(ORGANIC CHEMISTRY) CARBONYL COMPOUND

EXERCISE # I
Q.1 Arrange these compounds in decreasing order of reactivity for the nucleophilic attack.
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III
Q.2 In the given reaction

[X] Will be:

(A) HCHO (B)

(C) (D) HCN

Q.3 In the given reaction:

[X] will be:

(A) Only syn oxime (B) Only anti oxime
(C) Mixture of syn and antioxime (D) Secondary amide
Q.4 In the reaction:

[X] Will be:

(A) (B)

(C) (D)

Q.5 Number of aldol products (without counting stereoisomers) in the given reaction:
⊖
OH
C6 H5 CHO + CH3 − CHO ⟶ Product
will be:
(A) One (B) Three (C) Two (D) Four

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Q.6 In the given reaction

(X) and (Y) will respectively be :

(A) CH3 − CH2 − CHO and CH3 − CH2 − CHO
(B) CH3 − CHO and CH3 − CH2 − CHO
(C) CH3 − CHO and CH3 − CHO

(D) CH3 − CHO and

Q.7 Acetophenone can be obtained by the distillation of :

(A) (C6 H5 COO)2 Ca (B) (CH3 COO)2 Ca
(C) (C6 H5 COO)2 Ca and (CH3 COO)2 Ca (D) (C6 H5 COO)2 Ca and (HCOO)2 Ca
Q.8 Gem dihalide on hydrolysis gives :
(A) Vic diol (B) Gem diol (C) Carbonyl compound (D) Carboxylic acid
Q.9 Acetal or ketal is:
(A) Vic dialkoxy compound (B) α, ω-dialkoxy compound
(C) α-alkoxy alcohol (D) Gem dialkoxy compound
Q.10 In the given reaction :

[X] will be :
(A) CH3 − COOC2 H5 (B) CH3 − CH2 − COOC2 H5

(C) Br − CH2 − COOC2 H5 (D)

Q.11 Cross cannizzaro reaction is example of :

(A) Redox reaction (B) Disproportionation
(C) Both (A) and (B) (D) Only oxidation

Q.12 Acetaldehyde can be converted into by which reagent ?

(A) KOH (B) KOH followed by LAH

(C) excess of HCHO and KOH (D) KCN followed by SBH

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Q.13 Product of Perkin reaction is :
(A) α, β-unsaturated aldehyde (B) β-cyclohexyl α, β-unsaturated aldehyde
(C) β-Aryl- α, β-unsaturated acid (D) All of these
Q.14 Which one of the combinations will give propanaldehyde on dry distillation?
(A) (C6 H5 COO)2 Ca and (HCOO)2 Ca
(B) (CH3 COO)2 Ca and (CH3 CH2 − COO)2 Ca
(C) (CH3 − CH2 − COO)2 Ca and (HCOO)2 Ca
(D) (CH3 COO)2 Ca and (CH3 COO)2 Ca
Q.15 In the given reaction:

[X] will be:

(A) Methyl oxide (B) Phorone (C) 1,3, 5-Trimethylbenzene (D) 2-Butyne
Q.16 In the reaction sequence:
→ ( X ) ⎯⎯⎯⎯ → ( Y ) ⎯⎯⎯⎯
( ii ) H2O/Zn→ ( Z )
() 3
hv/Cl2 alc.KOH/  i O
Cyclohexane ⎯⎯⎯

(Z) will be:

(A) Hexanal (B) 2-Hexanone (C) 3-Hexanone (D) Hexanedial
Q.17 Grignard reagents can never give carbonyl compounds with:
(A) CO2 (B) RCOCl (C) RCN (D) RCOOR
Q.18 The given reaction:
() i Zn
C6H5 − CHO + Br − CH2 − COOC2H5 ⎯⎯⎯⎯⎯ →C6H5 − CH = CH − COOC2H5
(ii)HOH/NH4Cl
(iii)

is known as :
(A) Perkin reaction (B) Knoevenagel reaction
(C) Reformatsky reaction (D) Claisen-Schmidt reaction
Q.19 The product of the reaction:

Will be:

(A) C6 H5 − CH = CH − COOH (B)

(C) (D)

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Q.20 Cyanohydrin of which compound on hydrolysis will give lactic acid?
(A) C6 H5 CHO (B) HCHO (C) CH3 CHO (D) CH3 − CH2 − CHO
Q.21 In the given reaction:

(X) and (Y) are:

(A)

(B)

(C)

(D)

Q.22 Acetaldehyde cannot give :

(A) Iodoform test (B) Lucas test (C) Benedict test (D) Tollens test

Q.23 Compound formed by the reaction of furfural with ethanol

is :
(A) an aldol (B) an acetal (C) a ketal (D) a hemiacetal
Q.24 The reaction in which NaCN/C2 H5 OH/HOH is used is :
(A) Perkin reaction (B) Benzoin condensation
(C) Reimer-Tieman reaction (D) Rosenmunds reduction
Q.25 A compound with molecular formula C8 H18 O4 does not give litmus test and does not give colour
with 2,4-DNP. It reacts with excess MeCOCl to give a compound whose vapour density is 152.
Compound A contains how many hydroxy groups?
(A) 1 (B) 2 (C) 3 (D) 4
Q.26 In the reaction sequence:
(C H O)
→( X ) ⎯⎯⎯⎯ →( Y )
KHSO1 / Al
CH2OH − CHOH − CH2OH ⎯⎯⎯ ⎯ 2 5 3


(Y) will be:

(A) CH2 = CH − CHO
(B) CH2 = CH − CH2 OH
(C) Mixture of CH2 = CH − COOH and CH2 = CH − CH2 OH

(D)
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Q.27 Tollen's reagent is used for the differentiation between:
(A) HCHO and CH3 CHO
(B) CH3 COCH3 and CH3 CHO

(C)
(D) HCHO and C6 H5 CHO

Q.28

Identify relationship between A & B products?

(A) Diastereoisomers (B) Enantiomers (C) Positional isomer (D) Identical
Q.29 In the reaction sequence

The product (B) is:

(A) (B) (C) (D)

Q.30 In the reaction

The product (A) is:

(A) (B) (C) (D)

Q.31 Which of the following does not form a stable hydrate by the addition of H2 O ?

(A) (B)

(C) (D)

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Q.32 The conversion
Can be effected by using the reagent

(A) Tollen’s reagent (B) O2 (C) (D)

Q.33 In the reaction

The major product is:

(A) (B)
(C) CH2 = CH − COOCH3 (D) CH3 CH(CN)COCH3

Q.34 (I) (II)

Organic product P & Q are respectively –

(A) (B)

(C) (D)

Q.35 The major product obtained in the reaction is

(A) (B) (C) (D)

Q.36 Total number of stereoisomers of major product (Q) are:

CH3 − CHO + 4HCHO ⎯⎯⎯⎯
NaOH
− HCOONa
→ ( P ) ⎯⎯⎯⎯
2CH3 −CHO
H
→ (Q )

(A) 0 (B) 4 (C) 8 (D) 2

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Q.37 CH3 CHO + NH2 OH → CH3 CH = N − OH
The above reaction occurs satisfactorily at
(A) pH = 1 (B) pH = 4.5 (C) pH = 12 (D) any value of pH
Q.38 An organic compound (A), C5 H10 O, reacts with hydrazine to form a hydrazone derivative (B).
The hydrazone (B) on being heated with KOH at about 180∘ C, gives n-pentane. The compound
(A) does not respond positively to Tollen's reagent and to the iodoform test. The compound (A)
is

