sigma bonds to form
the methane molecule (CH4 ). Methane molecule has a bond angle of 109.5° and each covalent C − H bond
distance is 0.110 nm

9
 𝐇𝐁𝐫
07. 1. 2-Methyl butene-1 → 𝐀(𝟗𝟎%) + 𝐁(𝟏𝟎%) [CB’23]
(𝐦𝐚𝐣𝐨𝐫 𝐩𝐫𝐨𝐝𝐮𝐜𝐭) (𝐦𝐢𝐧𝐨𝐫 𝐩𝐫𝐨𝐝𝐮𝐜𝐭)
𝐍𝐚𝐎𝐇(𝐚𝐪)
2. A compound → 𝐂 compound
(d) Analyze the variation in percentage amount of product A and B by completing the reaction. 4
Answer

(d) Compound of the stem-2 methyl butene-1 (CH2 = C − C2 H5 )

|
CH3

According to Markovnikov's rule, in the reaction of an asymmetric reagent with an asymmetric alkyne, the
H or positive end of the alkene is attached to that double bonded carbon with more H atoms.
Here the reaction of 2-methylbutene-1 an asymmetrical alkene with the asymmetrical reagent HBr obeys
Markovnikov's law and the reaction is completed by HBr.

∴ percentage amount of product A and B is different due to the stability of carbocation and Markovnikov’s rule.

08. [CB’23]
𝐍𝐢⁄𝐏𝐭 (𝐢) 𝐎𝟑
𝐀 (𝐂𝐧 𝐇𝟐𝐧−𝟐 ) → 𝐁→ 𝐂+𝐃
(𝐧=𝟑) 𝐇𝟐 ,𝟐𝟎𝟎°𝐂 (𝐢𝐢)𝐙𝐧/𝐇𝟐𝐎
(𝐂 𝐚𝐧𝐝 𝐃 𝐚𝐫𝐞 𝟏 𝐚𝐧𝐝 𝟐 𝐜𝐚𝐫𝐛𝐨𝐧 𝐜𝐨𝐦𝐩𝐨𝐮𝐧𝐝 𝐫𝐞𝐬𝐩𝐞𝐜𝐭𝐢𝐯𝐞𝐥𝐲)

(c) Explain the acidic nature of compound A with equation. 3

Answer
(c) A of the stem is propyne. (CH ≡ C − CH3 )
Propyne or alkyne-1 compounds are acidic (mild). Basically, the carbon in propyne is sp hybridized, so that
the C-C length is relatively short i.e., 0.120 nm. Again, sp hybridized orbitals increase in electronegativity
as properties of s increases, so sp hybridization is more electronegative than sp2 or sp3 . Therefore, the C-H
bond shares the bond electron towards carbon, since the C-C bond length is relatively short. As a result, the
C-H bond becomes comparatively weaker. H can easily be replaced by being on the edge. As a result,
propyne acts as an acid by donating a proton (H + )
CH ≡ C − CH3 + [Ag(NH3 )2 ]NO3 → Ag C ≡ C − CH3 ↓ + NH4 NO3 + NH3
(white)

CH ≡ C − CH3 + [Cu(NH3 )2 ]Cl → CuC ≡ C − CH3 ↓ + NH4 Cl + NH3

(red)

From the reactions it can be seen, H at the terminal end of propyne is substituted, so it behaves like an acid.

10
09. [Din.B’23]

(c) Write the preparation of alcohol from compound B with equations. 3

(d) B and C of the stem show different type of addition reaction- analyze. 4
Answer
(c) Complete form of the reaction in the stem:

We know, alcohol is produced if aldehyde is reduced

LiAlH4
CH3 − CHO → CH3 − CH2 − OH
2 [H]

(d) According to stem, B is CH3 CHO and C is CH2 = CH2 .

Both B and C of the stem give addition reaction. But B gives nucleophilic addition reaction and C gives
electrophilic addition reaction.
Nucleophilic addition reaction:
In aldehyde or ketone having bivalent carbonyl radical, nucleophilic addition reaction occurs. The pi (𝜋)
electron of carbonyl radical is attracted more towards the Oxygen atom as the difference of
electronegativity between carbon and oxygen is (3.5 − 2.5 = 1.0). As a result, partial negative (δ− ) charge
is formed in oxygen atom and partial positive δ+ ) charge is formed in carbon atom . In this way,
the negative nucleophilic reagent or the nucleophile easily attacks positive carbon atom of polarized
carbonyl radical and causes nucleophilic addition reaction. In this case, cyanide ion (CN − ) (form HCN),
sodium sulphite ion ( −OSO2 Na) (from NaHSO3), molecule, grignard reagent and carbanion
act as nucleophile.
Electrophilic addition reaction: It is essentially a characteristic reaction of alkynes and alkenes. In this
case, the pi electron of the carbon-carbon double bond (C = C) acts as an electron donor to the electrophile
or electron-withdrawing reagent. Then reagents such as: Cl2 , Br2 , HCl etc. react under the effect of electrons
in the solution.
𝐇𝟐 𝐅𝐞 𝐭𝐮𝐛𝐞
10. (i) 𝐂𝐚𝐂𝟐 + 𝟐𝐇𝟐 𝐎 → 𝐗 + 𝐂𝐚(𝐎𝐇)𝟐 (ii) 𝐘 ← 𝐗→ 𝐙 [MB’23; DB’22]
𝐏𝐝, 𝐁𝐚𝐒𝐎𝟒 𝟒𝟓𝟎°𝐂
(c) How the elements in the gas mixture of X and Y can be separated? Write with equations. 3
(d) Whether Y and Z compound in the stem give similar type of reaction or not- analyze. 4
Answer
(c) Completing the two reactions we get,
(i) CaC2 + H2 O → CH ≡ CH + Ca(OH)2
H2 Fe tube
(ii) CH2 = CH2 ← CH ≡ CH →
Pd, BaSO4 450℃

11
 Here, X is ethyne and Y is ethene. Though X (ethyne) produces white ppt. of alkynide by reacting upon
addition of ammonia with silver in the mixture of X and Y gas, Y doesn’t react.
CH ≡ CH + 2[Ag(NH3 )2 ]NO3 → Ag. C ≡ C. Ag(s) +NH4 NO3 (aq) + NH3 (g)
Silver alkynide (white)
CH2 = CH2 + [Ag (NH3 )2 ]NO3 → No Reaction
In other way, if Na, dissolved in liquid ammonia, is mixed with the mixture of X and Y gas, Hydrogen gas
is produced along with sodium alkynide. But Y (ethene) doesn’t react in this case
Liquid NH3
CH ≡ CH(g) + 2Na(s) → Na. C ≡ C. Na(s) + H2 (g)
Hydrogen gas
Liquid NH3
CH2 = CH2 + Na → No Reaction
In this way, X and Y can be separated.
(d) Reactions of the stem,
CaC2 + 2H2 O → CH ≡ CH + Ca(OH)2
(X)

H2 Fe tube
CH2 = CH2 ← CH ≡ CH →
Ethene(Y) Pd.BaSO4 Ethyne (X) 450°C
benzene (Z)
Y is ethene Unsaturated hydrocarbon
Z is benzene Shows special type of unsaturation
It is an unsaturated hydrocarbon due to the presence of double bonds in benzene. But it does not react as
rapidly as ethene or ethyne, despite the presence of three double bonds in the benzene molecule. While
benzene forms compounds with by reacting with H2 , X 2 and O3 , but it doesn’t form any additive compounds
with HCl, HBr, H2 SO4 , R − X. Even it doesn’t show unsaturation test, bayer test and bromine solution test.
So, unsaturation of Z compound between Y and Z is different. It shows special type of unsaturation.
11. [RB’22]

(d) Show with suitable mechanisms that compound (C) obeys Markovnikov’s rule. 4
Answer
(d) C compound is butene-1 (CH3 − CH2 − CH = CH2 ). According to Markovnikov’s rule, in the reaction of
an asymmetrical reagent with an asymmetrical alkene the H or positive end of the reagent is preferentially
attached to the carbon atom that has more H atoms in the double bond of the alkene.
Here compound C, butene-1(CH3 − CH2 − CH = CH2 ) is an asymmetrical alkene. The reaction of the
asymmetrical reagent HX with it obeys the Markovnikov’s rule.
Considering HBr as HX and completing the reaction-
Br
+ Br− |
+ CH3 − CH2 − CH − CH3 → CH3 − CH2 − CH − CH3 (90%)
−
CH3 CH2 − CH = CH2 + H Br →
+ Br−
CH3 − CH2 − CH2 − CH2 → CH3 − CH2 − CH2 − CH2 Br(10%)
So, C (alkene-1) obeys Markovnikov’s rule.

12
12. Observe the following stem and answer the questions: [Ctg.B’22]

(d) Between ‘A’ and ‘B’ compound which one follows the Markovnikov’s rule? Explain. 4
Answer
(d) Similar to the (d) of board question no. 11, T-02. Answer: Between A and B, B (Butene-1) is an
asymmetric alkene. Thus, B obeys the Markovnikov’s rule.

13. Two compound A and B have molecular formula of 𝐂𝟓 𝐇𝟏𝟎 & 𝐂𝟓 𝐇𝟖 respectively. [SB’22]
(c) 𝐇 − 𝐂𝐇𝐎 & 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐂𝐇𝐎 is produced though ozonolysis and hydrolysis of the
compound ‘A’ in the stem. Write down the structure and name of compound A with proper
reactions. 3
(d) Among the possible isomers of compound B, which one will show acidic nature? Explain with
quations. 4
Answer
(c) The compound A is C5 H10 .
Through ozonolysis and hydrolysis HCHO and CH3 − CH2 − CH2 − CHO is produced. The reaction is given below:
H2 O
CH3 − CH2 − CH2 − CH = CH2 + O2 → CH3 − CH2 − CH2 − → CH3 − CH2 − CH2 − CHO + HCHO
Pentene−1 CCl4 Zn,∆

That is, the compound is pentene-1. Structure, CH3 − CH2 − CH2 − CH = CH2
Since, the alkene will break into methanal and butanal, so the carbon number of the alkene will be 5 and the
double bond will be in 1 no. carbon.
(d) Possible isomers of B (C5 H8 )
5 4 3 2 1
CH3 − CH2 − CH2 − C ≡ CH Pentyne-1
5 4 3 2 1
CH3 − CH2 − C ≡ C − CH3 Pentyne-2
4 3 2 1
CH3 − CH − C ≡ CH 3 methylbuteyne-1
|
CH3

Since, alkyne-1 is acidic, among them, pentyne-1 is more acidic.

The compound that release (H + ) proton, are acidic.
In the 1 and 2 no. carbon of pentyne-1, there are 1 sigma bond and 2 bonds. For which, bond is very strong.
Therefore, the sigma bond between 1 no. carbon and H becomes weak. So, the bond breaks easily, that is it
can give proton easily for which it is acidic. Among pentyne-1 and 3-methyl butyne-1, conjugate base of
pentyne-1 more stable because of resonance. On the other hand, 3-methylbutyne’s conjugate base is not
stables because it has steric effect contain -1ng −CH3 group and because of all these, the alkyne-1 is more acidic.

13
14. Two isomers of 𝐂𝟒 𝐇𝟖 are A (symmetric) and B (asymmetric). The compound B produces ‘C’ by
reacting with HBr. [SB’22]
(c) Discuss the process of preparing compound C from compound B of the stem. 3
(d) The compound A and C of the stem show two different isomerism – Explain it. 4
Answer
(c) Similar to the (d) of board question no. 11, T-02
Br
|
Answer: B: CH3 − CH2 − CH = CH2, C: CH3 − CH2 − CH − CH3
(d) Similar to the (d) of board question no. 03, T-01
Answer: A= Geometric isomerism, C = Position and chain isomerism.
15. [JB’22]

(d) Which one will be the main product in the addition reaction of compound A and HX? Explain in
light of the associated principle. 4
Answer
(d)

Compound A is Propene.
In the addition reaction of Propene with HX, the compound will be produced according to the
Markovnikov’s rule.
Mechanism: (Electrophilic Addition reaction)

In first step, H + ion and X − ion is produced. Carbocation is formed first by the H + ion and later, halide is
formed by the addition of X − to the carbocation.
16. [JB’22]

(c) Write down the preparation of ‘𝐁’ from ‘𝐀’ with equations. 3
(d) Which one is acidic between A and C? Analyze. 4
Answer
(c) Completing the reaction we get,

14
 Hydration of acetylene in 2% HgSO4 (Mercuric sulfate) and 20% H2 SO4 acid mixture produces aldehyde
and in case of other alkynes, produces ketone.

(d) A is CH ≡ CH and C is CH2 = CH2. Between them A is more acidic. The remaining part is similar to (d) of board
question no. 01, T-02.

17. [Din.B’22]

(d) Which one is acidic between ‘A’ and ‘B’? Analyze. 4

Answer
(d) According to stem, compound ‘A’ is ethyne and compound ‘B’ is ethene. Between these, compounds ‘A’
that is ethyne is acidic in nature. The remaining part is similar to the (d) of board question no: 01, T-02.

18. [JB’21]
R _ CH2 _ CH2Br(10%)
R _ CH=CH2
R _ CH_ CH3(90%)
Br
(c) How to produce 90% product in the given equation? Explain. 3
(d) Analyze the given equation to find the process required to convert 10% product to 90% product. 4
Answer
(c) Given equation:

According to Markovnikov's principle, "In the reaction of an asymmetrical reagent with an asymmetrical
unsaturated compound, the negative part of the reactant molecule will be attached to the carbon atom with
fewer H atoms."
According to this principle, in the reaction of asymmetric reagent HBr with alkyne-1, the negative part (Br − )
of HBr is attached to the carbon with less number of H atoms i.e. the 2nd carbon atom on the side of alkyne-
1 and the positive part or hydrogen ion added to the 1st carbon to give 90% of the major product 2° alkyl
bromide.

15
(d) Using organic peroxide to convert 10% product to 90% product in the given equation is called Kharas' principle.

This addition reaction is accomplished through free radical mechanism.

Introduction:
Step 1: Fission of peroxide produces free alkoxy radical.
∆
R − O − O − R → 2R − O
Step 2: The resulting free radical reacts with HBr to produce bromine free radical.
R −O +HBr → R − OH + Br
Spread:
Step-3: The free radical attaches to the C atom between two of the double-bonded carbon atoms of the
asymmetric alkyne to form a more stable free radical.

R _ CH_ CH2(1°)
Br
R _ CH=CH2 Br

R _ CH_ CH2Br(2°)
Step-4: Reaction of HBr with the more stable 2° free radical will form the 1° bromoalkane.

Termination: Br + Br Br2

19. [Din.B’21]

𝐀𝐥𝐤𝐲𝐥 𝐇𝐚𝐥𝐢𝐝𝐞 𝐨𝐟 𝐭𝐰𝐨 𝐜𝐚𝐫𝐛𝐨𝐧

(𝐀)
(c) Write the equations of the reactions to test the unsaturation of compound C. 3
(d) Write the mechanism for the preparation of compound B from compound A. 4
Answer
(c) The equation we get from A and C is
KOH(alc)
CH3 CH2 X → CH2 = CH2 + KX + H2 O
(A) (C)

Remaining part is similar to the (c) of board question no. 02, T-07.
(d) The mechanism for the preparation of compound B from compound A is similar to the (c) of board
question no: 07, T-03.

16
20. [DB’19]
CaC2 + H2O A + Ca(OH)2
H2(Pd + BaSO4)
B
(c) How can you produce an aromatic compound from ‘A’? Describe. 3
(d) Which is more acidic between 'A' and 'B'? Analyze. 4
Answer
(c) Preparation of aromatic compound from A is similar to the (c) of board question no. 15, T-07.
(d) Similar to the (d) of board question no. 01, T-02, A is CH ≡ CH and B is CH2 = CH2
𝐏𝐝, 𝐁𝐚𝐒𝐎𝟒 𝐎𝟑
21. 𝐀→ 𝐁→ 𝐂 + 𝐃 + 𝐙𝐧𝐎 ; ‘A’ is three carbon alkyne. [RB’19]
𝐇𝟐 𝐙𝐧
(c) Describe the differentiating experiment of A and B with reaction. 3
Answer
Pd+BaSO4
(c) CH3 − C ≡ CH + H2 → CH3 − CH = CH2
B
Differentiating reaction of alkene and alkyne are shown below:
KMnO4
(i) CH3 − C ≡ CH + [O] → CH3 − COOH + CO2
KOH
OH OH
KMnO4 | |
CH3 − CH = CH2 + [O] → CH3 − CH − CH2
KOH
When KMnO4 solution is passed through propene the propylene glycol is produced and when it is passed
through propyne then ethanoic acid and CO2 is produced.
Br Br
CCl4
| |
(ii) CH3 − C ≡ CH + Br2 → CH3 − C − C H
| |
Br Br
1,1,2,2−tetrabromo propane
Br Br
CCl4 | |
CH3 − CH = CH2 + Br2 → CH3 − C − CH2
1,2−dibromo propane
(iii) CH3 − C ≡ CH + [Ag(NH3 )2 ]NO3 ⇒ CH3 − C ≡ CAg ↓ + NH4 NO3 + H2 O
white
CH3 − CH = CH2 + [Ag(NH3 )2 ]NO3 → No reaction
(iv) CH3 − C ≡ CH + [Cu(NH3 )2 ]Cl2 → CH3 − C ≡ CCu ↓ + NH4 Cl + H2 O
red
CH3 − CH = CH2 + [Cu(NH3 )2 ]Cl2 → No reaction
o o
O Zn ∥ ∥
(v) CH3 − C ≡ CH + O3 → CH3 − C C H +H2 O → CH3 − C − C − H
O O
O Zn
CH3 − CH = CH2 + O3 → CH3 − CH C H2 +H2 O → CH3 CHO + HCHO
O O

17
 𝐏𝐂𝐥𝟓 𝐏𝐝
22. 𝐂𝐇𝟑 − 𝐂𝐎𝐎𝐇 → ′𝐗′ → ′𝐀′ + 𝐇𝐂𝐥 [SB’19]
𝐁𝐚𝐒𝐎𝟒
𝐏𝐂𝐥𝟓 𝐏𝐝
𝐂𝐎𝐎𝐇 → ′𝐘 ′ → ′𝐁′ + 𝐇𝐂𝐥
𝐁𝐚𝐒𝐎𝟒
(c) How will you prepare ‘A’ from ethyne? Write with equations. 3
Answer
PCl5 Pd(H2 )
(c) CH3 COOH → CH3 COCl → CH3 CHO + HCl
X BaSO4 (A)
20% H2 SO4 rearrangement
CH ≡ CH + H − OH → CH2 = CH → CH3 CHO
ethyne 2% HgSO4 |
OH

Thus, if ethyne is hydrolyzed by H2 O in presence of 20% H2 SO4 and 2% HgSO4, then compound A, that
is, CH3 CHO is produced.
23. An organic reaction: [BB’19]
𝐂𝐇𝟑 𝐂𝐇𝟑
| |
𝐂𝟐 𝐇𝟓 − 𝐂 = 𝐂𝐇𝐂𝐥 + 𝐇𝐂𝐥 → 𝐂𝟐 𝐇𝟓 − 𝐂 − 𝐂𝐇𝟐 𝐂𝐥
(𝐀) |
𝐂𝐥
(𝐁)

(c) Explain the mechanism of the above reaction. 3

Answer
(c) The reaction in the above stem has taken place following Markovnikov’s rule.
CH3 CH3
| |
C2 H5 − C = CHCl + HCl → C2 H5 − C − CH2 Cl
|
Cl
At first heterolytic fission of HCl occurs and produces H + & Cl . Then H + ion attacks A compound and
−

produces 1° & 3°carbocation.