(A) (B) (C) (D)

Q.39 The compound having the highest dipole moment is:

(A) (B) (C) (D)

Q.40

(A) (B) (C) (D)

Question No. 41 to 43 (3 questions)

An alkene (A) C16 H16 on ozonolysis gives only product (B) C8 H8 O. (B) also can be obtained by
hydrolysis of the product obtained by reaction between cyano benzene and CH3 MgBr. (A) can
show geometrical isomerism and it can decolourise Br2 water. (B) on treatment with SeO2
produces (C)
Q.41 Which is not correct about (A)?
(A) A is optically inactive
(B) On catalytic hydrogenation 'trans' form of A produces racemic mixture
(C) A can be prepared by Witting reaction on acetophenone with Ph3 P = C(CH3 )Ph.
(D) On treatment with per acid followed by hydrolysis 'trans' form of A produces racemic
mixture
Q.42 Which is not correct about B ?
(A) It gives iodoform test
(B) On treatment with LiAlH4 , H2 O it produces a compound which also responds to iodoform
test.
(C) It gives Tollen's test
(D) On treatment with NH2 NH2 followed by alc. KOH at high temperature, it produces ethyl
benzene
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Q.43 Which is not correct about C ?
(A) On treatment with NaBH4 it will produce a diol.
(B) On treatment with OH − (conc.) followed by acidification racemic mixture of a carboxylic
acid is obtained
(C) It gives Tollen's test
(D) It can take part in aldol condensation

Question No.44 to 48 (5 questions)

Compound 'C' was prepared in a three step sequence from ethyl

trifluoroacetate.
The first step in a sequence involved treating ethyl trifluoroacetate with NH3 to give a
compound A. A on treatment with reagent ' X ' (alongwith gentle heating) produces a
compound B (which on hydrolysis can produce an acid). B on treatment with an orango metallic,
' Y ', followed by hydrolysis produces C. Based on above passing attempt the following
questions:
Q.44 Structutre of 'A' would be

(A) (B)

(C) (D)

Q.45 Structure of B would be

(A) (B) CF3 − C ≡ N (C) CF3 − CH2 − CN (D) CF3 − CH2 − NH2
Q.46 'X' should be
(A) BaO2 (B) H2 O2 (C) P4 O10 (D) N2 O
Q.47 When 'C' is treated with perbenzoic acid it will produce

(A) (B)

(C) (D) (CH3 )3 C − OH

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Q.48

(A) (B)

(C) (D)

(Question No. 49 & 50)

Questions given below consist of two statements each printed as Assertion (A) and Reason (R);
while answering these questions you are required to choose any one of the following four
responses:
(A) If both (A) and (R) are true and (R) is the correct explanation of (A)
(B) If both (A) and (R) are true but (R) is not correct explanation of (A)
(C) If (A) is true but (R) is false
(D) If (A) is false and (R) is true
Q.49 Assertion : Benzaldehyde with HCN gives two isomeric compounds
Reason : Both nitrile and isonitrile compounds are possible when HCN reacts with carbonyl
group.

Q.50 Assertion:

Reason: There are no α − H in this compound, so it can't give aldol.

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EXERCISE # II
Q.1 Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by :
(A) I2 /NaOH (B) NaSO3 H (C) NaCN/HCl (D) 2,4-DNP
Q.2 An optically inactive alcohol (A) C6 H12 O is oxidized by MnO2 to produce optically inactive
carbonyl compound while reduction of (A) by H2 /Ni produces optically active compound.
Possible structure(s) of alcohol is/are
(A) Hex-2-ene-1-ol (B) Hex-3-ene-2-ol
(C) 2-Methyl pent-2 - ene-1-ol (D) 3-Methyl pent-2 - ene-1-ol
Q.3 Consider the structure of given alcohol:

This alcohol can be prepared from:

(A) (B)

(C) (D)

Q.4 Correct option(s) regarding following reaction sequence is/are :

HgSO4 Ba (OH )
CH3C  CH ⎯⎯⎯
H2SO4
→ P ⎯⎯⎯

2
→Q ⎯⎯⎯
NaOH
I2
→ R + S ⎯⎯
6Ag
→T
'x'

(A) T is homologue of ' X ' (B) R is sodium salt of

(C) P can produce S with NaOI (D) R is sodium salt of

Q.5 Which of the following compounds will not give aldol condensation:
(A) Acetaldehyde (B) Formaldehyde (C) Pivaldehyde (D) Crotonaldehyde

Q.6 (A)

In above reaction (A) and (B) will respectively be

(A) (B)

(C) (D)

Q.7 Stability of hydrates of carbonyl compounds depends on:

(A) Steric hindrance (B) Presence of -I group on gemdiol carbon
(C) Intramolecular hydrogen bonding (D) angle strain in carbonyl compound
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Q.8 Which of the following can be used for protection of carbonyl group
(A) CH2 OH − CH2 OH/H ⊕ (B) CH2 OH − CH2 − CH2 OH/H ⊕
(C) HS − (CH2 )3 − SH (D) CH2 OH − CH2 − CHO
Q.9 Which of the following is/are example of 1,4-addition reaction

(A)

(B)

(C)

(D)

Q.10 Which of the following(s) will form stable hemiketal:

(A)

(B)

(C)

(D)
Q.11 Mixture of Ph − CHO&HCHO is treated with NaOH then Cannizzaro reaction involves:
(A) Oxidation of HCHO (B) Reduction of HCHO
(C) Oxidation of Ph − CHO (D) Reduction of Ph − CHO
Q.12 Final product in the given reaction sequence is:

(A) (B)

(C) (D)

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Q.13 Consider the following reaction sequence.

The products (A) and (B) are, respectively,

(A) (B)

(C) (D)

Q.14 Consider the following sequence of reactions.

The products (A) and (B) are, respectively.

(A) (B)

(C) (D)

Q.15 Consider the following sequence of reactions.

The major product (B) is:

(A) (B) (C) (D)

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Q.16 In the reaction
NaOH
(CH3 )2 CHNO2 + HCHO ⟶
the major product is

(A) (CH3 )2 CHCH2 ONO2 (B)

(C) (D)

Q.17 Consider the following sequence of reactions.

The ketone (A) is:

(A) (B) (C) (D)

Q.18 In the reaction

the product (X) is:

(A) (B)

(C) (D)

Q.19

End product (B) of above reaction is:

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(A) (B)

(C) (D)

Q.20

Final Product ‘S’ is –

OH OH OH
OH
(A) (B)
HO
HO HO HO
OH

(C) (D)

Q.21 Which of the following reactions will give(s) 2∘ alcohol as a major product:

(A)

(B)

(C)

(D)

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Q.22 Match list-I with list-II
List-I List-II
Θ
OH Θ
(A) C6 H5 CHO + HCHO ⟶ C6 H5 CH2 OH + HCOO (P) Cannizzaro reaction

(B) (Q) Aldol condensation

(C) (R) Soda-lime Decarboxylation

(D) (S) Benzil benzilic acid rearragement

Q.23 Match list-I with list-II

List – I List – II
NaBH4
(A) CH2 = CH − CHO ⎯⎯⎯ → (P) Acetal

(B) C6H5CHO + Ph − NH2 ⎯⎯
H
→ (Q) Schiff's base


(C) C6H5COCH3 + CH3 − CH2 − NH2 ⎯⎯
H
→ (R)

(D) RCHO + 2RCH2OH ⎯⎯
H
→ (S) Imine

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EXERCISE # III
Q.1 Predict the product of the reaction of propanal with each of the following :
(a) Methylmagnesium iodide, followed by dilute acid.
(b) Sodium acetylide, followed by dilute acid
(c) Phenyllithium, followed by dilute acid.
(d) Methanol containing dissolved hydrogen chloride
(e) Ethylene glycol, p-toluenesulfonic acid, benzene
(f) Aniline (C6 H5 NH2 )
(g) Dimethylamine, p-toluenesulfonic acid, benzene
(h) Hydroxylamine
(i) Hydrazine
(j) Product of part (i) heated in triethylene glycol with sodium hydroxide
(k) p-Nitrophenylhydrazine
(l) Semicarbazide
(m) Sodium cyanide with addition of sulfuric acid
(n) Chromic acid

Q.2 Give structure for the products of the reaction when butanal is treated with each of the
following reagents
(a) [Ag(NH3 )2 ]OH then HOH/H ⊕
⊖
(b) O H/HOH, Δ
(c) NH2 OH/H ⊕
(d) C6 H5 Li then HOH
⊖
(e) C6 H5 CHO, O H, Δ
(f) CH ≡ CNa then HOH/H ⊕
(g) CH2 OH − CH2 OH, H ⊕
(h) SH − CH2 − CH2 − CH2 − SH then Raney Ni/H2
(i) CH3 MgBr then H2 O
(j) HCN
(k) NaBH4

(j)

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Q.3 Column – I Column – II

(A) (P) Formation of six member ring takes place

(B) (Q) Final product is Ketone

(C) (R) Final product formed will give positive

Idoform test

(D) (S) Final product formed will react with 2,4-

DNP. (2,4-Di-nitrophenyl hydrazine)

Q.4 Arrange the following compounds in decreasing order of K eq. for hydrate formation.

(A) C6 H5 COCH3 (B)

(C) (D)

Paragraph for Q. 05 to 06
Two reactions which are example of nucleophilic attack are given as below.

Reaction-I:

Reaction-II:

Q.5 Value of x is:

(A) x ≤ 4.5 (B) x = 6 (C) x > 7 (D) Can't decide
Q.6 Value of y is:
(A) x = 4.5 (B) x = 1.5 (C) x = 7 (D) x = 9
Q.7 Some Grignard reagents react with ethyl orthoformate, followed by acidic hydrolysis, to give
aldehydes. Propose mechanisms for the two steps in this synthesis.

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Q.8 A synthesis that begins with 3,3-dimethyl-2-butanone gives the epoxide shown. Suggest
reagents appropriate for each step in the synthesis.

Q.9 Predict the organic products:

Paragraph for Q.No.10 to 11

A (Hydrocarbon )(C ⇒ 88.24%) [Molecular weight of A = 68 ]

( ii ) n −propylbromide→ B ( C8H14 )
()i Na
A ⎯⎯⎯⎯⎯⎯

→C5H6O(C )
2+
A ⎯⎯⎯Hg
⎯
dil.H2SO4

KMnO4
A ⎯⎯⎯
H+
→ Carboxylic acid + Gas

Q.10 'A' can be:

(A) H3 C − H2 C − C ≡ C − CH3 (B) CH3 − CH2 − CH2 − C ≡ C − H

(C) CH3 —CH —C  CH (D)

|
CH3

Q.11 Correct statement reagarding C is.

(A) C reacts with fehling solution to give red ppt.
(B) C gives +ve iodoform test
(C) C give -ve 2, 4, D.N.P test
(D) C is aldehyde

Q.12

'B' is:

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(A) (B)

(C) (D) CH3 − COONa

Q.13 Identify A to E:

Q.14 Show how you would accomplish the following syntheses efficiently and in good yield. You may
use any necessary reagents.
Paragraph for Q.No. 15 to 16
Identify the lettered compounds in the following reaction shceme. Compounds F, G and K are
isomers of molecular formula C13 H18 O. How could 1
H NMR spectroscopy distinguish these
three compounds from each other?

Q.15 Identify 'K' product?

(A) (B) (C) (D)

Q.16 Identify 'G' product?

(A) (B) (C) (D)

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Paragraph for Q.No. 17 to 18
In given reaction sequence

17. Alkene A is:

(A) (B) (C) (D)

18.
(A) 1 (B) 2 (C) 3 (D) 4

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EXERCISE # IV (MAINS)
Q.1 When CH2 = CH − COOH is reduced with LiAlH4 , the compound obtained will be –
[AIEEE-2003]
(A) CH3 − CH2 − CH2 OH (B) CH3 − CH2 − CHO
(C) CH3 − CH2 − COOH (D) CH2 = CH − CH2 OH
Q.2 Which one of the following undergoes reaction with 50% sodium hydroxide solution to give the
corresponding alcohol and acid ? [AIEEE-2004]
(A) Phenol (B) Benzaldehyde (C) Butanal (D) Benzoic acid
Q.3 Which one of the following is reduced with Zn − Hg/HCl to give the corresponding hydrocarbon
[AIEEE-2004]
(A) Butan-2-one (B) Acetic acid (C) Acetamide (D) Ethyl acetate
Q.4 On mixing ethyl acetate with aqueous sodium chloride, the composition of the resultant
solution is [AIEEE-2004]
(A) CH3 COOC2 H5 + NaCl (B) CH3 COONa + C2 H5 OH
(C) CH3 COCl + C2 H5 OH + NaOH (D) CH3 Cl + C2 H5 COONa
Q.5 The best reagent to convert pent-3-en-2-ol into pent -3 -en −2 − one is - [AIEEE-2005]
(A) Acidic dichromate (B) Acidic permanganate
(C) Pyridinium chloro-chromate (D) Chromic anhydride in glacial acetic acid
Q.6 Rate of the reaction-

is fastest when X is -
(A) NH2 (B) Cl (C) OCOR (D) OC2 H5
Q.7 Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH
is- [AIEEE-2006]
(A) CH3 CH2 CH(OH)CH2 CH3 (B) C6 H5 CH2 CH2 OH

(C) (D) PhCHOHCH3

P+ I2 H2O
Q.8 In the following sequence of reactions CH3CH2OH ⎯⎯→ A ⎯⎯⎯
Mg
Ether
→ B ⎯⎯⎯
HCHO
→C ⎯⎯ → D then

compound 'D' is – [AIEEE-2007]

(A) Butanal (B) n-Butyl alcohol (C) n-Propyl alcohol (D) Propanal
Q.9 In the following sequence of reactions, the alkene affords the compound 'B' :- [AIEEE-2008]
O3 H2O
CH3CH = CHCH3 ⎯⎯ → A ⎯⎯
Zn
→B
The compound B is
(A) CH3 CH2 CHO (B) CH3 COCH3 (C) CH3 CH2 COCH3 (D) CH3 CHO
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Q.10 Bakelite is obtained from phenol by reacting with [AIEEE-2008]
(A) (CH2 OH)2 (B) CH3 CHO (C) CH3 COCH3 (D) HCHO
Q.11 Which of the following on heating with aqueous KOH, produces acetaldehyde ? [AIEEE-2009]
(A) CH2 ClCH2 Cl (B) CH3 CHCl2 (C) CH3 COCl (D) CH3 CH2 Cl
Q.12 In Cannizzaro reaction given below :- [AIEEE-2009]