HCl → H + + Cl

CH2
|
C2 H5 − C = CHCl + H +

But the order of the stability of carbocation is 3° > 2° > 1° and so 3° carbocation is more stable. As a result,
Cl− will react with it.
CH3 CH3
| |
C2 H5 − C − CH2 Cl + Cl− → C2 H5 − C − CH2 Cl
⨁ |
Cl
This is how, the reaction takes place by following Markovnikov’s rule.
24. [JB’19]
𝐑𝐌𝐠𝐗 𝐙𝐧𝐂𝐥𝟐 +𝐇𝐂𝐥
𝐂𝐂𝐥𝟒 𝐙𝐧,𝐇𝟐 𝐎
C →+ 𝐄→ 𝐰𝐡𝐢𝐭𝐞 𝐩𝐫𝐞𝐜𝐢𝐩𝐢𝐭𝐚𝐭𝐞 (𝐟𝐚𝐬𝐭)
𝐇 /𝐇𝟐 𝐎
𝐀 + 𝐎𝟑 → 𝐁→ 𝐑𝐌𝐠𝐗 𝐙𝐧𝐂𝐥𝟐 +𝐇𝐂𝐥
D 𝐇→+/𝐇 𝐎 𝐅 → 𝐰𝐡𝐢𝐭𝐞 𝐩𝐫𝐞𝐜𝐢𝐩𝐢𝐭𝐚𝐭𝐞 (𝐀𝐟𝐭𝐞𝐫 𝟓 − 𝟏𝟎 𝐦𝐢𝐧)
𝟐
(c) Explain the formation of A compound with reactions. 3

18
 Answer
(c) E and F of the stem reacts with Lucas reagent so they are alcohols. Since E reacts fast so E is 3° alcohol and
F takes 5-10 minutes to react so it is 2° alcohol. Again, to form E, ketone is to react with Grignard reagent,
so C is ketone. To form F, except for methanal any aldehyde is to react with Grignard reagent, so D is any
aldehyde except methanal. As a result, A is such an alkene which reacts with ozone and after hydrolysis
forms an aldehyde and ketone.
R H
C=C
R R
A
R H R O H
Zn
C=C + O3 C C +H2 O → R′ − CO − R" + RCHO + ZnO
C D
R R R O O R
A
OH Cl
RMgx
| ZnCl2 |
R′ − CO − R′′ + → + R′ − C − R′′ + → R′ − C − R” ↓
H /H2 O HCl white
| | precipitate
R R
(E)
OH Cl
RMgx
| HCl
|
RCHO + → R − C − R + ZnCl2 → R−C−R↓
D H2 O/H+
| |
H H
(F)
R H
C=C
R R
A

T-03: Alkyl halide and 𝐒𝐍 𝟏, 𝐒𝐍 𝟐, 𝐄𝟏 , 𝐄𝟐

01. [Ctg.B’23]

(d) Will the mechanism of both reactions in the stem be similar? Analyze. 4
Answer
(d) Completing the reaction, we get:

Reaction no. (i) of stimulus is substitution reaction and reaction no. (ii) is elimination reaction. The
mechanisms of the two reactions are different:

19
 In no. (i) the reaction takes place mainly in the SN 2 mechanism. The reaction occurs in one step. When the
nucleophile attacks the partially positive carbon atom opposite to the Cl atom of C3 H7 Cl, a new covalent
bond is formed and the old C-Cl bond is broken to form an intermediate complex.
Finally, the C-Cl bond is broken and the Cl− ion is released and the nucleophile becomes fully covalently bound
to the C atom. Then the structure of the product molecule is inverted with the other three atoms freed from the C
atom or like an inverted umbrella in a fundamental storm and obtains a new three-dimensional structure.

On the other hand reaction (ii) is E2 reaction which also takes place in step one. In this reaction, the effect
of alkali is to simultaneously remove an H + from the β carbon and the leaving group halide ion (Cl− ). As a
result, the electron pairs of β carbon are arranged between α and β carbons and carbon-carbon double bonds are formed.

Therefore, observing the reactions it can be understood that mechanism of reactions (i) and (ii) will be
different.
𝐡𝛎
02. 𝐂𝐧 𝐇𝟐𝐧+𝟐 → 𝐂𝐧 𝐇𝟐𝐧+𝟏 𝐂𝐥 →𝐊𝐎𝐇(𝐚𝐪) 𝐑 [JB’23]
𝐏
[𝐧=𝟏]
𝐂𝐥𝟐 𝐐
(d) Analyze the mechanism of preparing compound R from Q of the stem. 4
Answer
(d) Completing the reaction we get,
hν KOH
CH4 → CH3 Cl → CH3 OH
Cl2
In aqueous KOH solution, OH − ion acts as nucleophile. In this case by OH − (SN 2) reaction, CH3 OH
compound is produced.
SN 2 means bi molecular nucleophilic substitution where CH3 Cl and KOH both have active role. The reaction
is of 2nd order and completed in one step. The reaction figure is shown below:

𝐇𝐁𝐫
03. 1. 2-Methyl butene-1 → 𝐀(𝟗𝟎%) + 𝐁(𝟏𝟎%) [CB’23]
(𝐦𝐚𝐣𝐨𝐫 𝐩𝐫𝐨𝐝𝐮𝐜𝐭) (𝐦𝐢𝐧𝐨𝐫 𝐩𝐫𝐨𝐝𝐮𝐜𝐭)
𝐍𝐚𝐎𝐇(𝐚𝐪)
2. A compound → 𝐂 compound
(c) Show the reaction mechanism of preparing compound C of the stem from compound A. 3
Answer
(c) If the reaction of the stem is completed:

20
 Here, according to Markovnikov’s rule, A will be major product and B will be minor product.

The reaction will be completed in SN 1 mechanism since it is 3° alcohol.

1st step: Breaking of bond with halogen:

2nd step: Nucleophile substitution:

Over all reaction:

04. [RB’22]
Compound-A 𝟑° alkyl halide (i) 𝐀 + 𝐍𝐚𝐎𝐇 (𝐚𝐪) → 𝐂 + 𝐍𝐚𝐂𝐥
Compound-B 𝟏° alkyl halide (ii) 𝐁 + 𝐍𝐚𝐎𝐇 (𝐚𝐪) → 𝐃 + 𝐍𝐚𝐂𝐥
(d) Discuss the mechanism of the reaction no. (i) of stem. 4
Answer
(d) Reaction no-1 of stimulus is Nucleophilic substitution (SN 1) reaction similar to the (c) of board question no. 03,
T-03.
05. Observe the following stem and answer the questions: [Ctg.B’22]

(c) Which mechanism is followed to produce ‘M’ compound of the stem? Explain. 3
Answer
(c)

(M compound is produced through Nucleophilic substitution reaction)

21
06. [Din.B’22]

(i)

(ii)

(c) Describe the reaction mechanism of reaction (i) in stem. 3

Answer
(c) Similar to the (c) of board question no. 03, T-03, Mechanism: SN 1

07. 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐁𝐫 + 𝐊𝐎𝐇(𝐚𝐪) → 𝐘 + 𝐊𝐁𝐫. [MB’22]

(c) Explain the mechanism of the reaction of the stem. 3
(d) Is it possible to obtain alkene from Y- compounds? Explain with logic. 4
Answer
(c) CH3 − CH2 Br + KOH(aq) → CH3 − CH2 OH + KBr
OH − ion acts as nucleophile in aqueous KOH solution. In this case OH − forms CH3 − CH2 − OH compound
through SN 2 reaction.
Mechanism:

(d) Compound Y is an alcohol (CH3 − CH2 − OH) CH3 − CH2 − OH can produce alkene by dehydration process.
180℃
CH3 − CH2 − OH + H2 SO4 → CH2 = CH2 + H2 O + H2 SO4
350−400℃
Or, CH3 − CH2 − OH → CH2 = CH2 + H2 O
Al2 O3

Its mechanism is described below:

Step-1:
Step-2:

08. (𝐢) 𝐑 𝟑 𝐂𝐗 + 𝐍𝐚𝐎𝐇 (𝐝𝐢𝐥𝐮𝐭𝐞) → 𝐀, 𝐗 = Halogen

(𝐢𝐢) 𝐑𝐂𝐇𝟐 𝐗 + 𝐍𝐚𝐎𝐇 (𝐜𝐨𝐧𝐜) → 𝐁 [DB’21]
(d) Analyze the mechanism of the preparation of B compound in the stem. 4
Answer
(d) Mechanism of preparation of compound ‘B’ is similar to the (c) of board question no. 07, T-03.

22
09. Answer the following questions according to the stem: [RB’21]
𝐂𝐇𝟑
|
(i) 𝐂𝐇𝟑 − 𝐂 − 𝐂𝐥 + 𝐍𝐚𝐎𝐇(𝐚𝐪) → 𝐏 + 𝐍𝐚𝐂𝐥
|
𝐂𝐇𝟑

𝐂𝐂𝐥𝟒
(ii) +𝐎𝟑 → 𝐀+𝐁
𝐙𝐧,𝐇𝟐 𝐎

(c) Discuss the mechanism of reaction of preparation of P. 3

Answer

(c) Similar to the (c) of board question no: 03, T-03. Here,

𝐜𝐨𝐦𝐩𝐥𝐞𝐭𝐞 𝐨𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
10. 𝐑 𝟑 𝐂 − 𝐗 + 𝐊𝐎𝐇 (𝐚𝐪) → 𝐀 → 𝐁 [CB’21]
(c) Explain the reaction mechanism to produce A. 3

Answer

(c) The mechanism of preparation of A is similar to the (c) of board question no: 03, T-03.

𝐇𝟐 𝐎 𝐅𝐞 𝐭𝐮𝐛𝐞 𝐚𝐧𝐡𝐲𝐝𝐫𝐨𝐮𝐬 𝐀𝐥𝐂𝐥𝟑

11. 𝐂𝐚𝐂𝟐 → M (gas) → 𝐍→ 𝐋 [Ctg.B’19]
𝟒𝟓𝟎°𝐂 𝐂𝐇𝟑 𝐂𝐥

(c) Describe the reason of acidity of compound ‘M’. 3

Answer

(c) CaC2 + H2 O → Ca(OH)2 + CH ≡ CH

M

Ethyne is alkyne-1 which is slightly acidic. Basically, hybridization of C in ethyne is sp, for which bond
length of C − C is comparatively less which is 1.20Å. Again, due to increase of property of s-orbital in
hybridized orbital, electronegativity of C increases. So, in sp hybridization electronegativity of carbon is
more. For which shared electron of C − H bond comes towards carbon more as C − C bond length is less.
As a result, C-H bond becomes weak and as H remains at the end so H is easily replaced. Thus by donating
proton ethyne acts as acid.
CH ≡ CH + [Ag(NH3 )2 ]NO3 → AgC ≡ CAg ↓ + NH4 NO3 + NH3
(red)

CH ≡ CH + [Cu(NH3 )2 ] Cl → CuC ≡ CCu ↓ + NH4 Cl + NH3

(white)

∴ Here, H from ethyne is replaced and thus it acts as an acid.

So, in sp hybridization due to high electronegativity of carbon and C-C short bond length and replacable
hydrogen of ethyne, it is acidic.

23
12. (i) (𝐂𝐇𝟑 )𝟑 𝐂𝐗 + 𝐝𝐢𝐥𝐮𝐭𝐞 𝐛𝐚𝐬𝐞 (𝐚𝐪) → ‘𝐀’ [All B’18]
(ii) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐗 + 𝐬𝐭𝐫𝐨𝐧𝐠 𝐛𝐚𝐬𝐞 (𝐚𝐪) → ‘𝐁’
(d) Analyze whether the reaction mechanisms of the reactions in the stem are similar or not. 4
Answer
(d) Reaction mechanism of (i) is SN 1 although that of (ii) is SN 2.
𝐒𝐍 𝟏 mechanism:
In reaction (i) nucleophilic substitution occurs in 2 steps. But it occurs easily in case of 3° halide. It is a 1st
order reaction & there is formation of carbo-cation, geometric structure remains unchanged; Transition state
is not formed.
CH3 CH3
| slow |
1st step: CH3 − C − Cl → CH3 − C + + Cl−
| |
CH3 CH3
CH3 CH3
| fast |
2nd step: CH3 − C+ + OH − → CH3 − C − OH
| |
CH3 CH3
𝐒𝐍 𝟐 mechanism:
Reaction (ii) which is a nucleophilic substitution reaction that occurs in 1 step. The reaction rate depends on
concentration of both halogeno alkane & nucleophilic reagent. It is a 2nd order reaction & there is no
formation of carbo-cation or anion; transition state is formed; geometric structure is completely different.

T-04: Alcohol and Ether

01. [RB’23]

𝐀 = 𝐂𝟒 𝐇𝟗 𝐗
𝐌 = 𝟑 carbon containing carbonyl compound which doesn’t reduce Tollen's reagent.
(c) How compound P of the stem can be prepared from Grignard reagent? Write with reactions. 3
Answer
(c)

3°alcohol
Preparation of 3° alcohol from Grignard reagent:

Mechanism:

3°alcohol
That means, 3° alcohol can be prepared from by reaction of grignard reagent with ketone.

24
 𝐎𝟑 𝐙𝐧,∆
02. 𝐀 (2-methyl-but-2-ene) → ozonide compound → 𝐁 + 𝐂 +ZnO (Compound B doesn’t react
𝐂𝐂𝐥𝟒 𝐇𝟐 𝐎
with Tollen’s reagent). [Ctg.B’23]
(c) Explain the preparation of 𝟐°-alcohol from compound B of the stem with reactions. 3
Answer
(c) Completing the reaction:

2° alcohol is produced from the reaction of grignard reagent and CH3 CHO.
CH3 H
dry ether | − + H2 O |
RMgX + CH3 CHO → R − C − OMgX → R − C − OH + Mg(OH)X
| |
H CH3
2° alcohol
[Here, X = element of halogen group and R=alcohol group]
03. [Ctg.B’23]

(c) Show the identification test of functional group in compound A of the stem with reactions. 3
Answer
KOH (aq)
(c) C3 H7 Cl → C3 H7 OH + HCl
A
A is an alcohol.
Identification of alcohol:
(i) Test with Na metal: H2 gas is produced in the reaction of alcohol with Na metal dissolved in inactive
solvent ether.
1
CH3 − CH2 − CH2 OH + Na → CH3 − CH2 − CH2 ONa + 2 H2 ↑
(ii) Reaction with PCl5 : If alcohol dissolved in ether or benzene is reacted with PCl5 , HCl is emitted and
the emitted gas produces white fume of NH3 .
CH3 − CH2 − CH2 OH + PCl5 → CH3 − CH2 − CH2 Cl + POCl3 + HCl
HCl + NH3 → NH4 Cl (White fume)
𝐊𝐎𝐇(𝐚𝐪) [𝐎] [𝐎]
04. 𝐘→ 𝐙→ 𝐌→ 𝐓 [SB’23]
𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 & 𝐇𝟐 𝐒𝐎𝟒 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 & 𝐇𝟐 𝐒𝐎𝟒
𝐓 = Monocarboxylic acid with 3 carbons.
(c) How will you identify functional group of compound Z? Describe with equations. 3
Answer
(c) Completing the reaction, we get:

Z is alcohol. Remaining part is similar to the (c) of board question no. 03, T-04.

25
05. [SB’23]

(c) How will you prepare alcohol from compound Y? Write with reactions. 3
Answer
(c) RX is alkyl halide. If “R − MgX produces 2°
Mg
RX → RMgX (Grignard reagent) alcohol by reacting with
Dry ether CH3CHO, it will also be correct
1° alcohol is produced in the reaction of HCHO with Grignard reagent.

06. [Din.B’23]

(c) Write the identification test of compound D. with reaction. 3

Answer
(c) Completing the reaction of the stem we get,
KOH
CH3 CHClCH3 → CH3 CHCH3 (D) + KCl
|
OH
2° alcohol

Identification of alcohol is similar to the (c) of board question no. 03, T-04.
07. [RB’22]
Compound-A 𝟑° alkyl halide (i) 𝐀 + 𝐍𝐚𝐎𝐇 (𝐚𝐪) → 𝐂 + 𝐍𝐚𝐂𝐥
Compound-B 𝟏° alkyl halide (ii) 𝐁 + 𝐍𝐚𝐎𝐇 (𝐚𝐪) → 𝐃 + 𝐍𝐚𝐂𝐥
(c) Write the difference between compounds C and D with reactions. 3
Answer
(c)

26
 Lucas reagent test can distinguish between C and D.

dry ZnCl2
conc. HCl

dry ZnCl2
→
conc. HCl

08. Consider the stem and answer the following questions: [Ctg.B’22]
𝐙𝐧−𝐇𝐠
(i) '𝐗 ′ 𝐂𝐨𝐧𝐜.𝐇𝐂𝐥 𝐂𝐇𝟑 − 𝐂𝐇𝟑 + 𝐇𝟐 𝐎
𝐙𝐧−𝐇𝐠
(ii) '𝐘 ′ 𝐂𝐨𝐧𝐜.𝐇𝐂𝐥 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟑 + 𝐇𝟐 𝐎
(c) How can you produce a 2° alcohol from ‘X’ compound? Show with equations. 3
Answer
(c) 2° Alcohol can be produced from the reaction between Grignard nearest and X CH3 CHO). Remaining part
is similar to the (c) of board question no. 02, T-04.

09. [JB’22]

(c) Which is produced by the strong oxidation of compound-B? Show with equations. 3
Answer
(c) Completing the reaction we get,

Here, compound B is Propanol.

Propanoic acid is produced by the strong oxidation of Propanol.

10. (𝐢) 𝐑 𝟑 𝐂𝐗 + 𝐍𝐚𝐎𝐇 (dil) → 𝐀 , X= Halogen [DB’21]

(𝐢𝐢) 𝐑𝐂𝐇𝟐 𝐗 + 𝐍𝐚𝐎𝐇 (conc) → 𝐁
(c) Describe the differences between A and B compound with reaction. 3
Answer
(c) Similar to the (c) of board question no. 07, T-04. A = 3° Alcohol, B = 1° Alcohol.