2PhCHO ⎯⎯
:OH
→ PhCH2OH + PhCO2
the slowest step is :-
(A) The abstraction of proton from the carboxylic group
(B) The deprotonation of PhCH2 OH
⊖
(C) The attack of : OH at the carboxyl group
(D) The transfer of hydride to the carbonyl group
Q.13 One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a
molecular mass of 44u. The alkene is :- [AIEEE-2010]
(A) Ethene (B) Propene (C) 1-Butene (D) 2-Butene
Q.14 Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms
the presence of :- [AIEEE-2011]
(A) An isopropyl group (B) An acetylenic triple bond
(C) Two ethylenic double bonds (D) A vinyl grou
Q.15 Ozonolysis of an organic compound 'A' produces acetone and propionaldehyde in equimolar
mixture. Identify 'A' from the following compounds : - [AIEEE-2011]
(A) 2-Methyl - 1- pentene (B) 1-Pentene
(C) 2-Pentene (D) 2-Methyl-2-pentene
Q.16 Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of
the products contains sodium trichloroacetate and another compound. The other compound is:
[AIEEE-2011]
(A) 2,2,2-Trichloropropanol (B) Chloroform
(C) 2,2,2-Trichloroethanol (D) Trichloromethanol
Q.17 Silver Mirror test is given by which one of the following compounds? [AIEEE-2011]
(A) Formaldehyde (B) Benzophenone (C) Acetaldehyde (D) Acetone
Q.18 In the given transformation, which of the following is the most appropriate reagent ?
[AIEEE-2012]

⊖
(A) NaBH4 (B) NH2 NH2 , O H (C) Zn − Hg/HCl (D) Na, Liq. NH3

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Q.19 Iodoform can be prepared from all except :- [AIEEE-2012]
(A) Isobutyl alcohol (B) Ethyl methyl ketone
(C) Isopropyl alcohol (D) 3-Methyl-2-butanone
Q.20 A compound with molecular mass 180 is acylated with CH3 COCl to get a compound with
molecular mass 390. The number of amino groups present per molecule of the former
compound is :- [JEE(Main)-2013]
(A) 2 (B) 5 (C) 4 (D) 6
Q.21 The major organic compound formed by the reaction of 1,1,1-trichloroethane with silver
powder is :- [JEE(Main)-2014]
(A) 2-Butyne (B) 2-Butene (C) Acetylene (D) Ethene
Q.22 The most suitable reagent for the conversion of R − CH2 − OH → R − CHO is :-
[JEE(Main)-2014]
(A) CrO3 (B) PCC (Pyridinium chlorochromate)
(C) KMNO4 (D) K 2 Cr2 O7
Q.23 A compound A with molecular formula C10 H13 Cl gives a white precipitate on adding silver
nitrate solution. A on reacting with alcoholic KOH gives compound B as the main product. B on
ozonolysis gives C and D. C gives Cannizaro reaction but not aldol condensation. D gives aldol
condensation but not Cannizaro reaction. A is : [JEE(Main)-2015]

(A) (B)

(C) C6H5 − CH2 − CH2 − CH2 − CH2 − Cl (D) C6H5 − CH2 − CH2 − CH − CH3
|
Cl
Q.24 In the reaction sequence [JEE(Main)-2015]

the product B is:-

(A) CH3 − CH = CH − CHO (B) CH3 − CH2 − CH2 − CH3

(C) CH3 − CH2 − CH2 − CH2 − OH (D)

Q.25 Which compound would give 5-keto-2-methyl hexanal upon ozonolysis?
[JEE(Main) 2015]

(A) (B) (C) (D)

APNI KAKSHA 23
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.26 The correct sequence of reagents for the following conversion will be: [JEE(Main) 2017]

(A) CH3 MgBr, [Ag(NH3 )2 ]+ OH − , H + /CH3 OH

(B) [Ag(NH3 )2 ]+ OH − , CH3 MgBr, H + /CH3 OH
(C) [Ag(NH3 )2 ]+ OH − , H + /CH3 OH, CH3 MgBr
(D) CH3 MgBr, H + /CH3 OH, [Ag(NH3 )2 ]+ OH −
Q.27 The major product formed in the following reaction is: [JEE MAIN-2019]

(A) (B)

(C) (D)
Q.28 In the following reaction [JEE MAIN-2019]
Aldehyde + alcohol ⎯⎯ → Acetal
HCl

Aldehyde Alcohol
HCHO tBuOH

CH3CHO MeOH
The best combinations is :
(A) CH3 CHO and t BuOH (B) HCHO and t BuOH
(C) CH3 CHO and MeOH (D) HCHO and MeOH

Q.29 cannot be prepared by : [JEE MAIN-2019]

(A) PhCOCH3 + CH3 CH2 MgX (B) PhCOCH2 CH3 + CH3 MgX
(C) HCHO + PhCH(CH3 )CH2 MgX (D) CH3 CH2 COCH3 + PhMgX
APNI KAKSHA 24
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.30 In the following reactions, products A and B are: [JEE MAIN-2019]

(A)

(B)

(C)

(D)

Q.31 The increasing order of the reactivity of the following with LiAlH4 is: [JEE MAIN-2019]

(A) (A) < (B) < (C) < (D) (B) (A) < (B) < (D) < (C)
(C) (B) < (A) < (C) < (D) (D) (B) < (A) < (D) < (C)
Q.32 The aldehydes which will not form Grignard product with one equivalent Grignard reagents
are: [JEE MAIN-2019]

(A) (B), (C) (B) (B), (C), (D) (C) (C), (D) (D) (B), (D)

APNI KAKSHA 25
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.33 Major products of the following reaction are: [JEE MAIN-2019]

(A) (B) CH3 OH and HCO2 H

(C) (D)

Q.34 But-2-ene on reaction with alkaline KMnO4 at elevated temperature followed by acidification
will give: [JEE MAIN-2019]
(A) one molecule of CH3 CHHOO and one molecule of CH3 COOH
(B) 2 molecules of CH3 CHO
(C) 2 molecules of CH3 COOH
(D) CH3 − CH − CH − CH3
| |
OH OH
Q.35 An organic compound neither reacts with neutral ferric chloride solution moor with Fehling
solution. It however, reacts with Grignard reagent and gives positive iodoform test. The
compound is : [JEE MAIN-2019]

(A) (B)

(C) (D)

Q.36 The major product of the following reaction is : [JEE MAIN-2019]

(A) (B) (C) (D)

APNI KAKSHA 26
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.37 The major product obtained in the following reaction is : [JEE MAIN-2019]

(A) (B) (C) (D)

HCl
Q.38 In the following reaction carbonyl compound +MeOH ⇌ acetal. Rate of the reaction is the
highest for : [JEE MAIN-2019]

(A) Acetone as substrate and methanol in excess

(B) Acetone as substrate and methanol in stoichiometric amount

(C) Propanal as substrate and methanol in excess

(D) Propanal as substrate and methanol in stoichiometric amount.