27
 𝐜𝐨𝐦𝐩𝐥𝐞𝐭𝐞 𝐨𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
11. 𝐑 𝟑 𝐂 − 𝐗 + 𝐊𝐎𝐇 (𝐚𝐪) → 𝐀 → 𝐁 [CB’21]
(d) Discuss the identification reaction of functional groups of A and B. 4
Answer
(d) From 'c' we get, A is alcohol (R 3 C − OH) and B is carboxylic acid (R − COOH). The reaction for
identification of alcohol functional group (−OH) and carboxylic acid functional group (−COOH) is as
follows:
−OH group Identification:
(1) Test with metallic Na: If any organic compound dissolved in pure organic compound or inert solvent,
ether reacts with Na metal and produces H2 , it is proved that the organic compound has −OH group.
∆
2R − OH + 2Na → 2R − ONa + H2 ↑
(2) Test with 𝐏𝐂𝐥𝟓 : If any organic compound dissolved in anhydrous organic compound or inert ether
solvent is heated with PCl5 , HCl gas is evolved and the evolved gas forms white fumes of NH4 Cl on
contact with a glass rod wet with NH3 , then the compound is alcohol (− OH).
R − OH + PCl5 → R − Cl + POCl3 + HCl
HCl + NH3 → NH4 Cl (white fume)
−COOH group identification:
(1) Litmus test: Organic acids ionize in aqueous solution to produce H + . So organic acids turn blue litmus
into red in aqueous solution.
R − COOH + H2 O = RCOO− + H3 O+
H3 O+ + Blue litmus → Red litmus + H2 O
(2) 𝐍𝐚𝐇𝐂𝐎𝟑 solution test: Reaction of 5% NaHCO3 solution with organic acid containing −COOH group
produces CO2 with bubbles. The CO2 gas released makes the lime water [Ca(OH)2 ] turbid.
R − COOH + NaHCO3 → RCOONa + H2 O + CO2
CO2 + Ca(OH)2 → CaCO3 ↓ +H2 O
𝐝𝐫𝐲 𝐞𝐭𝐡𝐞𝐫
12. (i) 𝐑 − 𝐈 + 𝐌𝐠 → 𝐀 [SB’21, Din.B’21]
𝐢𝐬𝐨𝐦𝐞𝐫𝐢𝐳𝐚𝐭𝐢𝐨𝐧
(ii) 𝐂𝟐 𝐇𝟔 𝐎(𝐁) → 𝐂
(c) Write down the difference between compounds B and C with equations. 3
(d) Write down the equation for the preparation of 1°, 2° and 3° alcohols from compound A. 4
Answer
(c) Here B is CH3 CH2 OH and C is CH3 − O − CH3
CH3 CH2 OH reacts with PCl5 and produces HCl gas but CH3 − O − CH3 does not produce HCl when reacting
with PCl5 .
CH3 CH2 OH + PCl5 → CH3 CH2 Cl + POCl3 + HCl; HCl + NH3 ⟶ NH4 Cl (white fumes)
B
CH3 − O − CH3 + PCl5 → 2CH3 − Cl + POCl3
(d) Here A is R-MgI (Grignard’s Reagent)
dry
R − I + Mg → R − MgI
ether
Preparation of 1°, 2° 3° alcohol from Grignard’s Reagent:
R
| H2 O
(i) R − MgI + H − C = O → H − C − OMgI → R − CH2 − OH + Mg(OH)I
| | ∆
H H
1° alcohol

28
 R CH3
| H2 O |
(ii) R − MgI + CH3 − C = O → CH3 − C − OMgI → R − CH − OH + Mg(OH)I
| | ∆
H H

2° alcohol
R R
| H2 O |
(iii) R − MgI + CH3 − C = O → CH3 − C − OMgI → CH3 − C − OH + Mg(OH)I
| | ∆ |
CH3 CH3 CH3
3° alcohol

13. [MB’21]
1.HCHO 2.H2O,H+
X
1.CH3CHO 2.H2O,H+
CH3MgI Y
1.CH3COCH32.H2O,H+
Z
(c) Explain the reaction to form ether from ′𝐗′ compound. 3
(d) Explain the order of the reactivity of 𝐗, 𝐘and 𝐙 with reason using Lucas reagent. 4
Answer
(c) Here X molecule is CH3 CH2 OH
Formation of ether from 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐎𝐇:
Ether is produced in the reaction of excess CH3 CH2 OH with concentrated Sulphuric acid.
CH3 CH2 OH + H2 SO4 (conc. ) → CH3 CH2 OSO3 H + H2 O
CH3 CH2 OSO3 H + CH3 CH2 OH → CH3 − CH2 − O − CH2 − CH3 + H2 SO4
(d) In the stem, X is CH3 CH2 OH (1°)
CH3
|
Y is CH3 − CH − OH(2°) ; Z is CH3 − C − OH(3°)
| |
CH3 CH3
Z reacts instantaneously with Lucas reagent. Y gives the reaction in 5 − 10 minutes and forms halide and
X forms halide after heating for a long time.
ZnCl2 ,25°C
(CH3 )3 C − OH + HCl → (CH3 )3 C − Cl + H2 O
Fast
ZnCl2 ,25°C
(CH3 )2 CH − OH + HCl → (CH3 )2 CH − Cl + H2 O
5−10min
ZnCl2
CH3 CH2 OH + HCl → CH3 − CH2 Cl + H2 O
very slow
So, the order of reactivity of X, Y and Z is: Z > Y > X
14. [MB’21]

Both A and B contains carbonyl group.

(c) Prepare ester from compound A. 3

29
 Answer
(c) Here compound A is CH3 CH2 CHO
KMnO4
CH3 CH2 CHO + [O] → CH3 CH2 COOH
H2 SO4
CH3 CH2 COOH + R − OH → CH3 CH2 COOR + H2 O
ester

15. The following reaction is called Williamson reaction. [BB’19]

(i) 𝐑𝐎𝐇 + 𝐍𝐚 → 𝐑𝐎𝐍𝐚 + 𝐇𝟐
(𝐀)
𝐑𝐎𝐍𝐚 + 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐥 → 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐎𝐂𝐇𝟐 𝐂𝐇𝟑 + 𝐍𝐚𝐂𝐥
(𝐁) (𝐂)
(ii) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐥 + 𝐊𝐎𝐇(𝐚𝐪) → 𝐃 + 𝐊𝐂𝐥.
(c) How can you differentiate between A & C? Write with equations. 3
(d) Write down the mechanism of production of D. 4
Answer
(c) A & C are respectively alcohol and ether.
Ether is chemically less reactive than alcohol. Due to this, ether does not react with Na metal. However,
alcohol reacts with Na metal and forms H2 gas bubbles.
1
R − OH + Na → R − ONa + 2 H2 (as bubbles)
R − O − R + Na → no reaction
Alcohol and ether can be distinguished by the bubbles of H2 gas bubbles.
R − OH + PCl5 → R − Cl + POCl3 + HCl
HCl + NH3 → NH4 Cl
But, R − O − R + PCl5 → 2RCl + POCl3
As a result, HCl is not produced with which they can be distinguished.
(d) Mechanism of preparing D is similar to the (c) of board question no. 07, T-03.
16. (i) (𝐂𝐇𝟑 )𝟑 𝐂𝐗 + 𝐝𝐢𝐥𝐮𝐭𝐞 𝐛𝐚𝐬𝐞 (𝐚𝐪) →‘𝐀’ [All B’18]
(ii) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐗 + 𝐬𝐭𝐫𝐨𝐧𝐠 𝐛𝐚𝐬𝐞 (𝐚𝐪) →‘𝐁’
(c) Write the tests for differentiating ‘𝐀’ & ‘𝐁’ with reactions. 3
Answer
(c) Tests for differentiating ′A′ & ′B′ with reactions is similar to the (c) of board question no: 07, T-04.

T-05: Aldehyde and Ketone

𝐂𝐧 𝐇𝟐𝐧 𝐎𝟑 𝐇𝟐 𝐎
01. → Intermediate compound → 𝐀+𝐁 [DB’23]
𝐧 = 𝟑 𝐂𝐂𝐥𝟒 𝐙𝐧 𝐀−𝐨𝐧𝐞 𝐜𝐚𝐫𝐛𝐨𝐧
𝐜𝐚𝐫𝐛𝐨𝐧𝐲𝐥 𝐜𝐨𝐦𝐩𝐨𝐮𝐧𝐝
(c) Write the identification test of compound A with equations. 3
(d) Which of the compound between A and B shows haloform reaction? Analyze. 4
Answer
(c) Completing the reaction of the stem,

30
 Therefore, compound A is HCHO and compound B is CH3 CHO. HCHO can easily be identified by Tollen’s
reagent and Fehling solution test.
Identification by Tollens reagent: Tollen reagent produces silver mirror by reacting with aldehyde.
Aldehyde can easily be identified by this.
50°−60°C
H − CHO + [Ag(NH3 )2 ]OH → 2Ag ↓ +COONH4 + NH3 + H2 O
HCHO can be identified by above silver mirror.
Identification by Fehling solution: HCHO produces red ppt. of by reacting with Cu2 O Fehling solution.
HCHO can be identified from this red precipitation.
H − CHO + Cu(OH)2 + NaOH → HCOONa + Cu2 O ↓ +H2 O
Reddish

(d) From c, compound A is HCHO and compound B is CH3 CHO. Between HCHO and CH3 CHO, only
O
∥
CH3 CHO shows haloform reaction. The compounds having carbonyl radical (CH3 − C −) shows haloform

O
∥
reaction. This radical is absent in HCHO but present in (CH3 − C − H) . So, CH3 − CHO gives haloform

reaction.
5°C
HCHO + 3I2 + NaOH → No reaction
5°
CH3 CHO + 3I2 + NaOH → CHI3 + HCOONa + NaI + H2 O
Iodoform
Therefore, due to presence of carbonyl radical, (CH3 − CHO) i.e., compound B shows haloform reaction.
02. [RB’23]

𝐀 = 𝐂𝟒 𝐇𝟗 𝐗
𝐌 = 𝟑 carbon containing carbonyl compound which doesn’t reduce Tollen's reagent.
(d) Which one between M and N is more reactive to nucleophilic addition reaction? Explain with
reasons. 4
Answer
(d)

Reactivity of propanone and formaldehyde i,e., reactivity of aldehyde and ketone towards nucleophilic
addition reaction depends on carbonyl radical . If the positive charge decreases in that carbonyl
carbon, then reactivity decreases. Due to presence of positive inductivity in methyl or alkyl radical, they
have the capability of donating electron. So, the more methyl radical (−CH3 ) is connected to the carbonyl
compound, the more the reactivity decreases. That means, order of reactivity: HCHO > CH3 − CO − CH3 .
31
 𝟐% 𝐇𝐠𝟐+ 𝐑𝐞𝐚𝐫𝐫𝐚𝐧𝐠𝐞𝐦𝐞𝐧𝐭
03. 𝐂𝐇𝟑 − 𝐂 ≡ 𝐂𝐇 + 𝐇𝟐 𝐎 → 𝐓→ 𝐗 [SB’23]
𝟐𝟎% 𝐇𝟐 𝐒𝐎𝟒
∆
(𝐇𝐂𝐎𝐎)𝟐 𝐂𝐚 → 𝐘 + 𝐂𝐚𝐂𝐎𝟑
(d) Which of the compound between X and Y shows Cannizaro reaction? Analyze with logic. 4
Answer
O
||
(d) From c, we get, X → CH3 − C − CH3
Completing the 2nd reaction, we get:
∆
(HCOO)2 Ca → H − CHO + CaCO3
(Y)
Aldehydes without hydrogen at the α-carbon atom are simultaneously oxidized and reduced in concentrated
NaOH or KOH solution to form acids and alcohols respectively. This reaction is called Cannizzaro reaction.
Methanol gives the Cannizzaro reaction because the α-carbon atom of methanol has no hydrogen. Hence
methanoic acid and methanol are produced from methanol.
= O + NaOH → H − COONa + CH3 OH
Compound A of the stem is ethanal, CH3 CHO. α -carbon of ethanal has hydrogen. So, the compound A
doesn’t show Cannizaro reaction.
𝐊𝐎𝐇(𝐚𝐪) [𝐎] [𝐎]
04. 𝐘→ 𝐙→ 𝐌→ 𝐓 [SB’23]
𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 & 𝐇𝟐 𝐒𝐎𝟒 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 & 𝐇𝟐 𝐒𝐎𝟒
𝐓 = Monocarboxylic acid with 3 carbons.
(d) One of the compounds between M and T gives nucleophilic addition reaction and the other gives
substitution reaction. Analyze. 4
Answer
(d) From c, we get,
M compound is CH3 CH2 CHO and T compound is CH3 CH2 COOH
Though CH3 CH2 CHO i.e., propanal takes part in nucleophilic addition reaction, CH3 CH2 COOH i.e.
propanoic acid doesn’t. Because, positive charge is created in the carbonyl radical (> CO) of CH3 CH2 CHO.
Therefore, the more the positive charge increases in the carbon atom, the more the reactivity of nucleophilic
addition reaction decreases.
C=O C+ O
It mainly occurs due to the high electronegativity of oxygen atom.
On the other hand, in CH3 CH2 COOH radical, electron configuration might have variations keeping the
positions of atoms same. The reason of this resonance is O-H radical. The method of the resonance is shown
below:

It is seen that, though there is radical, C cannot uphold the positive characteristics. And the first

condition for nucleophilic addition reaction is the polarization of Carbon and Oxygen in which cannot

32
 occur in −COOH radical. So, it can be said that between M and T, M i.e., CH3 CH2 CHO is reactive to
nucleophilic addition reaction but T i.e. CH3 CH2 COOH is not reactive toward nucleophilic addition reaction.
On the other hand, though propanal doesn’t show substitution reaction but propanoic acid can replace H or
OH. For example:
1
H substitution: CH2 CH2 COOH + Mg → (CH3 CH2 COO)2 Mg + 2 H2
1
CH3 CH2 COOH + Na → CH3 CH2 COONa + 2 H2
OH substitution: CH3 CH2 COOH + PCl5 → CH3 CH2 COCl + POCl3 + HCl
𝐢. 𝐎𝐳𝐨𝐧𝐨𝐥𝐲𝐬𝐢𝐬
05. 2-methyl propene 𝐢𝐢. 𝐙𝐧/𝐇𝟐 𝐎
𝐀 + 𝐁 + 𝐙𝐧𝐎 + 𝐇𝟐 𝐎 [BB’23]
Compound A doesn’t give haloform reaction.
(d) Analyze the order of reactivity of compound A and B in addition reaction. 4
Answer
(d) Chemical reactivity of methanal (A) and propanone (B): The reactivity of aldehydes and ketones in

nucleophilic addition reaction depends on the amount of positive charge on the carbonyl carbon . If the
level of positive charge (δ+) on the carbonyl carbon decreases for any reason, the activity of the compound also
decreases. Alkyl radicals such as methyl radical (−CH3 ) and ethyl radical (CH3 CH2 −) have the ability of
donating positive inductivity or electron density.
So, the more the −CH3 radical and CH3 − CH2− radical attached with the carbonyl compound, the more the
positive charge decreases. In this case, between methanal and propanone, methanal (A) is more reactive than that
of propanone (B). Therefore, the order of reactivity is: A > B.

𝐍𝐢⁄𝐏𝐭 (𝐢) 𝐎𝟑
06. 𝐀 (𝐂𝐧 𝐇𝟐𝐧−𝟐 ) → 𝐁→ 𝐂+𝐃 [CB’23]
(𝐧=𝟑) 𝐇𝟐 ,𝟐𝟎𝟎°𝐂 (𝐢𝐢)𝐙𝐧/𝐇𝟐 𝐎
(𝐂 𝐚𝐧𝐝 𝐃 𝐚𝐫𝐞 𝟏 𝐚𝐧𝐝 𝟐 𝐜𝐚𝐫𝐛𝐨𝐧 𝐜𝐨𝐦𝐩𝐨𝐮𝐧𝐝 𝐫𝐞𝐬𝐩𝐞𝐜𝐭𝐢𝐯𝐞𝐥𝐲)

(d) Between C and D of the stem “one shows aldol condensation, the other shows cannizaro reaction”-
explain the statement with logic and reactions. 4
Answer
(d)

Here, B is nitrobenzene and C is aniline. −NH2 is a benzene ring activating group. Its resonance is as follows -

I II III IV V
−NH2 radical pushes its lone pair cloud into the benzene ring by positive mesomeric effect. Then according
to II-IV the benzene ring is activated by increasing the electron density in the ortho-para position. On the
other hand, −NO2 is a benzene ring deactivating group. Its resonance is as follows-

33
 (I) (II) (III) (IV) (V)
The −NO2 radical pulls the electron cloud of the benzene ring towards itself by the negative mesomeric
effect. As a result, the electron density in the ortho-para position is reduced according to resonance structure
II-IV; As a result, the benzene ring is deactivated. That is why it is more inactive than benzene.
∴ Order of reactivity will be B < C.
07. [Din.B’23]

(d) Between B and C compound, one gives both aldol condensation reaction and haloform reaction,
but the other doesn’t – analyze. 4
Answer
(d) Completing the reaction in the stem, we get,

Between B and C compound, B gives both aldol condensation and haloform reaction but C doesn’t.
Only carbonyl compound with α − H shows aldol condensation reaction. Aldol condensation reaction at first
produce carbanion from one molecule of CH3 − CHO during the reaction in presence of dilute NaOH and
alpha (α) H-atom containing carbonyl compound. Later, this carbanion converts into negative ion by
combining with the partially positive carbonyl carbon of the 2nd CH3 − CHO by nucleophilic addition
reaction. At last, that negative ion completes the reaction by accepting proton from H2 O. As the produced
compound has both aldehyde (−CHO) and alcohol (−OH) radical, such reaction is called aldol condensation
reaction. (Ald + ol = Aldol). Reaction of eliminating water from aldol is called aldol condensation reaction.

OH
|
CH3 − C − CH2 − CHO → H2 O + CH3 − CH = CH − CHO
|
H 3−hydroxy butanal or aldol
O
∥
Again, for haloform reaction, there must be CH3 − C − radical. Though B has the radical, it is absent in C.
So, C doesn’t give haloform reaction but B gives. That means,
CH3 CHO (B) + 3I2 + 4NaOH → CHI3 ↓ + HCOONa + 3NaI + H2 O
Iodoform

34
08. [MB’23]

(c) Write the identification test of functional group in compound Q of the stem with equations. 3
Answer
(c)

Identification of Butanon: 2: 4 − DNPH test.

2, 4 DNPH Butanon -2, 4 – dinitro

phenyl hydrazone

09. [DB’22]

(c) Write the identification test for the functional group of the Q compound of the stem along
with the equation. 3
Answer
(c) Q compound of the stem is a carbonyl compound similar to the (c) of board question no. 08, T-05.

10. Consider the stem and answer the following questions: [Ctg.B’22]
𝐙𝐧−𝐇𝐠
(i) ‘𝐗’ 𝐂𝐇𝟑 − 𝐂𝐇𝟑 + 𝐇𝟐 𝐎
𝐜𝐨𝐧𝐜𝐞𝐧𝐭𝐫𝐚𝐭𝐞𝐝 𝐇𝐂𝐈
𝐙𝐧−𝐇𝐠
(ii) ‘𝐘’ 𝐜𝐨𝐧𝐜𝐞𝐧𝐭𝐫𝐚𝐭𝐞𝐝 𝐇𝐂𝐈 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟑 + 𝐇𝟐 𝐎
(d) In nucleophilic addition reaction, ‘X’ compound is more reactive than ‘Y’ compound – Explain it. 4
Answer
(d) In the Nucleophilic addition reaction X is more reactive than Y the reason is similar to the (d) of board
question no. 02, T-05.
𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 /𝐇+ 𝐝𝐢𝐥. 𝐍𝐚𝐎𝐇
11. 𝐀→ 𝐁→ 𝐂 [SB’22]
[𝐎]
Compound ‘A’ has two carbons. Compound B gives yellow precipitate while reacting with 2, 4 DNPH
and reduces Fehling’s solution.
(c) Describe the mechanism of preparing compound C from compound B. 3
(d) Which reaction between Cannizaro and Aldol condensation reaction will be showed by compound
B of the stem? Analyze with equations. 4

35
 Answer
K2 Cr2 O7 ∕H+ dil.NaOH
(c) CH3 CH2 OH → CH3 CHO →
[O]
(A) (B)

B is aldehyde and C is aldol.

Preparation of C from B compound:

(d) The compound B gives the aldol condensation between Cannizaro and aldol condensation.
Carbonyl compound containing α − H, can only show Aldol condensation reaction. Acetaldehyde
(CH3 − CHO) containing α − H reacts to produce carbanion in presence of dilute NaOH. The carbanion
turns into negative ion by doing nucleophilic reaction with the partial 2nd CH3 − CHO positive carbonyl
carbon and getting attached with carbon-carbon bond. Lastly, the negative ion receives a proton H + ion from
water to complete the reaction. In the produced compound, due to presence of both aldehyde group (−CHO)
and alcohol group (−OH), the reaction is known as aldol condensation. (Ald + ol = Aldol)

N:B: In ketone, containing α − H for example (CH3 − CO − CH3 ) nucleophilic substitution occurs; but in
the product there remains ketone group (−CO −) and (−OH) group; in this case, the reaction is also called
aldol condensation. In this case, the reaction rate is low.
12. [BB’22]

(c) Show with the help of reactions that compounds B and C have different functional groups. 3
(d) Which is more reactive in the nucleophilic addition reaction between compounds B and C?
Analyze. 4
Answer
(c) The reaction is:

Zn
→ CH3 CHO + CH3 COCH3 + ZnO
H2 O (B) (C)

Here the functional group of compound B (aldehyde) is −CHO

On the other hand, the functional group of compound C (ketones) is −CO −.
That is, their functional groups are different.

36
(d) Similar to the (d) of board question no. 02, T-05. Answer: B ⇒ CH3 − CHO, C ⇒ CH3 − CO − CH3 .
Thus, the order of their reactivity: CH3 − CHO > CH3 − CO − CH3
[𝐎] [𝐎]
13. 𝐂𝟑 𝐇𝟖 𝐎 → 𝐀 → 𝐁 [JB’22]
(𝐗)
[𝐎]
𝐂𝟑 𝐇𝟖 𝐎 → 𝐂
(𝐘) 𝐏𝐚𝐫𝐭𝐢𝐚𝐥 𝐎𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧

[X and Y are 𝟏° and 𝟐° alcohol respectively.]

(d) Which one between A and C is more reactive in nucleophilic addition reaction? Analyze. 4
Answer
(d) Similar to the (d) of board question no. 02, T-05. Answer: A = CH3 CH2 CHO, C = CH3 COCH3
14. Notice the following stem and answer the given questions: [CB’22]

‘R’ is alkyl group with two carbons.

(c) How ‘D’ and ‘B’ can be differentiated? Write with equations. 3
(d) Which reaction will give compound ‘D’ show aldol condensation or Cannizaro reaction? Analyze. 4
Answer
(c) The reactions are:
mild KOH(aq) KCN(alc) H+
CH3 CHO ← CH3 − CH2 − OH ← CH3 CH2 − I → CH3 CH2 − CN → CH3 CH2 COOH
oxidation H2 O
D C A B
B is propanoic acid and D is ethanal. By reaction of PCl5 with B and D, B (propanoic acid) produces HCl acid
and D(ethanal) does not.
CH3 Cl + 2COOH + PCl5 → CH3 CH2 COCl + POCl3 + HCl
(B)
CH3 CHO + PCl5 → CH3 CHCl2 + POCl3
(D)

(d) Compound ‘D’ of the stem is aldehyde which shows aldol condensation reaction. The remaining part is similar
to the (d) of board question no. 11, T-05.
15. [Din.B’22]

(i)

(ii)

(d) Which one between compound ‘P’ and ‘Q’ shows nucleophilic addition reaction? Analyze. 4
Answer
[O] [O]
(d) R − CH2 − OH → CH3 − CHO → CH3 − COOH
K2 Cr2 O7 +H2 SO4 (P) K2 Cr2 O7 +H2 SO4 (Q)

P is a carbonyl compound so P will take part in nucleophilic addition reaction.

37
 Nucleophilic addition reaction:
Aldehyde-ketone having divalent carbonyl group , gives nucleophilic addition reaction. Electronegativity
difference between oxygen and carbon atom is high (3.5 − 2.5 = 1.0) so pi-bonded (π) electron of
group is attracted more to oxygen atom. Thus, partial negative (δ− ) and positive charge (δ+ ) is formed in oxygen
and carbon atom respectively. In this way, positive atom of polarized carbonyl group is attacked by negative
center-attracting reagent or nucleophile and thus nucleophilic addition occurs . Here, cyanide ion (CN− )
(from HCN) as nucleophile, sodium sulfite ion ( −OSO2 Na) (from NaHSO3 ), molecule, Grignard reagent
acts as carbanion.
Nucleophilic addition reaction mechanism:
Ionization of H − CN increases in presence of dilute NaOH base. The produced high number cyanide ion
attacks partially positive charged carbonyl carbon as nucleophile. At the last step, when negative oxygen atom
receives proton (H+ ) from water molecule (H2 O) then addition reaction ends.

[𝐎] [𝐎]
16. (i) Compound A → compound B → 𝐜𝐨𝐦𝐩𝐨𝐮𝐧𝐝 C [MB’22]
𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 +𝐇𝟐 𝐒𝐎𝟒 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 +𝐇𝟐 𝐒𝐎𝟒
𝐍𝐚𝐎𝐇+𝐂𝐚𝐎
(ii) Compound C → 𝐂𝐇𝟒 + 𝐍𝐚𝟐 𝐂𝐎𝟑 (𝐂𝐚𝐎)
∆
(c) Explain which of compounds B and C will exhibit nucleophilic addition reaction. 3
(d) How do you identify the functional groups of compounds B and C? Write with equations. 4
Answer
(c) Compound C is CH3 COOH. Because it produces CH4 by decarboxylation reaction.
If compound C is CH3 COOH , then B is CH3 CHO.
Remaining part is similar to the (d) of board question no. 04, T-05.
(d) The functional groups of compounds B and C are −CHO and −COOH respectively i.e., aldehyde and carboxylic
groups respectively.
Below is the solution identification test for CH3 − COOH and CH3 − CHO:
Test with 𝐍𝐚𝐇𝐂𝐎𝟑:
Reaction of CH3 − COOH with 5% NaHCO3 solution produces CO2 gas with bubbles and CH3 COONa and water.
This is the identifying test for the carboxyl radical.
CH3 COOH(aq) + NaHCO3 (aq) → CH3 COONa (aq) + CO2 (g) + H2 O(l)
Tollen’s Reagent Test:
If CH3 − CHO reacts with Tollen's reagent (ammonia solution mixed with 10% silver nitrate containing
[ Ag(NH3)2 ] OH; a white precipitate of silver is formed.
Δ
CH3 − CHO + 2[Ag (NH3 )2 ] OH → 2Ag ↓ +CH3 COONH4 + 3NH3 + H2 O
50°C like mirror(white)
Fehling solution Test:
5-6 drops of organic compound in the test tube and add 2-3 mL of Fehling’s solution and heat the test tube in hot
water for 2-3 minutes. Formation of a reddish precipitate (Cu2 O ) confirms the presence of aldehyde. Ketone does
not give this test.
+ Δ +
CH3 CHO(l) + 2Cu(OH)2 (aq) + NaOH− → CH3 COO− Na (aq) + Cu2 O (s) + H2 O (l)
sodium ethanoate reddish

38
17. [DB’21]

P doesn’t react with Tollen’s reagent but Q does.

(d) Differentiate between P and Q compound with reaction. 4
Answer
(d) Completing the reaction we get,

As P and Q are two different compounds A will be-

P doesn’t react with Tollens reagent. So, P is propanone. Q is methanal.

Propanone does not react with weak oxidant Tollen’s reagent and But methanal reacts to form silver mirror.
Tollen’s reagent test:

+2[Ag (NH3 )OH] → No reaction

∆
HCHO + 2[Ag(NH3 )2]OH(aq) → 2 Ag(s) + H − COONH4 + 3NH3 + H2 O
50°C
Again, propanone does not react with Fehling’s reagent but methanal gives red precipitate with Fehling’s reagent.
Fehling’s solution test:
∆
+Cu(OH)2 + NaOH → No reaction
50°C
HCHO + Cu(OH)2 + NaOH → HCOONa(aq) + Cu2O(s) + H2 O(l)
Red
There are differences between P and Q.
18. Answer the following questions according to the stem: [RB’21]
𝐂𝐇𝟑
|
(i) 𝐂𝐇𝟑 − 𝐂 − 𝐂𝐥 + 𝐍𝐚𝐎𝐇(𝐚𝐪) → 𝐏 + 𝐍𝐚𝐂𝐥
|
𝐂𝐇𝟑

𝐂𝐂𝐥𝟒
(ii) +𝐎𝟑 → 𝐀+𝐁
𝐙𝐧,𝐇𝟐 𝐎

(d) Which of the compounds A and B shows haloform reaction? Explain with reaction. 4
Answer

(d)

A shows haloform reaction between A and B.

O
||
The haloform reaction is exhibited by only compounds containing methyl carbonyl (CH3 − C −).

39
 O
||
Since CH3 − CO − CH3 has (CH3 − C −) group, it gives the haloform reaction. On the other hand,

O
∥
CH3 − CH2 − CHO compound does not have (CH3 − C −) group, it will not give haloform reaction.

Reaction:
O
|| 5°C
CH3 C − CH3 + 3I2 + 4NaOH → CHI3 + HCOONa + 3NaI + 3H2 O.
19. [CB’21]
𝐍𝐚𝐎𝐇/𝐂𝐚𝐎 𝐂𝐇𝟑 𝐂𝐥
COONa → 𝐗→ 𝐘
△ 𝐚𝐧𝐡𝐲𝐝𝐫𝐨𝐮𝐬 𝐀𝐥𝐂𝐥𝟑
𝐝𝐫𝐲 𝐞𝐭𝐡𝐞𝐫
𝟐𝐂𝐇𝟑 𝐂𝐥 + 𝟐𝐍𝐚 → 𝐙 + 𝟐𝐍𝐚𝐂𝐥
(c) How will Z be formed from the carbonyl compound? 3
Answer
(c) Reaction in the stem is,
Dry ether
2CH3 Cl + 2Na → CH3 − CH3 +2NaCl
ethane (Z)
∴ Z is ethane. Ethane is prepared below from the carbonyl compound.
O
∥ Zn−Hg
∴ CH3 − C − H + [H] → CH3 − CH3 + H2 O
conc.HCl ethane

20. [BB’21]

(c) Which of the compounds B and C of the stem gives aldol condensation reaction? Analyze. 3
(d) One of the compounds of B and D is active in nucleophilic addition reaction while the other is not
– analyze with reason. 4
Answer
(c) Since A = Cn H2n and n = 3, A is C3 H6
This is the reaction we get from 1st part,
O3 /CCl4
C3 H6 → CH3 − CHO + H − CHO
Zn/H2 O
(A) (B) (C)
Here, B is CH3 − CHO and C is H − CHO and B molecule i.e., CH3 − CHO gives aldol condensation reaction.
The reason is described below: The only condition for the aldol condensation reaction is the presence of at least
one hydrogen atom on the α-carbon atom. That is, aldehydes or ketones that do not contain α-hydrogen do not
give aldol reactions. Compounds B has α-hydrogens. But C (H-CHO) does not contain α-hydrogen. Hence
compound B ie. CH3− CHO gives aldol condensation reaction.
O
∥ Dilute
CH3 − C − H + H3 C − CHO →
NaOH

(d) Similar to the (d) of board question no. 04, T-05. B = CH3 CHO, D = CH3 COOH

40
21. [MB’21]

Both A and B contains carbonyl group.

(d) Between A and B which one is more reactive in nucleophilic addition? Discuss. 4
Answer
(d) Similar to the (d) of board question no. 02, T-05. A = CH3 CH2 CHO, B = CH3 − CO − CH3 and A > B.
(𝐢)𝐎𝟑 𝐊𝐎𝐇 (𝐚𝐥𝐜) 𝐊𝐎𝐇 (𝐚𝐪) 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕
22. 𝟐 ‘𝐁’ ← ‘𝐀’ ← ‘𝐗’ → ‘Y’ → ‘Z’
(𝐢𝐢)𝐙𝐧/𝐇𝟐 𝐎 +𝐇𝟐 𝐒𝐎𝟒

‘𝐗’= An isomer of 𝐂𝟒 𝐇𝟗 Br; ‘Z’ or ‘𝐁’ + 𝟐,

4-DNPH→ Yellow precipitate [DB’19]
‘𝐁’+ Tollen’s reagent →Ag mirror
(d) Will the reactivity of Nucleophilic addition reactions for the compounds ‘𝐁’ and ‘𝐙’ be the same?
Analyze. 4
Answer
(d) Reactivity of ‘B’ and ‘Z’ towards nucleophilic addition reaction is different. Analysis of its reason is similar to
the (d) of board question no. 02, T-05.
[𝐎] 𝐙𝐧.𝐇𝐠
23. 𝐀← 𝐇𝐂𝐇𝐎 → 𝐁 + 𝐇𝟐 𝐎 [DB’19]
𝐜𝐨𝐧𝐜 𝐇𝐂𝐥
(d) Can the compound `𝐀′ in the stem give the Silver mirror test? Analyze. 4
Answer
(d) HCHO + [O] → HCOOH
A
methanoic Acid
O
||
The structural formula of methanoic acid is H − C − OH; from which it is seen that the functional groups for both
carboxylic acid and aldehyde is present.
O O
|| ||
H − C − OH Carboxyl group (C − OH) Aldehyde group (−C − H)
||
O
Also, due to the presence of two different functional groups, it shows the characteristics of both acid and aldehyde,
and aldehydes generally give the silver mirror test. Primarily, the aldehyde group reacts with Tollens reagent and
produce silver mirror. Since methanoic acid contains aldehyde group, it can reduce Tollens reagent. The reaction
is shown below:
H − COOH + [Ag(NH3 )2 ]OH → Ag ↓ + (NH4 )2 (CO3 ) + NH3 + H2 O
silver mirror
Again, Methanoic acid simultaneously acts as an acid.
HCOOH + Na2 CO3 → HCOONa + H2 O + CO2
Therefore, since, methanoic acid possesses carboxylic acid and aldehyde functional groups, it gives silver mirror test.

41
 𝐏𝐝, 𝐁𝐚𝐒𝐎𝟒 𝐎𝟑
24. 𝐀→ 𝐁→ 𝐂 + 𝐃 + 𝐙𝐧𝐎 ; ‘A’ is three carbon alkyne. [RB’19]
𝐇𝟐 𝐙𝐧

(d) Show with reaction if C and D will show haloform reaction or not- Analyze. 4
Answer
(d) Analysis of which of the compound between C and D will show haloform reaction the reason is similar to the
(d) of board question no 18, T-05.

25. [Ctg.B’19]
isomer i. O3
A C+D
C4H8 ii. H2O/Zn
isomer i. O
B 3 2E
ii. H2O/Zn
[‘C’ does not create precipitate with tollen’s reagent]
(d) Describe the order of reactivity of nucleophilic addition reaction of ‘C’, ‘D’ and ‘E’. 4
Answer
(d) Similar to the (d) of board question no. 02, T-05,
HCHO > CH3 CHO > CH3 − COCH3
(D) (E) (C)
(Reactivity CH3 CHO of decreases than that of HCHO due to the presence of CH3 group)

𝐏𝐂𝐥𝟓 𝐏𝐝
26. 𝐂𝐇𝟑 − 𝐂𝐎𝐎𝐇 → ′𝐗′ → ′𝐀′ + 𝐇𝐂𝐥 [SB’19]
𝐁𝐚𝐒𝐎𝟒
𝐏𝐂𝐥𝟓 𝐏𝐝
𝐂𝐎𝐎𝐇 → ′𝐘 ′ → ′𝐁′ + 𝐇𝐂𝐥
𝐁𝐚𝐒𝐎𝟒

(d) Which one between A and B gives aldol condensation reaction? Analyze. 4
Answer
PCl5 Pd(H2 )
(d) CH3 − COOH → CH3 COCl → CH3 CHO + HCl
BaSO4 (A)
PCl5 Pd,( H2 )
COOH → COCl → CHO + HCl
BaSO4 (B)

Between A and B, A, that is, ethanal gives aldol condensation reaction.

The aldehydes or ketones which have α hydrogen, they react among themselves in presence of dilute acid or base.
In CH3 CHO, there are 3 H in the α − C. So, it produces 3-hydroxybutanal or aldol in NaOH solution.
α−C
NaOH
2CH3 CHO → CH3 − CH(OH) − CH2 CHO
aldol

But in CHO, there is no H atom in α − C. So, it produces one mole of alcohol and one mole of acid in
NaOH solution.
NaOH
2 CHO → COONa + CH2 OH

Thus, CHO does not give aldol condensation reaction but CH3 CHO does.

42
 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 +𝐇𝟐 𝐒𝐎𝟒 (𝐂𝐨𝐧𝐜.)
27. (i) C𝐇𝟑 –C𝐇𝟐 –OH → ′𝐏 ′ + 𝐇𝟐 𝐎 [SB’19]
𝐩𝐚𝐫𝐭𝐢𝐚𝐥 𝐨𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 +𝐇𝟐 𝐒𝐎𝟒 (𝐂𝐨𝐧𝐜.)
(ii) C𝐇𝟑 –𝐂𝐇–C𝐇𝟑 → ′𝐐′ + 𝐇𝟐 𝐎
| 𝐩𝐚𝐫𝐭𝐢𝐚𝐥 𝐨𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
𝐎𝐇

(iii) 𝐂𝐇𝟑 –C𝐇𝟐 –OH+𝐇𝟐 S𝐎𝟒 (excess)

′𝐐′+𝐇𝟐 𝐎
→ ′R′ + [𝐇𝟐 𝐒𝐎𝟒 + 𝐇𝟐 𝐎]
∆
(c) How will you convert compound ‘P’ into C𝐇𝟒 ? Write with equations. 3
(d) Which one between ‘Q’ and ‘R’ gives nucleophilic addition reaction? Analyze. 4
Answer
K2 Cr2 O7 +H2 SO4
(c) CH3 CH2 OH → CH3 CHO + H2 O
partial oxidation (P)

P is ethanal. Oxidizing ethanal, ethanoic acid; then reacting with NaOH, Na ethanoate and finally reacting with
soda lime, CH4 is prepared.
K2 Cr2 O7
CH3 CHO + [O] → CH3 COOH
H2 SO4

CH3 COOH + NaOH → CH3 COONa + H2 O

NaOH(CaO)
CH3 COONa → CH4 + Na2 CO3
∆
(d) The two reactions in the stem are-
K2 Cr2 O7 +H2 SO4
(i) CH3 CH − CH3 → CH3 − C − CH3
| partial oxidation ||
OH O
(Q)

(ii) CH3 CH2 OH + H2 SO4 → CH2 = CH2

(R)

Q and R are propanone and ethene respectively. Among them, propanone gives nucleophilic addition reaction.
In propanone, more highly electronegative oxygen atoms are bonded with carbon through pi (π) bond. And in
ethene, the pi (π) bond exists between two carbon atoms.
Due to polarity carbon oxygen double bond, carbon gets partially positively charged.
O Oδ−
|| |
CH3 − C − CH3 → CH3 − C δ+ − CH3
As a result, nucleophile attracts carbocation, and so CH3 COCH3 gives nucleophilic addition reaction.
But the pi (π) bond of ethene is attracted by electrophilic, so ethene gives electrophilic addition reaction.
Therefore, between Q and R, Q gives nucleophilic addition reaction.