( ) ( ) 3
1 NaBH ( ) ( ) 2
2 PBr ( )
3 Mg/Ether 4 CO 5 H
Q.39 Hex-3-ynal ⎯⎯⎯⎯ 4
→⎯⎯⎯ →⎯⎯⎯⎯ →⎯⎯⎯ →⎯⎯⎯ → (X), formed product X will be:
[JEE MAIN 2020]

(A) (B)

(C) (D)

Q.40

What will be the major product? [JEE MAIN 2020]

(A) (B)

(C) (D)

APNI KAKSHA 27
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

Q.41

Predict the compound (P) on the basis of above sequence of the reactions? [JEE MAIN 2020]

(A) (B)

(C) (D)

Q.42 The increasing order of the following compounds towards HCN addition is
[JEE MAIN 2020]

(i) (ii)

(iii) (iv)

(A) (iii) < (iv ) < (ii ) < ( i ) (B) (iii) < (i) < (iv) < (ii)
(C) (iii) < (iv ) < (i) < (ii) (D) (i) < (iii) < (iv) < (ii)
Q.43 The increasing order of the reactivity of the following compounds in nucleophilic addition
reaction is Propanal, Benzaldehyde, Propanone, Butanone [JEE MAIN 2020]
(A) Propanal < Propanone < Butanone < Benzaldehyde
(B) Benzaldehyde < Propanal < Propanone < Butanone
(C) Benzaldehyde < Butanone < Propanone < Propanal
(D) Butanone < Propanone < Benzaldehyde < Propanal

Q.44 The compound A in the following reactions is [JEE MAIN 2020]

( i) CH3MgBr/H2O ( i ) O3
A. ⎯⎯⎯⎯⎯⎯
→
( ii) Conc.H2SO4 / B. ⎯⎯⎯⎯
→C + D
( ii) Zn/H2O

C.

D.

(A) (B)

(C) (D)

APNI KAKSHA 28
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.45 Consider the following reactions [JEE MAIN 2020]
'A' ⎯⎯⎯⎯
ozonolysis
→ 'B'+ 'C'
(C6H14 )

(A) (B)

(C) (D)

Q.46 Given below are two statements : [JEE MAIN 2021]

Statement I : The nucleophilic addition of sodium hydrogen sulphite to an aldehyde or a ketone
involves proton transfer to form a stable ion.
Statement II : The nucleophilic addition of hydrogen cyanide to an aldehyde or a ketone yields
amine as final product.
In the light of the above statements, choose the most appropriate answer from the options given
below :
(A) Both Statement I and Statement II are true.
(B) Statement I is true but Statement II is false.
(C) Statement I is false but Statement II is true.
(D) Both Statement I and Statement II are false.
Q.47 For the reaction given below : [JEE MAIN 2021]

The compound which is not formed as a product in the reaction is a :

(A) compound with both alcohol and acid functional groups
(B) monocarboxylic acid
(C) dicarboxylic acid
(D) diol

APNI KAKSHA 29
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.48 The structures of A and B formed in the following reaction are: [JEE MAIN 2021]
[Ph = −C6 H5 ]

(A) (B)

(C) (D)

Q.49 The structure of the starting compound P used in the reaction given below is: [JEE MAIN 2021]

(A) (B) (C) (D)

Q.50

Which among the above compound/s does/do not form Silver mirror when treated with
Tollen's reagent? [JEE MAIN 2021]
(1) (I), (III) and (IV) only (2) Only (IV)
(3) Only (II) (4) (III) and (IV) only

APNI KAKSHA 30
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.51 The major product (P) in the following reaction is : [JEE MAIN 2021]

(A) (B) (C) (D)

Q.52 [JEE MAIN 2021]

In the above chemical reaction, intermediate " X " and reagent/condition " A " are:

(A) (B)

(C) (D)

Q.53 Which of the following is least basic? [JEE MAIN 2021]

(A) (CH3 CO)N̈HC2 Hs (B) (C2 H5 )3 N̈
¨
(C) (CH3 CO)2 NH (D) (C2 H5 )2 N̈ H
Q.54 Hoffmann bromomide degradation of benzamide gives product A, which upon heating with
CHCl3 and NaOH gives product B. The structures of A and B are : [JEE MAIN 2021]

(A) (B)

(C) (D)

APNI KAKSHA 31
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.55 Primary, secondary and tertiary amines can be separated using :- [JEE MAIN 2021]
(A) Para-Toluene sulphonyl chloride (B) Chloroform and KOH
(C) Benzene sulphonic acid (D) Acetyl amide
Q.56 C7 H7 N2 OCl + C2 H3 OH → [O + N2 + X + ′′ Y ′′
′′ ′′

(A) In the above reaction, the structural formula of [JEE MAIN 2021]

(A) (B)

(C) (D)

Q.57

Considering the above reaction, X and Y respectively are [JEE MAIN 2021]

(A)

(B)

(C)

(D)

APNI KAKSHA 32
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

Q.58

Consider the above chemical reaction and identify product "A" [JEE MAIN 2021]

(A) (B)

(C) (D)

Q.59 In the reaction of hypobromite with amide, the carbonyl carbon is lost as : [JEE MAIN 2021]
(1) CO2−
3 (2) HCO−
3 (3) CO2 (4) CO
Q.60 Which of the following is an example of Conjugated diketone? [JEE MAIN 2022]

(A) (B)

(C) (D)

Q.61

Consider the above reaction sequence and identify the product B. [JEE MAIN 2022]

(A) (B) (C) (D)

Q.62 Which will have the highest enol content? [JEE MAIN 2022]

(A) (B) (C) (D)

APNI KAKSHA 33
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.63 The correct structure of product ' A ' formed in the following reaction. [JEE MAIN 2022]

(A) (B) (C) (D)

Q.64 ' R ' formed in the following sequence of reaction is: [JEE MAIN 2023]

(A) (B)

(C) (D)

Q.65 Number of compounds giving (i) red colouration with ceric ammonium nitrate and also (ii)
positive iodoform test from the following is _______. [JEE MAIN 2023]

APNI KAKSHA 34
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.66 [JEE MAIN 2023]
List-I List-II
(Reaction) (Reagents)
(A) Hoffmann Degradation (I) Conc. KOH,
(B) Clemenson reduction (II) CHCl3,NaOH/H3O+
(C) Cannizaro reaction (III) Br2, NaOH
(D) Reimer-Tiemann (IV) Zn-Hg/HCl
reaction
(A) (A) − III, (B) − IV, (C) − II, (D) − I
(B) (A) − II, (B) − IV, (C) − I, (D) − III
(C) (A) − III, (B) − IV, (C) − I, (D) − II
(D) (A) − II, (B) − I, (C) − III, (D) − IV
Q.67 Which of the following compounds would give the following set of qualitative analysis ?
[JEE MAIN 2023]
(i) Fehling's Test : Positive
(ii) Na fusion extract upon treatment with sodium nitroprusside gives a blood red colour but
not

(A) (B)

(C) (D)

Q.68 Cyclohexylamine when treated with nitrous acid yields (P). On treating (P) with PCC results in
(Q). When (Q) is heated with dil. NaOH we get (R) The final product (R) is : [JEE MAIN 2023]

(A) (B)

(C) (D)

APNI KAKSHA 35
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.69 The structures of major products A, B and C in the following reaction are sequence.
[JEE MAIN 2023]