28. [JB’19]
𝐑𝐌𝐠𝐗 𝐙𝐧𝐂𝐥𝟐 +𝐇𝐂𝐥
𝐂𝐂𝐥𝟒 𝐙𝐧,𝐇𝟐 𝐎
C → 𝐄→ 𝐰𝐡𝐢𝐭𝐞 𝐩𝐫𝐞𝐜𝐢𝐩𝐢𝐭𝐚𝐭𝐞 (𝐟𝐚𝐬𝐭)
𝐇 +/𝐇𝟐 𝐎
𝐀 + 𝐎𝟑 → 𝐁→ 𝐑𝐌𝐠𝐗 𝐙𝐧𝐂𝐥𝟐 +𝐇𝐂𝐥
D 𝐇→+/𝐇𝟐𝐎 𝐅 → 𝐰𝐡𝐢𝐭𝐞 𝐩𝐫𝐞𝐜𝐢𝐩𝐢𝐭𝐚𝐭𝐞 (𝐀𝐟𝐭𝐞𝐫 𝟓 − 𝟏𝟎 𝐦𝐢𝐧)

(d) Among C and D which one is more reactive to nucleophilic addition reaction? Discuss with logic. 4
Answer
(d) Similar to the (d) of board question no. 02, T-05. Answer: order of reactivity: CH3 CHO > CH3 COCH3

43
 𝟐%𝐇𝐠𝐒𝐎𝟒 𝐫𝐞𝐚𝐫𝐫𝐚𝐧𝐠𝐞𝐦𝐞𝐧𝐭
29. (i) 𝐂𝐇𝟑 − 𝐂 ≡ 𝐂𝐇 + 𝐇𝟐 𝐎 → 𝐏 → 𝐁 [CB’19]
𝟐𝟎%𝐇𝟐 𝐒𝐎𝟒,𝟔𝟎°𝐂 𝐮𝐧𝐬𝐭𝐚𝐛𝐥𝐞
𝟐%𝐇𝐠𝐒𝐎𝟒 𝐫𝐞𝐚𝐫𝐫𝐚𝐧𝐠𝐞𝐦𝐞𝐧𝐭
(ii) 𝐂𝐧 𝐇𝟐𝐧−𝟐 +𝐇𝟐 𝐎 → 𝐍 → A
𝟐𝟎%𝐇𝟐 𝐒𝐎𝟒 ,𝟔𝟎°𝐂 𝐮𝐧𝐬𝐭𝐚𝐛𝐥𝐞
𝐅𝐞
(iii) 𝟑𝐂𝐧 𝐇𝟐𝐧−𝟐 → M [here n=2]
𝟒𝟓𝟎°𝐂
(d) Which one among A & B is more active towards nucleophilic reagent? Explain. 4
Answer
(d) According to stem, compound A is methanal and compound B is propanone. Remaining part similar to the (d)
of board question no. 02, T-05.
30. [Din.B’19]
𝐑𝐞𝐝𝐮𝐜𝐭𝐢𝐨𝐧 (𝐰𝐞𝐚𝐤) 𝐚𝐪.𝐊𝐎𝐇 𝐚𝐥𝐜.𝐊𝐂𝐍 𝐇𝟐 𝐎
𝐃 ← 𝐂 ← 𝐑−𝐈 → 𝐀→ 𝐁
𝐇+
‘R’ is an alkyl group having two carbons.
(d) Will the compound D show aldol condensation or Cannizzaro reaction? Analyze. 4
Answer
(d) Compound D will show aldol condensation reaction. Analysis of its reason is similar to the (d) of board question
no: 11, T-05.
31. [All B’18]
isomer i. O3
A ‘X’ + ‘Y’
ii. Zn/H 2O
C 4H8 isomer i. O3
B 2 ‘M’
ii. Zn/H 2O
['X' forms white precipitate with Tollen’s reagent but 'Y' doesn’t react with it]
(c) 'X' is more reactive than 'M' in nucleophilic substitution reaction – Explain. 3
Answer
(c) ‘M’ is less reactive than ‘X’ is nucleophilic addition reaction- explanation is similar to the (d) of board question
no. 02, T-05.

T-06: Carboxylic acid, acid halide, Amide, Amine, Anhydride and Ester

[𝐎] [𝐎]
01. 𝐂𝟑 𝐇𝟖 𝐎 → 𝐀 → 𝐁 [JB’22]
(𝐗)
[𝐎]
𝐂𝟑 𝐇𝟖 𝐎 → 𝐂
(𝐘) 𝐏𝐚𝐫𝐭𝐢𝐚𝐥 𝐎𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧

[X and Y are 𝟏° and 𝟐° alcohol respectively.]

(c) Write down the identification reaction of compound B with reactions. 3
Answer
(c)
[O] [O]
C3 H8 O → C3 H6 O → C2 H5 COOH
(X) (A) (B)
1° Alcohol
Compound B is propanoic acid.

44
 Identification:
1. Litmus test:
+H2 O
CH3 − CH2 − COOH ⇌ CH3 − CH2 − COO− + H3 O+
H3 O+ + Blue litmus→ Red litmus
2. 𝐍𝐚𝐇𝐂𝐎𝟑 solution test: CO2 gas is emitted during the reaction of organic acid with 5% of this solution.
CH3 − CH2 − COOH + NaHCO3 → CH3 CH COONa + CO2 (g) + H2 O(g)
↓
With bubbles
𝐒𝐧
02. (i) 𝐑 − 𝐍𝐎𝟐 + [𝐇] → 𝐀 [SB’21]
𝐇𝐂𝐥
𝐒𝐧
(ii) 𝐀𝐫 − 𝐍𝐎𝟐 + [𝐇] → 𝐁
𝐇𝐂𝐥
(c) In the stem, which one is more basic between A and B? Explain. 3
Answer
(c) Completing the two reactions of the stem,
Sn Sn
(i) R − NO2 + [H] → R − NH2 (ii) Ar − NO2 + [H] → Ar − NH2
HCl A HCl B
Here A is 1° aliphatic amine and B is aromatic amine.
The basicity of amines depends on the density of the electron cloud on N. As CH3 is the electron-donating group,
the density of the electron cloud on N of NH3 is increased. On the other hand, as benzene ring is the electron-
receiving group, it decreases the net electron density on N of NH2 . The order of basicity of amine is: 2° > 1° >
3° > NH3 > NH2
𝐑𝐞𝐝𝐮𝐜𝐭𝐢𝐨𝐧 (𝐰𝐞𝐚𝐤) 𝐚𝐪.𝐊𝐎𝐇 𝐚𝐥𝐜.𝐊𝐂𝐍 𝐇𝟐 𝐎
03. 𝐃 ← 𝐂 ← 𝐑−𝐈 → 𝐀→ 𝐁 [Din.B’19]
𝐇+
‘R’ is an alkyl group having two carbons.
(c) Show the synthesis of B from Grignard reagent. 3
Answer
alc. KCN H2 O
(c) In the stem B is R − COOH because R − I → KI + R − CN → + R − COOH + NH3
(A) H (B)
Its synthesis from Grignard reagent is shown below:
O
H2 O ||
RMgX + O = C = O → R − C − OH + Mg(OH)X
Through this reaction, B can be produced.
04. [DB’17]
𝐅𝐞 𝐂𝐇𝟑 𝐂𝐥
𝐀 → 𝐁; 𝐁→ 𝐂 → 𝐓𝐍𝐓
𝐮𝐧𝐬𝐚𝐭𝐮𝐫𝐞𝐭𝐞𝐝 𝐜𝐨𝐦𝐩𝐨𝐮𝐧𝐝 𝟒𝟎𝟎°𝐂 𝐚𝐧𝐡𝐲𝐝𝐫𝐨𝐮𝐬 𝐀𝐥𝐂𝐥𝟑
𝐰𝐢𝐭𝐡 𝟐−𝐜𝐚𝐫𝐛𝐨𝐧
(c) How can carboxylic acid be prepared from A-write down with equations. 3
Answer
Fe
(c) From the reaction in the stem, CH ≡ CH → C6 H6
(A) 400°C
Since A is a two carbon unsaturated compound, A is ethyne or acetylene. The preparation of carboxylic acid from
ethyne is given below with reactions:
O
||
2% Hg2+
CH ≡ CH + H − OH 20% H CH3 − C −H
2 SO4 ethanal
60°C
2CH3 CHO + O2 → 2CH3 COOH
(CH3 COO)2 Mn carboxylic acid (acetic acid)

45
05. [RB’17]
2% Hg2+
B
20% H2SO4
CH3- C CH
+H2 conc. H2SO4 H2O
X Y Z
Pd-BaSO4
(c) Write down the equations and describe how carboxylic acid is prepared from ‘X’ compound. 3
Answer
(c) By completing the reaction given in stem,

Hence it is seen that X compound is alkene that means propene. Formation of carboxylic acid from propene is
shown below along with equations. In presence of catalyst H3 PO4 , propene, carbon mono-oxide, and hot vapor
mixture in high pressure is heated at 350-400°C temparature, then carboxylic acid is prepared.
CH3
H3 PO4 |
CH3 − CH = CH2 + CO + H2 O → CH3 − CH − COOH
350−400°C

T-07: Aromatic compound

01. [DB’23]

(c) Why the substituent doesn’t attach at ortho-para position in the nitration of compound C
in the stem? Explain. 3
(d) Analyze the order of reactivity in electrophilic substitution in case of compounds A, B and C of
the stem. 4
Answer
(c) Completing the reaction in the stem, we get:

Therefore, compound C is aniline. In nitration of aniline, substituent gets attached to meta position, not in ortho
para position. −NH2 group of aniline is otho-para indicator. According to conventional rule, the substituent
should attach to ortho para postion, but it doesn’t occur in reality. In nitration of aniline, mixture of concentrated
H2 SO4 and HNO3 is used. H + produced from the aqueos solution of H2 SO4 is accepted by −NH2 with its lone
+
pair electron and produce C6 H5 − NH3 which behaves like a meta indicator group. Later on, when it reacts with
nitric acid, meta-nitro aniline is produced as the major product.

46
(d)

Benzene ring activating group like, −R, −NH2 , −OH etc. increases the activity of benzene ring.
Again, benzene ring deactivating group like- −CHO, −NO2 , −CN etc. decreases the activity of benzene ring.
That means- order of reactivity in electrophilic reaction of A, B and C:

−NH2 is a benzene ring activating group. Its resonance is-

I II III IV V
−NH2 radical pushes the cloud of electron pair towards the benzene ring by mesomeric effect. Then, according
to II-IV, benzene ring becomes activate because of increase in electron density at ortho para position. On the
other hand, −NO2 is a benzene ring deactivating group. Its resonance is as follows:

(I) (II) (III) (IV) (V)

−NO2 radical attracts the electron cloud of benzene ring by mesomeric effect. Then, according to II-IV, benzene
ring becomes deactivate because of decrease in electron density at ortho para position. As a result, it becomes
more inactive than that of benzene.
𝐇𝟐
02. 𝐂𝐚𝐂𝟐 + 𝐇𝟐 𝐎 → 𝐀→ 𝐁 [DB’23]
𝐏𝐝−𝐁𝐚𝐒𝐎𝟒
(c) Why unsaturation of the compound produced in the polymerization of A in the stem is not similar
to that of B? Explain. 3
Answer
(c) Completing the reaction in stem we get,
H2
CaC2 + H2 O → CH ≡ CH → CH2 = CH2
A Pd−BaSO4 B
A is ethyne (CH ≡ CH) and B is ethene (CH2 = CH2 )
Polymerization of A,
Fe
CH ≡ CH →
A 450°C
Benzene
Unsaturation of benzene is not like that of ethene. Carbon carbon pi electron in the double bonds of benzene is
resonating but pi electrons present in ethene are not resonating. Moreover, benzene doesn’t show unsaturation
test and Bayer test like ethene.
47
 Bromine solution test:

red colorless

Bayer’s test:

pink colorless

Therefore, benzene is a special type of unsaturated compound which is not like ethene.
03. [RB’23]
𝐂𝐚𝐎 𝐂𝐇𝟑 𝐂𝐥 [𝐎]
→ 𝐀→ 𝐁→ 𝐂
∆ 𝐝𝐫𝐲 𝐀𝐥𝐂𝐥𝟑 𝐝𝐢𝐥𝐮𝐭𝐞 𝐇𝐍𝐎𝟑
(c) Describe the reaction of compound B with chlorine in boiling state with equations. 3
(d) Write the mutual conversion of A and C. 4
Answer
(c)

Here, B is Toluene. Reaction of toluene with chlorine in boiling state is as follows

(d)

Here, compound A is benzene and compound C is benzoic acid.

(i) Conversion of C from A:

48
 (ii) Conversion of A from C:

04. (i) 𝐀 + 𝐁𝐫𝟐 + 𝐊𝐎𝐇 → 𝐗 + 𝐊𝐁𝐫 + 𝐊 𝟐 𝐂𝐎𝟑 + 𝐇𝟐 𝐎 [RB’23]

(ii) 𝐁 + 𝐁𝐫𝟐 + 𝐊𝐎𝐇 → 𝐘 + 𝐊𝐁𝐫 + 𝐊 𝟐 𝐂𝐎𝟑 + 𝐇𝟐 𝐎
[A and B compound are aliphatic and aromatic amide]
(c) Which one between X and Y is more basic? Explain with reasons. 3
(d) Why nitration of compound Y occurs in meta position though its substituent is ortho-para
directing? Explain. 4
Answer
(c)

Here, X ⇒ CH3 − NH2

Y⇒

Between CH3 − NH2 ও C6 H5 − NH2 , CH3 − NH2 is more basic.

Electron density in N-atom increases due to the positive induction of alkyl radical like- −CH3. On the other hand,
basic nature of aromatic compound amine like aniline (C6 H5NH2 ) decreases from that of CH3 NH2.Because,
lone pair electron of N-atom present in − NH2 radical of aniline takes part in resonance of benzene ring. As a
result, electron density decreases in N atom. So, dissociation constant pK b of aniline increases and becomes much
more than that of methyl amine (CH3 − NH2 ) .

(d) Y compound is ortho-para indicator. Remaining part is similar to the (c) of board question no. 01, T-07.

05. [Ctg.B’23]

(c) There are 3 𝛑-bonds in the compound A of the stem — Explain with necessary reactions. 3
(d) Which of the compound between A and B in the stem is more reactive to electrophilic substitution
reaction? Analyze. 4
Answer
(c) C6 H5 OH + Zn → C6 H6 + ZnO
(A)
Compound A of the stem us benzene.
Hydrogen addition: Benzene vapor and H2 reacts to produce cyclo-hexane in presence of Ni catalyst at 200°C
temperature.

49
 Halogen addition: Insecticide benzene hexa chloride or Gammaxene powder or lindane powder is produced due
to reaction of 1 molecule of benzene with 3 chlorine molecule in presence of sunlight or ultra violet ray.

From the above addition reaction of H2 and Cl2, it can be understood that there are three pi bonds in the benzene
molecule i.e. benzene is an unsaturated hydrocarbon.
(d) Completing the next part of the reaction,

Effect of – NO2 radical in nitro-benzene:

Benzene draws the electron cloud toward itself due to negative mesomeric effect present in nitro radical. Then
resonance occurs in benzene ring in the following way. As a result, electron density at ortho-para position
decreases according to II-IV resonating structure; i.e., benzene ring becomes somewhat inactive. Then electron
density at meta position becomes more comparatively. As a result, electrophile can cause substitution in meta
position.

For example, nitro benzene is produced if nitration of benzene is carried at 60°C-temperature. But if nitration of
benzene occurs at 100° C -temperature 1, 3 dinitro benzene is produced. It is proved from here that nitro-benzene
is less reactive than that of benzene. That is, A > B.

conc.H2 SO4
→
100℃

𝐅𝐞 𝐭𝐮𝐛𝐞 𝐇𝐍𝐎𝟑 , ∆
06. 𝐏→ 𝐐→ 𝐑 [BB’23]
𝟒𝟓𝟎°𝐂 𝐇𝟐 𝐒𝐎𝟒
Here, P is an unsaturated hydrocarbon of 2 carbon.
(c) Explain the mechanism of preparing R from Q. 3
(d) Which one of the compounds between Q and R is more reactive toward electrophilic substitution
reaction? Analyze. 4
Answer
(c) Completing the reaction of the stem,

Mechanism of producing R from Q i.e., nitrobenzene from benzene-

Step-1: Preparation of electrophile:
+
H2 SO4 + HO − NO2 → NO2 + H2 O + HSO−
4

50
 Step-2: σ- complex preparation:

Step-3: Formation of additive compound:

NO2

(d) Q in the stem is and R is

Remaining part is similar to the (d) of board question no. 05, T-07.

𝐙𝐧 𝐂𝐨𝐧𝐜. 𝐇𝐍𝐎𝟑
07. → 𝐁→ 𝐂 [JB’23]
∆ 𝐂𝐨𝐧𝐜. 𝐇𝟐 𝐒𝐎𝟒 .∆

(c) Describe the reactions of producing A from B with equations. 3

(d) Analyze the reason of different position of substituent in electrophilic substitution reaction of A
and C compound with mechanisms. 4
Answer
(c) Completing the reaction, we get:

That means, benzene from phenol:

Chlorobenzene is produced in presence of FeCl3 by the reaction of Cl2 with benzene.

Phenol is produced if chlorobenzene is reacted in presence of NaOH.

(d) Completing the reaction, of the stem we get:

Here A is phenol and C is nitro-benzene;

51
 Effect of – NO2 radical in nitrobenzene:
The electron cloud of the benzene ring is drawn towards itself due to the negative mesomeric effect of the nitro
radical. Then the resonance in the benzene ring occurs as follows. As a result, electron density decreases in the
ortho and para positions in resonance structures II-IV; That is, the benzene ring is somewhat inactive. Then the
electron density is relatively higher in the meta position. Therefore, electrophiles can cause substitution at the
meta position

On the other hand, the positive mesomeric effect of the hydroxyl group in phenol pushes the electron cloud of
the benzene ring towards benzene. Then the resonance in the benzene ring occurs as follows. As a result, the
electron density in the ortho and para positions of the resonance structure increases, i.e. the benzene ring is slightly
activated. Therefore, electrophiles can cause substitution at the ortho-para position.

𝐙𝐧 𝐝𝐮𝐬𝐭 𝐍𝐢𝐭𝐫𝐚𝐭𝐢𝐨𝐧 𝐒𝐧+𝐇𝐂𝐥

08. 𝐂𝟔 𝐇𝟓 𝐎𝐇 → 𝐀→ 𝐁→ 𝐂 [CB’23]
(c) Explain the preparation of B from A. 3
(d) Analyze the order of reactivity between B and C toward electrophilic substitution reaction. 4
Answer
(c) Completing the 1st part of the reaction in the stem,

Remaining part is similar to the (c) of board question no. 06, T-07.
(d)

Here, B is nitrobenzene and C is aniline. −NH2 is a benzene ring activating group. Its resonance is as follows -

I II III IV V
−NH2 radical pushes its lone pair cloud into the benzene ring by positive mesomeric effect. Then according to
II-IV the benzene ring is activated by increasing the electron density in the ortho-para position. On the other hand,
−NO2 is a benzene ring deactivating group. Its resonance is as follows-

52
 (I) (II) (III) (IV) (V)
The −NO2 radical pulls the electron cloud of the benzene ring towards itself by the negative mesomeric effect.
As a result, the electron density in the ortho-para position is reduced according to resonance structure II-IV; As
a result, the benzene ring is deactivated. That is why it is more inactive than benzene.
∴ Order of reactivity will be B < C.
09. [Din.B’23]

(c) Describe the mechanism of preparing Q from P. 3

(d) Analyze the reactivity order of P, Q and R compound in case of electrophilic substitution reaction. 4
Answer
(c) By completing the reaction of the stem, we get-
sodalime dry AlCl3
C6 H5 COONa → C6 H6 →
∆ CH3 Cl
(P) (Q)
+
Step-1: formation of electrophile: CH3 Cl + AlCl3 → CH3 (Ep) + AlCl−
4

Step-2: σ − complex formation:

Step-3: elimination of H:

(d) Between R and Q, Q compound is more reactive to electrophilic substitution reaction. Resonance occurs in
benzene ring because of methyl radical (−CH3 ). Then the benzene ring becomes more active due to the increase
of charge density in ortho and para position. In this case, though methyl radical (−CH3 ) has no lone pair electron,
the sigma (σ) electron of C-H bond in −CH3 radical attached with the conjugate double bond of benzene takes
part in hyper conjugative or ‘bondless’ resonance of benzene ring and toluene becomes more active than that of
benzene.

The electron cloud of the benzene ring is drawn towards itself due to the negative mesomeric effect of the nitro
radical. Then resonance occurs in the benzene ring. As a result, electron density decreases in ortho and para
positions according to resonance structure II-IV; That is, the benzene ring becomes somewhat inactive. Then the
electron density is relatively higher in the meta position. Therefore, electrophiles can cause substitution at the
meta position.

53
 For example: If nitration of benzene occurs at 60°C- temperature, nitrobenzene is produced. But 1, 3-dinitro
benzene is produced if nitration of nitrobenzene occurs. It’s proved by this, nitration is less effective in
nitrobenzene than that of benzene at 100°C temperature.

That means, nitrobenzene is less reactive than benzene. So, order of reactivity: Q > P > R
∆ 𝐐 𝐂𝐥𝟐
10. P (Carbolic acid) + 𝐙𝐧 → 𝐌𝐚𝐣𝐨𝐫 𝐩𝐫𝐨𝐝𝐮𝐜𝐭 → 𝐑 + 𝐇𝐂𝐥 [MB’23]
𝐚𝐧𝐡𝐲𝐝𝐫𝐨𝐮𝐬 𝐅𝐞𝐂𝐥𝟑
(c) Explain the mechanism of preparing compound R form Q of the stem. 3
(d) Analyze in which of the compound between Q and R nitration occurs easily. 4
Answer
(c) Completing the first part of the reaction, we get:

Chlorination of benzene:
In first step, electrophile chloronium ion (Cl+ ) is produced.
Cl: Cl + AlCl3 → Cl+ + AlCl−
4
Electrophile Nucleophile
Sigma complex is formed in the 2nd step by attraction of electron in benzenoid ring.

In the last step, product chlorobenzene is produced by elimination of proton from 𝜎 complex in contact of
nucleophile.

(d) In the stem, Q → benzene, R → chlorobenzene:

Chlorobenzene is more active between benzene and chlorobenzene as it is ortho para directing.
Effect of Cl in benzene ring of chlorobenzene: The positive mesomeric effect of chlorobenzene causes the
electron cloud of chlorine to push towards the benzene ring. The following resonance occurs in the benzene ring,
resulting in increased electron density in the ortho and para positions in the resonance structure. That is, the
benzene ring is slightly activated. As a result, electrophilic substitution occurs faster in chlorobenzene than in
benzene.

For example: Though about 60℃ temperature is needed for nitration of benzene, chlorobenzene needs less
temperature.

54
11. [DB’22]

∆ 𝐂𝐇𝟑 𝐂𝐥
+ 𝐍𝐚𝐎𝐇(𝐂𝐚𝐎) → ‘Y’ → ‘Z’ + HCl
𝐝𝐫𝐲 𝐀𝐥𝐂𝟑

(c) Explain the mechanism for formation of Z from Y. 3

(d) Analyze with reasons which of compounds Y and Z undergoes nitration more easily. 4
Answer

(c)

The Friedel-Crafts alkylation reaction of Y to Z is an electrophilic substitution reaction. Remaining part is similar to
the (c) of board question no. 09, T-07.
(d) Y is benzene and Z is methyl benzene. Resonance occurs in the benzene ring under the influence of the methyl
group. That is, the electron density increases in the ortho and para positions. Electrophiles, during nitration
(−NO2) group is easily attracted at these sites. As a result, the reaction occurs easily.

Resonance:

Nitration of benzene: Nitration of benzene occurs at 60℃ temperature.

conc.H2 SO4
+HNO3 →
60℃

Nitration of Toluene: Nitration in toluene is carried out at a lower temperature (30°C) than nitration in benzene
(60°C). and −NO2 can easily attach to the ortho and para positions.

Between Y and Z nitration occurs more easily in Z compound.

12. [RB’22]
[X = Sodium salt of carboxylic acid]
(c) Discuss the mechanism of preparation of Z from Y. 3
(d) Nitration of Y and Z gives different products—explain with resonance. 4
Answer
(c)

Remaining part is similar to the (c) of board question no. 06, T-07.

55
(d) Nitro group attracts the π (pi) electron of the benzene ring towards itself due to positive mesomeric effect. Then
the benzene ring resonates as follows. And, the electron density in the meta position increases and the electrophile
is added to the meta position.

Nitration of nitrobenzene at 100℃ results in addition of the nitro group to the meta position.

But on nitration of benzene,

Thus, nitration of Y and Z gives different products as the −NO2 radical is meta-directing due to resonance.

13. Observe the following stem and answer the questions: [Ctg.B’22]
𝐬𝐨𝐝𝐚𝐥𝐢𝐦𝐞
(i) 𝐂𝟔 𝐇𝟓 𝐂𝐎𝐎𝐍𝐚 → ‘𝐏’ + 𝐍𝐚𝟐 𝐂𝐎𝟑
𝚫
𝐝𝐫𝐲 𝐞𝐭𝐡𝐞𝐫
(ii) 𝐂𝟔 𝐇𝟓 𝐂𝐥 + 𝐂𝐇𝟑 𝐂𝐥 → ‘𝐐’ + 𝐍𝐚𝐂𝐥
𝐍𝐚 𝐦𝐞𝐭𝐚𝐥
(d) In electrophilic substitution reaction, ‘Q’ compound is more reactive than ‘P’ compound – Explain
the statement with resonance figures. 4
Answer
(d)

(i)

(ii)

Methyl group (CH3 −) is a benzene ring activating group. Due to increase of electron density at the ortho and
para, position, methyl benzene is more reactive than benzene.

Here, in the resonance, the electron density increases in ortho-para position, for which electrophiles get attracted
easily. Therefore, in the electrophilic substitution reaction, the Q (Toluene) is more reactive than P (Benzene).

56
14. [BB’22]

(c) Explain the mechanism of preparing D from B. 3

(d) Between compounds - C and D, which one is more reactive in Electrophilic substitution reaction?
Analyze. 4
Answer
(c) Similar to the (c) of board question no: 09, T-07.

Here,

(d)

Between C and D, compound D is more reactive in electrophilic substitution reaction. Due to the influence of the
methyl (−CH3 ) radical, resonance in the benzene ring occurs as follows.

I II III IV V
Then the electron density in the ortho and para position increases and the benzene ring become more active. In
this case, although the (−CH3 ) radical has no lone pair electrons, the sigma (σ) electrons of the (C − H) bond of
the (−CH3 ) radical attached to the conjugate double bond of benzene participate in a special resonance called
hyper conjugative or 'non-bonding' resonance in the benzene ring and as a result, toluene is more reactive than
benzene.
The electron cloud of the benzene ring is drawn towards itself due to the negative mesomeric effect of the nitro
group. Then the resonance in the benzene ring occurs as follows.

As a result, electron density decreases in ortho and para positions according to resonance structure II-IV; That is,
the benzene ring becomes somewhat inactive. Then the electron density is relatively higher in the meta position.
Therefore, electrophiles can cause substitution at the meta position.

57
 For example, nitration of benzene at 60°C yields nitrobenzene. But nitrobenzene yields 1, 3-dinitrobenzene at
100℃. This proves that at 100°C, nitrobenzene is less active than benzene in nitration.

That is, nitrobenzene is less active than benzene.

Hence, in the electrophilic substitution reaction, compound D is more active between compounds C and D.
15. [Din.B’22]

(c) How can benzene be produced from compound ‘A’? 3

Answer
(c) Compound A is Cn Hn where if n = 2 then C2 H2 (ethyne).
Reaction to produce benzene from ethyne: At 450°C temperature if ethyne is passed through heated iron pipe
then benzene is produced.
Fe
3 CH ≡ CH → C6 H6
400°C

Mechanism:

16. [Din.B’22]

(c) Explain the reaction mechanism of preparing ‘A’. 3

(d) Which one between ‘A’ and ‘B’ will produce ortho-para isomer by electrophilic substitution
reaction? Analyze. 4
Answer
(c) Similar to the (c) of board question no. 06, T-07.

Where, Mechanism of nitration

(d) Similar to the (d) of board question no. 09, T-07.

Where,

58
17. Answer according to the stem: [MB’22]

(c) Discuss the mechanism for producing compound B from A. 3

(d) In which position will the 2nd substituent of compound C go? Explain with resonance structure. 4
Answer
(c) Similar to the (c) of board question no: 09, T-07.

A= ,B=

(d) Compound A obtained from (c) is benzene.

Remaining part is similar to the (d) of board question no. 12. T-07.

18. [DB’21]

𝐀 = containing with 2 carbon alkyene

(c) Explain the mechanism of preparation of C compound from B compound. 3
(d) In electrophilic substitution reaction which compound is more reactive between C and D. Explain
with resonance. 4
Answer
(c) The mechanism of preparation of compound C from B is similar to the (c) of board question no. 06, T-07.
(d) According to the stem, compound C is nitrobenzene and D is toluene. Remaining part is similar to the (d) of
board question no. 14, T-07.

19. Answer the questions according to the stem: [RB’21]

𝐅𝐞
(i) 𝐂𝐇 ≡ 𝐂𝐇 → 𝐀
𝟒𝟓𝟎°𝐂
NO2

𝐜𝐨𝐧𝐜 𝐇𝟐 𝐒𝐎𝟒
(ii) 𝐀 + 𝐇𝐍𝐎𝟑 → +𝐇𝟐 𝐎
𝟔𝟎°𝐂

(c) Is the A-compound of the stem aromatic or not? Explain. 3

(d) Analyze the mechanism of reaction no. (ii). 4

59
 Answer

(c) 3CH CH Fe
450°C
Benzene is an aromatic compound, its explanation is:
(i) Benzene has (4n + 2) number of delocalized π electrons.
Number of delocalized π electrons
4n + 2 = 4 × 1 + 2 = 6; ∴ n = 1
∴ Benzene has 6 delocalized π electrons.
(ii) The structure of benzene is planar cyclic
(iii) Conjugate double bonds exist.
(iv) Does not give addition reactions like alkenes.
(v) Participates in electrophilic substitution reactions.
So, benzene is an aromatic compound.

(d) Mechanism of reaction no. (ii) is similar to the (c) of board question no. 06, T-07.
𝐍𝐢𝐭𝐫𝐚𝐭𝐢𝐨𝐧 𝐫𝐞𝐝𝐮𝐜𝐭𝐢𝐨𝐧
20. 𝐂𝟔 𝐇𝟔 → 𝐘→ 𝐙 [Ctg.B’21]
’𝐗’ [𝐇]
(c) Explain the mechanism of preparation of compound 'Y' in the stem. 3
(d) Discuss the order of reactivity of compounds X, Y and Z in electrophilic substitution reactions. 4
Answer
(c) The mechanism of preparation of compound Y in the stem is similar to the (c) of board question no: 06, T-07.
(d) Completing the reaction we get,
Nitration reduction
C6 H6 → C6 H5 − NO2 → C6 H5 − NH2
X Y [H] Z

Aniline i.e., compound Z is more reactive and Y i.e., nitrobenzene is the least reactive in electrophilic substitution
reaction. That is, the order of reactivity is Z > X > Y
−NH2 is a benzene ring activating group. Its resonance is as follows-

The −NH2 group pushes its lone electron pair cloud into the benzene ring by positive mesomeric results. Then
according to structure II-IV the electron density in ortho-para position increases and the benzene ring is activated.
On the other hand −NO2 is a benzene ring deactivating group. Its resonance is as follows-

(I) (II) (III) (IV) (V)

−NO2 group attracts electron cloud of benzene ring towards itself by negative mesomeric effect. As a result, the
electron density decreases in the ortho, para position according to resonance structure II-IV; That’s why, the
benzene ring is deactivated. That is why it is less reactive than benzene. Hence the order of reactivity of X, Y, Z
is Z > X > Y.

60
 𝟒𝟓𝟎°𝐂 𝐂𝐇𝟑 𝐂𝐎𝐂𝐥
21. 𝐂𝟐 𝐇𝟐 → 𝐀→ 𝐁 [Ctg.B’21]
𝐅𝐞 𝐀𝐥𝐂𝐥𝟑

(c) Write down the equation for the preparation of 'Gammaxene' from 'A' compound. 3
(d) Explain preparation of 'B' compound of the stem with mechanism. 4
Answer
450°C
(c) Completing the first part of the reaction of the stem, C2 H2 → C6 H6
Fe benzene (A)

One molecule of benzene reacts with three Cl2 in the presence of bright sunlight or ultraviolet light to produce
the disinfectant benzene hexachloride or gammaxene powder.

hv
3Cl2 →

Gammaxene (C6 H6 Cl6 )

450°C CH3 COCl
(d) Completing the stem reaction we get, C2 H2 → C6 H6 C6 H5 − COCH3
Fe benzene(A) AlCl3 acetophenone(B)

The process of making acetophenone from benzene is the Friedel-craft acylation reaction. Its mechanism is as
follows-
Step-1: Formation of electrophile:
O O
|| ||
CH3 − C − Cl + AlCl3 → CH3 − C + + AlCl−
4
Step-2: Formation of carbonium ion:

(A)
Step-3: Elimination of proton:

(B)

𝐍𝐚𝐎𝐇/𝐂𝐚𝐎 𝐂𝐇𝟑 𝐂𝐥
22. COONa → 𝐗→ 𝐘 [CB’21]
△ 𝐚𝐧𝐡𝐲𝐝𝐫𝐨𝐮𝐬 𝐀𝐥𝐂𝐥𝟑
𝐝𝐫𝐲 𝐞𝐭𝐡𝐞𝐫
𝟐𝐂𝐇𝟑 𝐂𝐥 + 𝟐𝐍𝐚 → 𝐙 + 𝟐𝐍𝐚𝐂𝐥
(d) Which of X and Y is more reactive in the electrophilic substitution reaction? Analyze. 4
Answer
(d) According to stem, compound X is benzene and Y compound is toluene. Remaining part is similar to the (d)
of board question no: 13, T-07.

61
 Conc. HNO3 Conc. HNO
23. Conc. H2SO4 ‘A’ Conc. H SO3 B [JB’21]
2 4

(c) Explain the position of the second substituent in compound B. 3

(d) Explain with equation the mechanism of production of compound ‘A’. 4
Answer
(c) Explanation of position of second substituent of compound B is similar to the (d) of board question no. 12, T-07.

(d) Explanation of mechanism of producing compound ‘A’ with reaction is similar to the (c) of board question
no. 06, T-07.
24. [BB’21]

(c) Explain the reason for the use of anhydrous 𝐀𝐥𝐂𝐥𝟑 catalyst in catalytic reactions. 3
(d) Which of A and B is more active in electrophilic substitution reaction? Explain? 4
Answer
(c) According to stem A is benzene (C6 H6 ) and the reaction is Friedel-Crafts Alkylation.
Anhydrous AlCl3 is used in this reaction because the electrophile produced in this reaction combines with
anhydrous AlCl3 to form a temporary molecule, and later when benzene wants to regain its aromaticity, a charged
atom from that temporary molecule is transferred to hold an H+ . When AlCl3 is hydrated, the lone pair e− of H2
forms coordinate bonds with the empty 3pz orbital and 3d subshell of Al. So AlCl3 cannot act as an electrophile
in the presence of H2 O.
Al(13) → 1s2 2s2 2p6 3s13p1x 3p1y 3p0z 3dxy
0 0
3dyz 0
3dzx 3d0x2−y2 3d0z2

Thus AlCl3 accelerates the reaction by retaining an electrophile. Hence AlCl3 is used in the appropriate reaction.
(d) According to stem compound A is benzene and B is toluene. The remaining part is similar to the (d) of board
question no: 13, T-07.
𝐒𝐧 𝐒𝐧
25. (i) 𝐑 − 𝐍𝐎𝟐 + [𝐇] → 𝐀 (ii) 𝐀𝐫 − 𝐍𝐎𝟐 + [𝐇] → 𝐁 [SB’21]
𝐇𝐂𝐥 𝐇𝐂𝐥
(d) Do the Nitration and chlorination reactions of B undergo substitution reaction at the same
position? Show logic. 4
Answer
(d) The compound B of the stem is Aniline. Nitration and chlorination reactions of aniline will have their substitution
in different places. If aniline is heated to a temperature of 60-70℃ with HNO3 and H2 SO4, it produces meta-
nitroaniline.

62
 +
In the presence of acid, aniline first produces anilinium ion (C6H5 NH3 ) which is a meta-indicating group.
Therefore, during nitration of aniline substitution takes place in meta position. In the presence of iron (III) chloride
(FeCl3) and at room temperature, the addition of chlorine gas (Cl2) to liquid aniline results in the formation of
ortho-para chloro aniline through substitution.