(A) (B)

(C) (D)

APNI KAKSHA 36
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
EXERCISE-IV # (A) (OBJECTIVE QUESTIONS)
Q.1 The formation of cyanohydrin from a ketone is an example of: [IIT 1990]
(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution
Q.2 The enolic form of acetone contains: [IIT 1990]
(A) 9 sigma bonds, 1 pi bond and 2 lone pairs
(B) 8 sigma bonds, 2 pi bonds and 2 lone pairs
(C) 10 sigma bonds, 1 pi bond and 1 lone pair
(D) 9 sigma bonds, 2 pi bonds and 1 lone pair
Q.3 m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives:
[IIT 1991]
(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(B) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl and m-hydroxybenzyl alcohol
(D) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
Q.4 Hydrogenation of benzoyl chloride in the presence of Pdd and BaSO4 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
Q.5 An organic compound C3 H6 O does not give a precipitate with 2,4-Dinitrophenyl hydrazine
reagent and does not react with metallic sodium. It could be: [IIT 1993]
(A) CH3 CH2 CHO (B) CH3 COCH3
(C) CH2 = CH − CH2 OH (D) CH2 = CH − O − CH3
Q.6 Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
[IIT 1995]
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane

Q.7 In the Cannizzaro reaction given below, 2Ph − CHO 2 the slowest
Ph − CH2 OH + PhCO−
step is: [IIT 1996]
(A) The attack of OH − at the carbonyl group
(B) The transfer of hydride to the carbonyl group
(C) The abstraction of proton from the carboxylic acid
(D) The deprotonation of Ph − CH2 OH
Q.8 Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group
is : [IIT 1997]
(A) MeCOCl (B) MeCHO (C) MeCOOMe (D) MeCOOCOMe
APNI KAKSHA 37
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.9 In a Cannizzaro reaction the intermediate which is the best hydride donor is: [IIT 1997]

(A) (B)

(C) (D)
Q.10 CH3 CHO + H2 NOH ⟶ CH3 − CH = N − OH. The above reaction occurs at: [IIT 1997]
(A) pH = 1 (B) pH = 4.5 (C) Any value of pH (D) pH = 12
Q.11 Among the following compounds, which will react acetone to give a product containing
>C=N− [IIT 1998]
(A) C6 H5 NH2 (B) (CH3 )3 N (C) C6 H5 NHC6 H5 (D) C6 H5 NHNH2
Q.12 The product obtained via oxymercuration (HgSO4 − H2 SO4 ) of 1-butyne would be
[IIT 1998]

(A) (B) CH3 CH2 CH2 CHO

(C) CH3 CH2 CHO + HCHO (D) CH3 CH2 COOH + HCOOH
Q.13 Which of the following will undergo aldol condensation: [IIT 1998]
(A) Acetaldehyde (B) Propanaldehyde
(C) Benzaldehyde (D) Trideutero acetaldehyde
Q.14 Which of the following will react with water: [IIT 1998]
(A) CHCl3 (B) Cl3 CCHO (C) CCl4 (D) ClCH2 CH2 Cl
Q.15 A new carbon-carbon bond formation is possible in [IIT 1998]
(A) Cannizzaro reaction (B) Friedel-Crafts alkylation
(C) Clemmensen reduction (D) Reimer-Tiemann reaction
Q.16 Which of the following has the most acidic hydrogen: [IIT 2000]
(A) 3-hexanone (B) 2,4-hexanedione
(C) 2,5-hexanedione (D) 2,3-hexandione
Q.17 A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
[IIT 2001]
(A) benzyl alcohol and sodium format
(B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium format
(D) benzyl alcohol and methyl alcohol
APNI KAKSHA 38
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.18 1-propanol & 2-propanol can be best distinguished by : [IIT 2001]
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acidic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2 SO4 followed by reaction with Fehling solution
Q.19 Compound A (molecular formula C3 H8 O ) is treated with acidified potassium dichromate to
form a product B (molecular formula C3 H6 O ). B forms a shining silver mirror on warming with
ammonical silver nitrate. B when treated with an aqueous solution of H2 NCONHNH2 . HCl and
sodium acetate gives a product C. Identify the structure of C. [IIT 2002]
(A) CH3 CH2 CH = NNHCONH2 (B)

(C) (D) CH3 CH2 CH = NCONHNH2

Q.20

any one of the products formed is :

(A) (B)

(C) (C)

Q.21 Products formed by P & Q can be differentiated by:

[IIT 2003]
(A) 2, 4 DNP (B) Lucas reagent (ZnCl2 ) conc. HCl
(C) NaHSO3 (D) Fehlings solution

APNI KAKSHA 39
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.22 The order of reactivity of phenyl Magnesium Bromide with the following compounds is
[IIT 2004]

(A) II > III > I (B) I > III > II

(C) II > I > III (D) All react with the same rate

Q.23 [IIT 2004]

What is X ?
(A) CH3 COOH (B) BrCH2 , COOH (C) (CH3 CO)2 O (D) CHO − COOH
Q.24 The smallest ketone and its next homologue are reacted with NH2 OH to form oxime.
[IIT 2006]
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active
Q.25 Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E.
Compound E on further treatment with aqueous KOH yields compound F. Compound F is
[IIT 2007]

(A) (B) (C) (D)

Q.26 Statement-1 : Glucose gives a reddish-brown precipitate with Fehling's solution.

because
Statement-2 : Reaction of glucose with Fehling's solution gives CuO and gluconic acid.
[IIT 2007]
(A) Statement- 1 is True, Statement- 2 is True; Statement- 2 is a correct explanation for
Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement- 2 is True.

APNI KAKSHA 40
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.27 Match the compounds/ion in column I with their properties/ reaction in Column II. Indicate
your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
[IIT 2007]
Column I Column II
(A) C6 H5 CHO (P) gives precipitate with 2,4-dinitrophenylhydrazine
(B) CH3 C ≡ CH (Q) gives precipitate with AgNO3
(C) CN − (R) is a nucleophile
(D) I − (S) is involved in cyanohydrin formation

Paragraph for Question No. 28 to 30

A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to
compounds J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound
L, whereas K on reaction with KOH gives only M.

Q.28 Compound H is formed by the reaction of [IIT 2008]

(A) (B)

(C) (D)

Q.29 The structure of compound 𝐈 is [IIT 2008]

(A) (B) (C) (D)

Q.30 The structures of compounds J, K and L, respectively, are [IIT 2008]

(A) PhCOCH3 , PhCH2 COCH3 and PhCH2 COO− K +
(B) PhCHO, PhCH2 CHO and PhCOO− K +
(C) PhCOCH3 , PhCH2 CHO and CH3 COO− K +
(D) PhCHO, PhCOCH3 and PhCOO− K +

APNI KAKSHA 41
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Paragraph for Question Nos. 31 to 33
A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr
followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R,
which undergoes intramolecular aldol reaction to give predominantly S.