−NH2 is an ortho-para indicating group, so substitution takes place in the ortho-para position.
Therefore, nitration and chlorination reactions of the compound B of the stem, aniline do not take place in the
same position.
26. [SB’21]

𝐅𝐞
𝐆𝐚𝐬 𝐀 → 𝐁
𝟒𝟓𝟎℃

(c) Explain the mechanism of preparation of compound C from compound B. 3

(d) Explain using reactions which is more reactive in the substitution reaction between compounds C
and D. 4
Answer

(c) Similar to the (c) of board question no. 06, T-07. 𝐁 = ,𝐂 =

(d) Similar to the (d) of board question no. 14, T-07. 𝐃 =

27. [Din.B’21]

∆
𝐂𝟔 𝐇𝟓 𝐂𝐎𝐎𝐍𝐚 + 𝐍𝐚𝐎𝐇 (𝐂𝐚𝐎) → 𝐗

(c) How to prepare aniline from catalyst X? Describe with equation. 3

(d) Which of Y and Z is more reactive in the electrophilic substitution reaction? Analyze with
resonance. 4
Answer
(c) By completing the reaction of the stem,

∆
C6 H5 COONa + NaOH(CaO) → C6 H6
X

63
 Here, X is benzene. The preparation of aniline from benzene is as follows:
Nitrobenzene must first be prepared by nitration of benzene.
NO2NO2
HNOHNOH 2SOH
conc. 2
4SO
H2 SO
4 4
+HNO 33 → 3
Benzene Nitro- Benzene
Aniline is then prepared by oxidation of nitrobenzene.
Sn + 4HCl → SnCl4 + 4[H]

(d) According to the stem, Y is nitrobenzene and Z is toluene. The remaining part is similar to the (d) of board
question no. 14, T-07.
𝐈𝐫𝐨𝐧 𝐭𝐮𝐛𝐞 𝐇𝐍𝐎𝟑
28. 𝐏→ 𝐐→ 𝐑 [MB’21]
𝟒𝟎𝟎°𝐂 𝐇𝟐 𝐒𝐎𝟒
Here P is an alkyne molecule with 2 carbons.
(c) Show that Q molecule is a special kind of unsaturated compound. 3
(d) Between the electrophilic substitution of Q and R, explain the reason for the difference between
positions of substituents. 4
Answer
(c) Here Q is benzene. Benzene is a special type of unsaturated compound.
Fe
3CH ≡ CH →
400°C

Molecules of aromatic compounds show a special type of unsaturation. Although benzene contains three double
bond they do not perform reaction as fast as ethene (CH2 = CH2 ) molecules. Benzene molecule, despite
udergoing addition reaction with H2 , X 2 and O2 it does not do so with HCl, HBr, H2 SO4 , R − X etc. It does not
even show unsaturation test of organic compounds, Bayer test and Bromine water test.
(d) Between the electrophilic substitution of Q and R, explain the reason for the difference between positions of
substituents is similar to the (d) of board question no: 07, T-07.
29. [RB’19]
COO Na HNO3 Y Sn A
H2SO4 HCl
NaOH . CaO
X
CH3Cl strong oxidation
Z B
AlCl3
(c) Write down the identification test of functional group of ‘A’ with chemical equation. 3
(d) Explain if nitration of A and B compound is done then will the substitute attach in the same
position or not? 4
Answer
(c)
COONa NO2
NaOH HNO3 Sn+HCl
→ → → NH2
CaO H2 SO4
X Y A

64
 In the stem, ‘A’ is phenyl amine or aniline. Two tests are shown below to identify the functional group:
N=C
NH2
60°C
(1) Carbyl amine test: +CHCl3 + KOH(alc. ) → + KCl + H2 O
carbyl amine
Carbyl amine or phenyl iso cyanide is produced with bad smell by which aniline can be identified.
NH2 N2 Cl
0−5°C
(2) + HCl + NaNO2 →
NH2 OH
40°C
+ HCl + NaNO2 → + N2 ↑
∴ If aniline is reacted with HCl and at low temperature then diazonium salt is obtained, again at high temperature
phenol is obtained in place of diazonium salt.
(d)
NO2 NH2
HNO3 Sn
H2SO4 HCl
COONa
A
NaOH+CaO
→ CH3 COOH
X
CH3Cl strong
AlCl3 oxidation
Z
Nitration reaction is mainly electrophilic substitution reaction and even though −NH2 group is an ortho-para
indicating group −COOH group is meta indicating group.
−NH2 group is mainly + M effect creating group, for which lone pair electron in N atom in N̈H2 − group moves
towards benzene ring. It is shown below in the fig:
+ + +
- NH2 NH2 NH2
N H2 NH2
C C
C C C
CH CH CH CH
CH CH CH CH CH CH
CH CH CH CH
CH CH CH CH CH CH
CH CH
CH CH CH
(1) (2) (3) (4) (5)
From structure 2,3 and 4 we see, negative charge is created in position 2,4,6 due to the donated electron i.e., for
electron density is more in 2,4,6 position or in ortho-para position in benzene ring for −NH2 group.
Again –COOH is –M effecting group for which it takes electron towards itself from benzene ring.
It is shown below in the fig:
O O O O O

C OH C OH C OH C OH C OH

(1) (2) (3) (4) (5)

From the figure we see, at 2,3,4 structure positive charge is created in 2,4,6 position in benzene ring i.e., −COOH
group attracted electron towards itself and electron density thus reduces in benzene ring. Thus, electron density
increases in meta position and electrophiles attach at meta position.
65
 COOH COOH
H2 SO4
+ HNO3 →
NO2

Even though −NH2 group is orho-para indicating, in nitration of aniline −NO2 group attaches at meta position
+
NH3

because the proton produced in reaction between HNO3 and H2 SO4 adds with NH2 and produces . This

anilinium ion is mainly meta indicating. Thus, even though −NH2 is ortho-para directing but during nitration
anilinium is produced for which −NH2 group sits in meta position of aniline.
NH2 NH2
𝑐𝑜𝑛𝑐. H2 SO4
+HNO3 →
NO2

So, if nitration occurs in A and B then substitute will attach in the same position.
𝐇𝟐 𝐎 𝐅𝐞 𝐭𝐮𝐛𝐞 𝐚𝐧𝐡𝐲𝐝𝐫𝐨𝐮𝐬 𝐀𝐥𝐂𝐥𝟑
30. 𝐂𝐚𝐂𝟐 → M (gas) → 𝐍→ 𝐋 [Ctg.B’19]
𝟒𝟓𝟎°𝐂 𝐂𝐇𝟑 𝐂𝐥

(d) Which one among ‘L’ and ‘N’ is more active in nitration reaction? Explain. 4
Answer
(d) According to the stem, compound N is Benzene and L is methyl benzene. Remaining part is Similar to the (d)
of board question no. 11, T-07.

31. [JB’19]
NaOH(aq), 350ºC, 150 atm
S
𝐅𝐞 𝐂𝐥𝟐 +HCl
𝟑𝐏 → 𝐐→ 𝐑 NH3, Cu2O
𝟒𝟎𝟎°𝐂 𝐅𝐞𝐂𝐥𝟑
T
200ºC, High pressure
P = acidic hydrocarbon containing 2 carbon.
(c) T- is basic but S- is acidic- why? 3
(d) In nitration reaction, S forms ortho para indicating compound but T forms meta indicating
compound- explain. 4
Answer
OH
NaOH, 350 C (S)
Cl 150atm+HCl
Fe Cl2
(c) 3CH = CH → → NH2
P 400°C
Q R NH3,Cu2O
FeCl3 (T)
200 C
Stem’s S is Phenol which is acidic. The aqueous solution of Phenol is called Carbolic acid. Due to presence of
polar −OH group, phenol shows acidic character.
Phenol’s −OH group remains attached to the benzene ring having sp2 hybridization, which is an electron
attracting group. Due to electronegativity, the electron density on O decreases for which phenol becomes ionized.

66
 For this, H+ is dissociated from the aqueous solution of phenol. The resonance of phenol is shown:
+ + +
OH OH OH OH OH

Here for resonance, O atom has attained a positive state. O is an electronegative substance. H attached to O atom,
from O − H bond with σ bond donates two electron and forms H3 O+ and phenoxide ion. So, phenol is an acid.
Aniline is a base whose N atom in −NH2 group has a lone pair electron. By donating this lone pair or by attaching
with proton it acts as base. Aniline’s K b = 4.2 × 10−10.
(d) S of the stem is Phenol and T is aniline.
The – OH group of phenol is ortho-para indicating. – OH group is both −I and +M influenced, but the effect of
positive mesomeric effect is dominant. The resonance structure is shown:
+OH +OH +OH
OH OH
C C
C C C
CH CH CH CH
CH CH CH CH CH CH
CH CH CH CH
CH CH CH CH CH CH
CH CH
CH CH CH
(1) (2) (3) (4) (5)
From 2,3,4 no. structure we see that, the electron donated by O is creating negative charge on 2,3,4 no. carbon of
benzene that is in ortho-para positions. So, in nitration, due to more negative charge on ortho-para positions,
electrophile attaches at the ortho-para positions.
OH OH OH
NO2
H2 SO4
+HNO3 → +
NO2
On the other hand, even if the −NH2 group present in aniline is ortho-para directing group.
+
NH3

The anilium ion ( ) created due to release of a H+ during nitration is meta directing. So −NO2 group attaches
to the meta positions.
NH2 NH2
H2 SO4
+HNO3 →
NO2

𝐙𝐧 𝐧𝐢𝐭𝐫𝐚𝐭𝐢𝐨𝐧 𝐒𝐧+𝐜𝐨𝐧𝐜. 𝐇𝐂𝐥

32. 𝐀 → 𝐁→ 𝐂→ 𝐃 [Din.B’19]
𝐝𝐢𝐬𝐭𝐢𝐥𝐥𝐚𝐭𝐢𝐨𝐧 𝟔𝟎°𝐂 ∆
‘𝐁’ is trimer of ethyne.
(d) Which one between C and D is more reactive in electrophilic substitution reaction? Explain with
resonance. 4
Answer
(d) In the stem, B is benzene. C is and D is NH2

OH NH2
Zn Nitration Sn+HCl
→ → →
distillation 60°C ∆

Remaining part is similar to the (d) of board question no. 01, T-07.

67
 CQ Knowledge-Based Questions & Sample Answers from Previous Board Exams

01. What is Lucas’ reagent? [DB’23; RB’23; MB’23; SB’21; Ctg.B’21; Din.B’19; CB’17]
Answer: Anhydrous ZnCl2 dissolved in concentrated HCl acid solution is known as Lucas’ reagent.
02. What is racemic mixture? [DB’23; MB’23, 22; DB’22, 17; Ctg.B’22, 19 17; Din.B’22; BB’21; JB’17]
Answer: An equimolar mixture of two enantiomers, which cannot rotate the plane of polarized light and is
optically inactive, is known as racemic mixture.
03. What is enantiomer? [RB’23; Din.B’21; JB’19; Din.B’19]
The two optically active isomers which rotate the plane of polarized light by equal amount but in opposite
direction and equimolar mixture of these two mitigate the specific rotation to zero are known as enantiomers.
04. What is tautomerism? [RB’23; All B.18]
Answer: Tautomerism is a specific type of functional group isomerism where isomers with a particular
functional group spontaneously transform into a compound having completely different functional group and
they both remain in dynamic equilibrium.
05. What is chiral carbon?
[Ctg.B’23, 21, 17; JB’23; CB’23, 21, 19; DB’22, 21; SB’22; BB’22, 17; RB’21; All B.’18; SB’17]
In an organic compound, if all the four atoms or radicals connected with a carbon atom are completely
different then that carbon is known as chiral carbon.
06. What is amide? [Ctg.B’23]
Answer: Compound formed by the substitution reaction between ester and ammonia or amine is known as
amide.
07. What is functional group?
[Ctg.B’23, 22; Din.B’23, 22; JB’22; DB’21; SB’21; MB’21; RB’19, 17; CB’19]
A functional group is an atom or group of atoms within a molecule that carries information, determines it’s
properties and characteristic chemical behavior in every molecule or homologue of same homologous series.
08. What are diastereomers? [SB’23; RB’22]
Diastereomers are two optical isomers of an organic compound with two dissimilar chiral centres differing
in configurations without being each other’s mirror image.
09. What is resonance? [SB’23, 19]
Answer: Resonance is the formation of multiple structures in a molecule of a substance by keeping the
position of the atoms unchanged only by varying the electron arrangement.
10. Write the structure of meso tartaric acid. [SB’23]
Answer: Structure of meso tartaric acid:

11. What is carbanion? [BB’23; Din.B’21]

Answer: In an organic compound, ion having negatively charged carbon atom due to the heterolytic division
of the covalent bond is known as carbanion
12. What is free radical? [BB’23; Din.B’23; Ctg.B’22; JB’22; MB’22; BB’19]
Answer: The charged atoms or radicals produced from homogeneous division are called free radicals.

68
13. What is optical isomerism? [BB’23]
Answer: The type of isomerism in which two or more possible isomers with same molecular formulae,
structural formulae and same physical and chemical properties but differ by their action on plane-polarized
light to rotate the plane of polarized light to rotate the plane of polarized light in different degrees is called
optical isomerism.
14. What is catenation? [JB’23; MB’22; RB’21]
Answer: The process of forming long chains by the bonding between the atoms of an element.
15. Write definition: Nucleophile [JB’23; SB’19]
Answer: An atom or radical with an excess of electrons is called a nucleophile.
16. What is electrophile? [CB’23]
Answer: Reactants that are attracted to electrons and accept electrons during organic reactions are called
electrophiles or electron-withdrawing reagents.
17. What are heterocyclic compounds? [Din.B’23]
Answer: The circular compounds which have one or more carbon atoms along with other atoms such as
oxygen (O), sulfur (S), nitrogen (N) etc. are called heterocyclic compounds.
18. What is aromaticity? [MB’23]
Answer: Special characteristic shown by compounds that follow the conditions of huckel theory is known as
aromaticity.
19. Write down the huckel theory. [RB’22]
Answer: The Huckel theory proposed by chemist Eric Huckel in 1931 presents the idea that the special
property of aromatic compounds, or aromaticity, is expressed in terms of resonant electrons involving in formation
of molecular orbitals. The theory is well known as Huckel theory.
[n = 0, 1, 2, … … … ]
20. What is meta director? [RB’22]
Answer: Some radicals attract electron density of benzene cycle towards them due to which the electron
density at the ortho and para position of the benzene cycle decreases. As a result, the electron density to the
meta position remains comparatively greater and attacking electrophiles attach at the meta position. The
above-mentioned radicals are called benzene cycle deactivating group or meta directing group.
21. Write down the IUPAC name of (𝐂𝐇𝟑 )𝟑 𝐂𝐎𝐇. [RB’22]
Answer: 2-methylpropan-2-ol
22. Write down the formula of d-lactic acid. [RB’22]
Answer:

d – lactic acid
23. What is Tollen’s reagent? [Ctg.B’22]
Answer: Ammonia solution mixed with silver nitrate makes a colorless solution which is called Tollen’s
reagent.

69
24. Write down the structural formula of gammaxene. [SB’22]
Answer:

Benzene Hexachloride, C6 H6 Cl6

25. What is paraffin? [JB’22; CB’22]
Answer: The organic compounds which are chemically less active are known as paraffin. Alkane is
chemically less active, So, they are called paraffin.
26. Write down the formula of 𝟏, 𝟑 − buta-di-ene. [CB’22]
Answer: CH2 = CH − CH = CH2
27. What is isomerization reaction? [Din.B’22]
Answer: The reaction in which the atoms and radicals of a compound rearrange to form new compound
with different structural formula is known as isomerization reaction or rearrangement reaction.
28. What is carbocation? Or What is carbonium ion? [RB’21; CB’21; JB’21; All B’18; JB’17]
Answer: An ion containing a positively charged carbon atom which is formed because of the heterolytic
division of covalent bonds in an organic molecule is called a carbocation.
29. What is meso compound? [CB’21]
Answer: Compounds which, despite having more than one chiral carbon in the compound, superimpose one
part to another and remain optically inactive are called meso compounds.
30. What is isomerism? [JB’21]
Answer: Compounds which have the same molecular formula but due to different structural formula and
three-dimensional arrangement of constituent atoms, they show different physical and chemical properties,
those compounds are called isomers and this property is called isomerism.
31. What is formalin? [SB’21]
Answer: 40% aqueous solution of HCHO is called formalin.
32. Write the definition of homologous series? [CB’19]
Answer: The group of organic compounds formed by same elements having similar properties and a common
functional group with a difference of methylene group (−CH2 −) between two adjacent compounds is called a
homologous series.

CQ Comprehensive Questions & Sample Answers from Previous Board Exams

01. Write the experiment to detect −𝐂𝐎𝐎𝐇 radical in an organic compound with equation. [DB’23]
Answer: In an organic compound, −COOH radical or carboxylic radical can be easily detected with NaHCO3
solution. Compounds containing −COOH radical react with NaHCO3 and release CO2 gas as bubbles.
Released CO2 gas muddles clean limewater. Related reactions are:
CH3 COOH + NaHCO3 → CH3 COONa + CO2 + H2 O
Ca(OH)2 + CO2 → CaCO3 + H2 O
02. Explain the Markovnikov rule- [DB’23]
Answer: During the addition reaction of an asymmetric reagent molecule with an asymmetric unsaturated
compound, the negative part of the reagent is attached to the π-bonded carbon of the unsaturated compound
having the least number of hydrogen atoms. This is known as Markovnikov principle. For example- addition
of HBr with propene forms 2 −bromopropane. Because the second carbon atom in propene has the least
number of hydrogens attached and that’s why negative Br − part of the reagent attaches to this 2 no. carbon
and positive H + part attaches to the 1 no. carbon which has the most number of hydrogens. The reaction is-
CH2 = CH − CH3 + HBr → CH3 − CH − CH3 (90%) + CH3 CH2 CH2 Br(10%)
|
Br

70
 ∖
03. How to transform /𝐂 = 𝐎 radical into – 𝐂𝐇𝟐 – radical? [DB’23; Ctg.B’23]
∖
Answer: – CH2 – radical can be transformed into /C = O radical by clemenson reduction reaction.

04. Why are free radicals so reactive? Explain. [RB’23]

Answer: Free radicals are formed due to the homolytic division of covalent bonds in reagent molecules
because of heat or light.
For example:
As free radicals have unpaired electron, they are very reactive and less stable. Also because of the presence
of unpaired electron, free radicals can participate in forming bonds.
05. Why is chloroform kept in colored glass bottles? [RB’23; SB’22; JB’17]
Answer: Used as anesthetic in surgeries, chloroform is kept in an opaque brown colored jar to keep it away
from phosgene gas mixtures and is well corked by filling to the mouth with CHCl3. As a result, light and air
cannot enter the bottle and chloroform remains pure. In the presence of light, chloroform reacts with O2 and
produces toxic phosgene (COCl2 ) gas and HCl.
light
2CHCl3 (l) + O2 (g) → 2COCl2 (g) + 2HCl (g)
Light cannot enter brown colored bottle. In the absence of light, the above reaction doesn’t occur and that’s
why chloroform is preserved in brown bottles.
06. Why isn’t alkyne-2 acidic? [RB’23]
Answer: Alkyne-2 isn’t acidic as it doesn’t have the ability to substitute hydrogen ion.
For example: in the case of CH2 − C ≡ C − CH3 , the marginal carbons are sp3 hybridised. So, carbon-
hydrogen bonds (C − H) are strongly attached. That’s why, by metal or metallic ions hydrogens in the
marginal carbons aren’t substituted. Thus alkyne=2 isn’t acidic.
NH3
CH3 − C ≡ C − CH3 + Na → no reaction
07. Why is racemic mixture optically inactive? Explain. [Ctg.B’23; Din.B’23; Ctg.B’21; JB’19]
Answer: Those optical isomers that rotate the plane of polarized light in opposite direction are known as
enantiomers and equimolar mixture of enantiomers is known as racemic mixture which is optically inactive. d
and l isomers rotate the plane of polarized light by same amount but as in opposite direction, the net rotation
is zero. That’s why, racemic mixture is optically inactive.
08. Naphthalene is an aromatic compound-explain. [Ctg.B’23, 17; MB’23; DB’19; JB’19]
Answer: According to Huckel’s theory, organic compounds that are flattened or planer cyclic and form rings
and has (4n + 2) numbers of delocalizing π electrons are known as aromatic compounds. From the structure
of naphthalene it can be seen that it has 10 delocalized electrons.
4n + 2 = 10 ⇒ n = 2 ; which is an integer and it follows huckel’s number.
∴ Therefore, according to huckel’s theory naphthalene is an aromatic compound.
09. Propanone shows tautomerism-explain. [Ctg.B’23; Din.B’23 Din.B’22, 19; Ctg.B’21; CB’19]
Answer: In tautomerism isomers having certain functional group spontaneously transform into a compound
having another functional group.
Two isomers of C3 H6 O are CH3 COCH3 and CH3 C(OH) = CH2 show tautomerism.−CO − radical of
CH3 COCH3 transforms into−C = C − and −OH radical or enol radical and stays in dynamic equilibrium.

71
10. 2-pentene shows geometrical isomerism-explain. [SB’23]
Answer: Formula of pentene-2:

It shows cis-trans isomerism.

Because in both the double bonded C, different radical or atoms are attached to the same C atom.