1.MeMgBr 1.O 1.OH−→ s

P ⎯⎯⎯⎯⎯→ Q ⎯⎯⎯⎯⎯3 → R ⎯⎯⎯⎯
2.H+ ,H O 2.Zn,H O
2
2.
2
3.H SO ,
2 4
Q.31 The structure of the carbonyl compound P is [IIT 2009]

(A) (B) (C) (D)

Q.32 The structure of the products Q and R, respectively, are [IIT 2009]

(A) (B)

, ,

(C) (D)

, ,
Q.33 The structure of the product 𝐒 is [IIT 2009]

(A) (B)

(C) (D)

APNI KAKSHA 42
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Paragraph for Questions Nos. 34 to 35
An acyclic hydrocarbon P, having molecular formula C6 H10, gave acetone as the only organic
product through the following sequence of reactions, in the which Q is an intermediate organic
compound.

Q.34 The structure of compound P is - [IIT 2011]

(A) CH3 CH2 CH2 CH2 − C ≡ C − H (B) H3 CH2 C ≡ C − CH2 CH3

(C) (D)

Q.35 The structure of the compound Q is - [IIT 2011]

(A) (B)

(C) (D)

Q.36 The number of aldol reaction(s) that occurs in the given transformation is [IIT 2012]

(A) 1 (B) 2 (C) 3 (D) 4

Q.37 Among P, Q, R and S, the aromatic compound(s) is / are : [IIT 2013]

(A) P (B) Q (C) R (D) S

APNI KAKSHA 43
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.38 After completion of the reactions (I and II), the organic compound(s) in the reaction mixtures
is(are) [IIT 2013]

(A) Reaction I: P and Reaction II : P

(B) Reaction I : U, acetone and Reaction II : Q acetone
(C) Reaction I : T, U, acetone and Reaction II : P
(D) Reaction I : R, acetone and Reaction II : S acetone
Q.39 The major product in the following reaction is [IIT 2014]

(A) (B)

(C) (D)

Q.40 The major product of the following reaction is - [IIT 2015]

(A) (B)

(C) (D)

APNI KAKSHA 44
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.41 In the following reactions, the product S is - [IIT 2015]

(A) (B)

(C) (D)
Q.42 Positive Tollen's test is observed for: [IIT 2016]

(A) (B) (C) (D)

Q.43 The major product of the following reaction sequence is : [IIT 2016]

(A) (B)

(C) (D)
Q.44 Compound P and R upon ozonolysis produce Q and S, respectively. The molecular formula of Q
and S is C8 H8 O. Q undergoes Cannizzaro reaction but not haloform reaction, where S undergoes
haloform reaction but not Cannizzaro reaction. [IIT JEE 2017]

The option(s) with suitable combination of P and R, respectively, is (are)

APNI KAKSHA 45
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

(A)

(B)

(C)

(D)

Q.45 The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are) [IIT JEE 2018]

(A) (B)

(C) (D)

Q.46 The desired product X can be prepared by reacting the major product of the reactions in LIST-I
with one or more appropriate reagents in LIST-II.
(given, order of migratory aptitude: aryl > alkyl > hydrogen) [IIT JEE 2018]

APNI KAKSHA 46
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
List-I List-II

P. 1. I2 , NaOH

Q. 2. [Ag(NH3 )2 ]OH

R. 3. Fehling solution

S. 4. HCHO, NaOH

5. NaOBr
The correct option is
(A) P → 1; Q → 2,3; R → 1,4; S → 2,4 (B) P → 1,5; Q → 3,4; R → 4,5; S → 3
(C) P → 1,5; Q → 3,4; R → 5; S → 2,4 (D) P → 1,5; Q → 2,3; R → 1,5; S → 2,3

Q.47 Choose the correct option(s) for the following set of reactions [IIT JEE 2019]

(A) (B)

(C) (D)

APNI KAKSHA 47
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
Q.48 In the reaction scheme shown below, Q, R, and S are the major products. [IIT JEE 2020]

The correct structure of

Q.49 Correct option(s) for the following sequence of reactions is(are)

(A) Q = KNO2, W = LiAlH4 (B) R = benzenamine, V = KCN

(C) Q = AgNO2, R = phenylmethanamine (D) W = LiAlH4, V = AgCN
APNI KAKSHA 48
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

Q.50 In the following reactions, P, Q, R and S are the major products.

The correct statement(s) about 𝐏, 𝐐, 𝐑, and 𝐒 is(are)

(A) Both 𝐏 and 𝐐 have asymmetric carbon(s).
(B) Both 𝐐 and 𝐑 have asymmetric carbon(s).
(C) Both 𝐏 and 𝐑 have asymmetric carbon(s).
(D) 𝐏 has asymmetric carbon(s), 𝐒 does not have any asymmetric carbon.

APNI KAKSHA 49
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
EXERCISE-IV # (B) (SUBJECTIVE QUESTIONS)
Q.1 NaOC2H5 inabsolute
C6H5 − CHO + CH3 − COOC2H5 ⎯⎯⎯⎯⎯⎯
C2H5OHandheat
→(D) [IIT 1995]

Q.2 [IIT 1996]

Q.3 Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric
oximes. Write structures of the oximes. [IIT 1997]
Q.4 An aldehyde (A) (C11 H8 O), which does not undergo self aldol condensation, gives benzaldehyde
and two mole of (B) on ozonolysis. Compound (B), on oxidation with silver ion, gives oxalic acid.
Identify the compounds (A) and (B). [IIT 1998]

Q.5 [IIT 1998]

Q.6 What would be the major product in each of the following reaction? [IIT 2000]

Q.7 Identify (A), (B) and (C), and give their structures. [IIT 2000]

Q.8 Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8 H8 O2

were given for identification. Based on the following observations, give structure of the
compounds. [IIT 2002]
(i) Both A and B form a silver mirror with Tollen's reagent; also, B gives a positive test with
FeCl3 solution.
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution.
(iv) E on acid hydrolysis gives 1,4-dihydroxybenzene.
Q.9

( A ) ⎯⎯⎯⎯
ozonolysis
→( F ) + (G ) ⎯⎯⎯
NaOH
→HCOONa + 1ºalcohol
(D) is isomer of A. E gives negative test with Fehling solution but gives iodoform test F and G
gives Tollen's test but do not give iodoform test. Identify A to G. [IIT 2003]

APNI KAKSHA 50
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
ANSWER KEY
EXERCISE # I
1. (A) 2. (B) 3. (C) 4. (D) 5. (C) 6. (B) 7. (C)
8. (C) 9. (D) 10. (C) 11. (A) 12. (C) 13. (C) 14. (C)
15. (C) 16. (D) 17. (A) 18. (C) 19. (D) 20. (C) 21. (C)
22. (B) 23. (D) 24. (B) 25. (C) 26. (D) 27. (B) 28. (A)
29. (B) 30. (C) 31. (D) 32. (D) 33. (B) 34. (C) 35. (C)
36. (D) 37. (B) 38. (C) 39. (B) 40. (A) 41. (D) 42. (C)
43. (D) 44. (B) 45. (B) 46. (C) 47. (A) 48. (C) 49. (C)
50. (D)
EXERCISE # II
1 (A,B) 2 (C,D) 3 (A,B,C)4 (A,B,C) 5 (B,C) 6 (A,B)
7 (A,B,C,D) 8 (A,B,C) 9 (A,C,D) 10 (B,C,D) 11 (A,D) 12 (D)
13 (C) 14 (C) 15 (D) 16 (B) 17 (B) 18 (C)
19 (B) 20 (B) 21 (A,B,C)22 (A) → P, (B) → Q, (C) → S, (D) → R
23 (A) R, (B) Q,S, (C) S, (D) P
EXERCISE # III