11. Why is methyl amine less basic than dimethyl amine? [SB’23]
Answer: Methyl amine (CH3 − NH2 ) is a 1° amine and dimethyl amine(CH3 − NH − CH3 ) is a 2° amine.
2° amines are more basic than 1° amines. Basicity of amines depends on the density of electron cloud
of N −NH2. In 2° amine, there is an extra −CH3 group than 1° amines and as −CH3 group is electron donating
group electron cloud density of N in −NH2 more and that’s why 2° amine is more basic.
12. Ethanal gives aldol condensation reaction-explain. [BB’23]
Answer: Aldehydes containing α hydrogens show aldol condensation reaction. Ethanal (CH3 − CHO)
contains α hydrogen and goves aldol condensation reaction. For example- in the presence of dilute NaOH
solution, two molecules of ethanol react with each other to form
1,3-hydroxy aldehyde or aldol.
H
| dilute NaOH
CH3 − C = O + H − CH2 − CHO →
20−30°C
OH
|
CH3 − CH − CH2 − CHO
aldol
13. Between aniline and methyl amine which one is more basic? Explain. [BB’23 ’21; Ctg.B19; Din.B’19]
Answer: Between CH3 − NH2 and C6 H5 − NH2 , CH3 − NH2 is more basic.
Alkyl radicals such as CH3− radicals increase the electron density on the N- atom due to its positive inductive
effect. On the other hand, the alkalinity of aromatic amines such as aniline (C6 H5 NH2 ) decreases from
CH3 NH2 . Because the lone electron pair of the N atom of the −NH2 radical of aniline participates in
resonance with the benzene ring. Hence, electron density decreases in N atom. As a result, the dissociation
constant pK b of aniline increases to a much higher value than that of methyl amine (CH3 − NH2 ).
14. Functional groups are the controller of organic reactions-explain. [JB’23]
Answer: A functional group is an atom or group of atoms within a molecule that has a characteristic
chemical behavior and that undergoes the same kind of reactions in every molecule or homologue of same
homologous series.
Compounds of every homologous series has a specific functional group or active group. For example-
functional group of alcohol is −OH. As methanol (CH3 OH), ethanol (CH3 CH2 OH) contain the same
functional group, even though the length and structure of the carbon chain is different the chemical properties
are same. As a result, the chemical reactions are also similar.
15. Ethyne is acidic-explain. [JB’23; CB’23]
Answer: In a hybridized orbital, the more characteristic of s orbital the more overlapping in forming sigma
bond. That’s why, in ethyne molecule carbon-carbon σ bond is strongly attracted by the nucleus of the C
atom. So, the marginal H comes closer to Carbon atom and the bond becomes weak and can be easily broken.
As a result, ethyne is mildly acidic.
CH ≡ CH + 2Na → Na − C ≡ C − Na + H2

72
16. Write the structure of possible isomers of 𝐂𝟑 𝐇𝟖 𝐎 [Din.B’23]
Answer: Possible isomers of C3 H8 O are :
(i) CH3 CH2 CH2 OH → Propanol
(ii) CH3 − CH − CH3 → Propanol-2
|
OH
(iii) CH3 − O − C2 H5 → Ethyl methyl ether
17. Why ethene and propene are mutually homologous? Explain. [MB’23]
Answer: Ethene and propene both are derivatives of aliphatic hydrocarbon alkene. General formula of
alkene is Cn H2n such as: formula of ethene C2 H2×2 and formula of propene C3 H6 or C3 H2×3. Both propene
and ethene has similar formula. There is a difference of methylene group between them. Both of them are
with unsaturated double bond. So, ethene and propene are homologous.
18. Pyrrole is an aromatic compound-Explain. [DB’22]
Answer: The cyclic ring of pyrrole contains (4n + 2) number of delocalized pi electron, for which pyrrole
is an aromatic compound.

Here the lone pair electron of Nitrogen takes part in resonance and the number of delocalized electrons
becomes 6 which satisfies the (4n + 2) number of delocalized electrons for n = 1.
19. Why is meta product found in the nitration of aniline? [DB’22; CB’17]
Answer: The amino group of aniline is ortho-para directing, in this case the nitration will occur at the meta
position. Because aniline reacts with acid first to form anilinium salt. This anilinium group is a meta directing
group. That’s why in the presence of anilinium group, nitration takes place at meta position.

20. Why does But-2-ene show geometric isomerism? [RB’22, 21]

Answer: But-2-ene 3 C − CH = CH − CH3 shows geometric isomerism or cis-trans isomerism.
(H )

Cis isomer Trans isomer

Because it has the formula abC = Cab and since the free rotation along the axis of Carbon-carbon double
bond is not possible, 2 compounds with different configuration are formed.
Therefore, But-2-ene shows geometric isomerism.
21. When two compounds are enantiomers? Explain. [RB’22]
Answer: Optically active isomers of the same compound are called enantiomers of each other.

Here, d-lactic acid and l-lactic acid are enantiomers of each other.

73
22. Why is Aniline a weaker base than ammonia? [Ctg.B’22]
Answer: Basic property or basicity of aromatic amine, such as aniline (C6 H5 − NH2 ) is less than that of
NH3 and aliphatic amines. Because the lone-pair electron of the N atom of −NH2 group of aniline takes part
in resonance of the benzene cycle. So, the electron density in the N atom decreases.
As a result, the dissociation constant pk b of aniline increases (9.4); which is a lot greater than of NH3 (4.
74) methyl amine (CH3 − NH2 ) and dimethyl amine (CH3 )2 NH.

23. Formic acid is a reductant- explain. [Ctg.B’22]

Answer: Due to the presence of the aldehyde functional group (−CHO) in its molecular structure, formic
acid acts as a weak reductant, reduces the weak oxidant, and produces CO2 gas and H2 O by getting oxidized

Hence as weak reductant formic acid reduces Fehling reagent to produce red precipitate of cuprous oxide
(Cu2 O) and reduces Tollen’s regent to form silver mirror just like an aldehyde.
24. Pyridine is an aromatic compound− why? [Ctg.B’22]
Answer: Since pyridine has (4n + 2) number of delocalized pi electrons in its cyclic ring, it is an aromatic
compound.

pyridine
25. Why is Phenol an aromatic compound? Explain. [SB’22; RB’17]
Answer: Phenol is an aromatic compound because according to Huckel’s rule the structure of phenol is flat,
Planar and ring like, and the ring forming atoms have (4n + 2) delocalized π electrons. Phenol has 1 ring
and 6 delocalized π electrons. Because 4n + 2 = (4 × 1 + 2) = 6. Thus phenol is an aromatic compound.
26. Why is 𝐒𝐎𝟑 an electrophile? [SB’22]
Answer: The organic compounds that are attracted by electrons and receive electron are called electrophilic
reagent or electrophile.

Due to presence of 6 electrons in the valence shell of S for SO3 molecule, It has attraction for electrons.
Thus SO3 is an electrophilic reagent.
27. Is 2-bromobutane optically active? Explain. [BB’22]
Answer: As the 2nd carbon of 2-bromobutane has four different groups attached to it, It is a chiral carbon
and the compound is an optically active hydrocarbon.

74
28. Explain: 1-chloro-1-hydroxy ethane is an optically active compound. [BB’22]
Answer:

Here 1st carbon is a chiral carbon which is the main condition of optical isomerism. Thus, the compound is
optically active.
29. Propane and Methane are homologous- Explain. [BB’22; JB’22; CB’17]
Answer: Propane and methane are both homologous compounds of alkane in aliphatic hydrocarbon group.
The general formula of alkane is Cn H2n+2 . Formula of propane is C3 H8or C3 H2×3+2 . Again, the formula of
methane is CH2+2. It is seen that, the formula of propane and methane are similar to the general formula.
So, propane is homologous to methane or homologous to alkane.
30. What kind of isomers are di-methyl ether and ethanol to each other? Explain. [JB’22]
Answer: Dimethyl ether and ethanol are functional group isomers to each other.
Despite having same molecular formula, when two compounds have different functional groups, the
isomerism between the two compounds is called functional group isomerism. They have differences in
physical and chemical properties. For example, between alcohol and ether and among aldehyde, alkenol and
ketone functional group isomerism is seen.
CH3 − O − CH3 CH3 − CH2 − OH
Dimethyl ether Ethanol
31. Why is −𝐎𝐇 group ortho-para director? [CB’22; SB’21]
Answer: If the benzene ring has an -OH radical, the attacking electrophile is attached to the ortho-para
position because the electron concentration increases at the ortho-para position. Therefore, -OH is an ortho-
para director.

32. Which one is more basic between 𝐍𝐇𝟑 and 𝐂𝐇𝟑 𝐍𝐇𝟐 ? Explain. [CB’22]
Answer: Aliphatic amines are more basic than ammonia. Because due to the positive inductive effect of
alkyl radicals such as CH3− the electron density of N-atom increases. Then the basicity of Methyl amine
(CH3 N̈H2 ) and dimethyl amine (CH3 )2 N̈H is greater than ammonia NH3

33. Why is dry ether used in Wurtz reaction? [CB’22; RB’19]

Answer: As Na is a strong metal, it is kept in such a solvent so that it cannot react. If dry ether is not used
then Na metal would react with air and will form Na2 O which hinders the main reaction. That’s why dry
ether is used in Wurtz reaction to keep Na.

75
34. Ethanol and propanol are homologous- Explain. [Din.B’22]
Answer: Every homologous series has the following properties:
(i) They can be expressed by a general formula. Like, Cn H2n+1 OH is the general formula of alcohol. Here,
if n = 1 it is methanol CH3 OH, n = 2 it is ethanol C2 H5 OH.
(ii) The two adjoining homologue have the difference of a methylene radical (−CH2 −). For example, the
difference between methanol (CH3 OH) and ethanol C2 H5 OH) is (−CH2 −) radical.
(iii) Every homologous series has a functional group. Example: −OH is the functional group of alcohols.
(iv) Compounds of every homologous series have common preparation method.
Example:
CH3 I(l) + NaOH(aq) → CH3 OH(l) + NaI(aq)
C2 H5 I(l) + NaOH(aq) → C2 H5 OH(l) + NaI(aq)
(v) They have similarity in their chemical properties. But along with increment in their molecular mass
their melting point, boiling point, density etc. change sequentially. Example: Methanol (CH3 OH) has
boiling point of 65° C, ethanol (C2 H5 OH) 78.3° C.
35. Carbon tetrachloride is an organic compound- Explain. [Din.B’22]
Answer: Carbon tetrachloride (CCl4 ) is formed by substituting H of CH4 with Cl with the help of UV- ray.
Since CCl4 is produced from an organic compound , it is a derivative of organic compound. Thus, it is also an
organic compound.
UV−ray
CH4 + 2Cl2 → CCl4
36. Explain an unsaturation test of organic compounds with reaction. [MB’22]
Answer: (1) Unsaturation test of organic compounds: Bromine (Br2 ) test: Bromine (Br2 ), a dark red liquid
is mixed with carbon tetrachloride (CCl4 )- to create 5% solution. If the red color of the bromine disappears
immediately upon mixing with an organic compound, it indicates the presence of a carbon- carbon double
bond in the compound. For example, when bromine reacts with ethene, which has a double bond. The
electrophilic addition reaction of the bromine in the solution produces colorless 1, 2 -di bromo ethane.
CCl4
CH2 = CH2 + Br2 → CH2 Br − CH2 Br
Ethene 1,2- dibromo ethane
Alkyne molecule has two π bonds, So, bromine test is applicable to alkynes as well.
37. Why is 𝐂𝐥𝐂𝐇𝟐 𝐂𝐎𝐎𝐇 more acidic than 𝐂𝐇𝟑 𝐂𝐎𝐎𝐇 acid? Explain. [MB’22; RB’19]
Answer: In CH3 COOH, −CH3 is electron donating group or group with positive inductive effect. So, in O-H
bond electron cloud moves towards H and O-H bond becomes powerful and does not donate proton easily.
Again, -Cl has negative inductive effect for which shared electron of O-H bond moves towards O and thus
O-H bond becomes weak and can donate proton easily. Therefore, CH2 ClCOOH is stronger acid than
CH3 COOH.
38. Why is alcohol soluble in water? [DB’21; All B’18]
Answer: Due to presence of hydroxyl group the ions present in water can form hydrogen bond. With the
increase of hydrocarbon chain their polarity decreases. For this the small chain hydrocarbon alcohol are
greatly soluble in water. With the increase of hydrocarbon chain their solubility decreases.
39. Why is ethyne slightly acidic? Explain. [DB’21; MB’21; RB’19; All B’18; Ctg.B’17; JB’17]
Answer: In hybrid orbital if the s orbital characteristics are more prominent then in formation of sigma bond
that orbital takes part mostly. For this in ethyne molecule C − C σ bond both C atom nuclei are attracted
greatly. The terminal H atom comes closer to the C atom and the bond becomes weak and thus it can be
broken easily. For this ethyne is partially acidic.
CH ≡ CH + 2Na → NaC ≡ C − Na + H2
76
40. Write the condition of optical isomerism. [DB’21]
Answer: The conditions of optical isomerism are as follows:
(i) Asymmetric carbon atoms or chiral centers are present.
(ii) The configurations of both isomers are mirror images of each other.
(iii) Both configurations should not superimpose on each other.
(iv) A plane light is rotated to the right or left. That is, they are optically active.
41. Which is more basic between 1° amine and 2° amine? Explain [RB’21]
Answer: Between 1° amine and 2° amine, 2° amine is more basic. The basicity of amines depends on the
density of the electron cloud above the N of −NH2 . 2° amines are more basic due to the fact that 2° amines
have an additional −CH3 group compared to 1° and because of the −CH3 electron donating group, the
electron cloud density on the N of −NH2 in 2° amines is higher.
42. Why is −𝐍𝐇𝟐 called ortho-para director? [Ctg.B’21]
Answer: NH2 radical increases the electron density with the help of positive mesomeric effect at the ortho-
para position of the benzene ring. Hence it is called ortho-para indicator. Resonance -
NH2 NH2 NH2 NH2 NH2

43. Explain decarboxylation reaction. [CB’21]

Answer: The reaction in which carbon number is reduced is called de-carboxylation reaction. A reagent is
used in this reaction which is soda lime NaOH(CaO) .
For example:
CaO
CH3 − COONa + NaOH → Na2 CO3 + CH4
Alkanes and Na2 CO3 are produced in this reaction.
44. CH3 is a free radical –Explain. [JB’21]
Answer: Due to the homolytic fission of covalent bonds particular atoms or groups of atoms with unpaired
electrons are formed called free radicals. CH3 is free radical. An example is shown below-
Homolytic Fission
HCl → H +Cl
Homolytic Fission
Cl + H −CH3 → HCl + CH3
NH2

45. Why is −𝐍̈𝐇𝟐 group in this compound alkaline? Explain and write. [JB’21; CB’19]
Answer:
NH2

Here NH2 is an alkaline group. Because it has N which has a pair of lone electrons. Therefore, the
NH2 radical can easily react with acids and donate electrons. That is, it behaves like an alkali.

46. Explain the Clemmensen’s reduction reaction. [BB’21]

Answer: Alkanes can be prepared by reduction of carbonyl compounds i.e. aldehydes and ketones by H atoms
generated from zinc amalgam (Zn.Hg) and concentrated HCl. In this case, the divalent carbonyl radical (−CO−)
is reduced directly to the methylene radical (−CH2− ).This reaction is called Clemmensen’s reduction.
O
|| Zn.Hg
R − C − H/R + 4[H] → R − CH2 − H/R + H2 O
conc. HCl

77
47. Write the test for identification of carbonyl group. [Din.B’21]
Answer: Add 2-3 mL of 2, 4-dinitrophenyl hydrazine in a test tube and add 5-6 drops of the organic
compound. If a yellow-orange precipitate forms, then carbonyl group is present in that compound.

Yellow-orange color
48. What is homologous series? [Din.B’21]
Answer: When organic compounds having the same functional group and chemical property are arranged
in order of their increasing molecular mass, if only one methylene (−CH2 −) group differs between two
consecutive members, the series obtained is called a homologous series.
CH3 − OH
CH3 − CH2 − OH
CH3 − CH2 − CH2 − OH
For example, methanol, ethanol and propanol are homologous to each other.
49. Write carbyl amine test with equation. [Din.B’21; JB’17]
Answer: Chloroform dissolved in 3KOH (alc) reacts with primary amine at 60 − 70°C temperature and
forms a pungent smell of Carbyl Amine.
∆
CH3 − NH2 + CHCl3 + 3KOH (alc. ) →
CH3 − N = C + 3KCl + 3H2 O
Tangent smell
∆
NH2 + CHCl3 + 3KOH (alc. ) →
N = C + 3KCl + 3H2 O
Tangent smell
50. Explain 𝐒𝐍 𝟏 reaction. [MB’21]
Answer: Halogoalkane, alcohol and ether show SN 1 reaction. It is completed in two steps, where in the first
step carbocation is produced and in the second step, nucleophile attaches with the carbocation to form the
product.
CH3 CH3
| Slow |
(i) CH3 − C − X → CH3 − C + + X −
| |
CH3 CH3
CH3 CH3
| Fast |
(ii) CH3 − C+ + OH − → CH3 − C − OH
| |
CH3 CH3
51. Furan is an aromatic compound- explain. [MB’21; Din.B’19]
Answer:
In case of Furan, lone pair electron of O is delocalized.

4n + 2 = 6; n = 1
That’s why, according to Huckel theory furan is an aromatic compound.

78
52. Is a Racemic mixture optically active? Explain. [DB’19]
Answer: The compounds which rotate plane polarized light by an equal amount in opposite directions are
enantiomers, and the mixture of two equimolar enantiomers is called Racemic mixture which is optically
inactive. d and l enantiomers rotate plane polarized light by the same amount but in opposite direction so,
net rotation is zero. As a result, racemic mixture is optically inactive.
53. Why aliphatic 𝟏° amine a base? Explain. [SB’19]
Answer: The nitrogen atom of aliphatic 1° amine can donate electron pair.
H+
↑
CH3 N̈H2 + HCl → CH3 N̈ H2 + Cl− , Since it can donate electron pair, according to Lewis concept, it is a base.
54. What do you mean by Huckel rule? [BB’19]
Answer: According to Huckel rule,
There are to be (4n + 2) numbered delocalized π (pie) electron for an organic compound to be aromatic.
For example, benzene ring has 6 that is, (4 × 1 + 2) π electron electrons and so it is an aromatic compound.
55. Why is −𝐍𝐎𝟐 radical called a metal-directing radical? [BB’19]
Answer: −NO2 radical is meta directing. Because -

The density of electrons electron decrease at ortho-para positions because of resonance due to presence of
−NO2 radical. So, density of electron electron is more comparatively at meta position. For this reason, −NO2
is meta directing.
56. Why is Grignard reagent produced in absence of water? Explain. [CB.’19]
Answer: Grignard reagent explodes in presence of water. It produces huge amount of heat upon reacting
with water.
dry Ether
CH3 Cl + Mg → CH3 MgCl
In presence of water, CH3 Cl reacts with H2 O and produces alcohol. For this reason, Grignard reagent is
prepared in absence of water.
57. Benzene is an aromatic compound – Explain. [All B’18]
Answer: The organic compounds which have circular, coplanar, alternate pie bonds and whose no.
of circulating pie electron is equal to Huckel’s number (4n + 2) are called aromatic compounds
[n = 0,1,2 … … … ]
Benzene has 6 circulating pie electrons.

4n + 2 = 6; n = 1, which is an integer.
So, benzene is an aromatic compound.

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