1. (a) (b)

(c) (d)

(e) (f) CH3 − CH2 − CH = NH − Ph

(g) (h) CH3 − CH2 − CH = N − OH

(i) CH3 − CH2 − CH = N − NH2 (j) CH3 − CH2 − CH2
(k) p-Nitro phenyl hydrazon (l) Semi carbazone

(m) (n) CH3 − CH2 − CO2 H

Q.2 (a) (b)

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(ORGANIC CHEMISTRY) CARBONYL COMPOUND

(c) C − C − C − C = N − OH (d)

(e) (f)

(g) (h) C − C − C − C

(i) 2∘ alcohol (j) Cyanohydrine (k) 1∘ alcohol

(l)

Q.3 Ans. (A)P,Q,S;(B)P,Q,S;(C)P,Q,S;(D)P,Q,S

Q.4 Ans. 3 > 2 > 1 > 4 Q.5 Ans.(C) Q.6 Ans. (A)

Q.7 Ans.
Q.8 Ans. H + /Br2 ; H2 /Ni; NaOH

Q.9 Ans. (a) (b)

(c)

Q.10 Ans. (B,C) Q.11 Ans. (B) Q.12 Ans. (B) Q.13
Q.14

(d) (i) H2 , Ni (e) NH2 NH2 /H2 O2 (f) NaBH4

Q.15 Ans. (A) Q.16 Ans. (D) Q 17. Ans. (B) Q.18 Ans. (D)

APNI KAKSHA 52
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
EXERCISE # IV (MAINS)
1. (4) 2. (2) 3. (1) 4. (2) 5. (4) 6. (2) 7. (4)
8. (3) 9. (4) 10. (4) 11. (2) 12. (4) 13. (4) 14. (4)
15. (4) 16. (3) 17. (1, 3) 18. (2) 19. (1) 20. (2) 21. (1)
22. (2) 23. (2) 24. (1) 25. (4) 26. (3) 27. (2) 28. (4)
29. (3) 30. (1) 31. (2) 32. (4) 33. (3) 34. (3) 35. (1)
36. (3) 37. (3) 38. (3) 39. (A) 40. (A) 41. (B) 42. (B)
43. (D) 44. (C) 45. (B) 46. (B) 47. (A) 48. (A) 49. (A)
50. (C) 51. (B) 52. (C) 53. (C) 54. (B) 55. (A) 56. (A)
57. (B) 58. (C) 59. (A) 60. (C) 61. (A) 62. (C) 63. (A)
64. (B) 65. (C) 66. (C) 67. (D) 68. (B) 69. (D)

EXERCISE # IV - A (OBJECTIVE QUESTIONS)

1 (B) 2 (A) 3 (D) 4 (B) 5 (D) 6 (D) 7 (B)
8 (A) 9 (D) 10 (B) 11 (A,D) 12 (A) 13 (A,B,D) 14 (B)
15 (B,D) 16 (B) 17 (A) 18 (C) 19 (A) 20 (C) 21 (D)
22 (C) 23 (C) 24 (B) 25 (A) 26 (C)
27 (A) P,S; (B) Q; (C) Q,R,S; (D) Q,R 28 (B) 29 (A) 30 (D) 31 (B)
32 (A) 33 (B) 34 (D) 35 (B) 36 (C) 37 (A,B,C,D) 38. (C)
39 (D) 40 (A) 41 (A) 42 (A,B,C) 43. (A) 44 (A, B) 45 (A, B,D)
46. (D) 47. (A,B) 48. (B, D) 49. (C,D) 50. (C,D)

49.
Therefore, correct options are
Q = AgNO2, R = phenylmethanamine
W = LiAlH4, V = AgCN

APNI KAKSHA 53
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
EXERCISE - IV # B (SUBJECTIVE QUESTIONS)
1. C6 H5 CH = CHCOOC2 H5 , CH3 − CH = CH − COOC2 H5

2.
3.

4.

5. 6.

7.

8.

9.

APNI KAKSHA 54
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
SOLUTION
EXERCISE (JEE-MAIN)
39.

40.

41.

42. Attack of nucleophile on carbonyl centre depends upon

(i) Steric factor (ii) Electronic factor
∴ Rate of reaction should follow the order
(ii) > (iv ) > (i) > (iii)
43. Increasing hindrence and electron relasing group (ERG) attached on carboxyl group decrease
the reactivity.
Correct order of nucleophilic addition reaction is

APNI KAKSHA 55
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

44.

45.

46. Statement I : Correct

Statement II :

APNI KAKSHA 56
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
47.

48.

49.

NaOCl is used in haloform reaction as reagent.

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(ORGANIC CHEMISTRY) CARBONYL COMPOUND
50. Aldehydes gives positive Tollen’s test (silver mirror)

51.

52.

53. For the given compounds:

(a)
; L.P. on Nitrogen is delocalised.

(b)

; L.P. on Nitrogen is delocalised.

(c)

; L.P. on Nitrogen is delocalised due to conjugation with both

(Hence least basic)

(d) CH3 − CH2 − N̈H − CH2 − CH3 ; L.P. on Nitrogen is localised.

APNI KAKSHA 58
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

54.

55. Primary amines react with Para Toluene sulfonyl chloride to form a precipitate that is soluble
in NaOH.Secondary amines reacts with para toluene sulfonyl chloride to give a precipitate that
is insoluble in NaOH. Tertiary amines do not react with para toluen.

56.

57.

APNI KAKSHA 59
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

58.

59.

60. is a conjugated diketone

61. Although Acetyl Acetone predominantly gives Acid base reaction with G.R due to Active
methylene group but according to given option ans should be based on nucleophilic addition
reaction (NAR).

APNI KAKSHA 60
(ORGANIC CHEMISTRY) CARBONYL COMPOUND

62.

, Which is aromatic in nature.

63. PhCH = O + PhCH = O

PhCH2 OD + PhCO−
2

64.

65.

66. Reactions Reagent used

(A) Hoffmann degradation Br2 /NaOH
(B) Clemenson reduction Zn − Hg/HCl
(C) Cannizaro reaction conc. KOH/Δ
(D) Reimer-Tiemann reaction CHCl3 , NaOH/H3 O+

APNI KAKSHA 61
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
67. Aromatic aldehydes do not give Fehling's test.. Both nitrogen and sulfur must be present to
obtain blood red colour Sodium nitroprusside gives blood red colour with S & N.
68.

69.

APNI KAKSHA 62
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
REDUCTION SUMMARY
Name Reagent Function
Wolf Kishner Reduction (i) 𝐍𝟐 𝐇𝟒 / (ii) 𝐊𝐎𝐇, 𝚫

Clemenson Reduction 𝐙𝐧 − 𝐇𝐠/𝐇𝐂𝐥

Mozingo Reduction
Dry HCl followed by
Raney Ni
Stephen's Reduction 𝐒𝐧𝐂𝐥𝟐 /𝐇𝐂𝐥 followed by 𝐑 − 𝐂 ≡ 𝐍 ⟶ 𝐑 − 𝐂𝐇 = 𝐎
𝐇𝟑 𝐎 +
MPV Reduction

Hydroboration Reduction (i) 𝐁𝟐 𝐇𝟔 (ii) 𝐀𝐜𝐎𝐇, 𝐇𝟐 𝐎

Bouvoult Blank Reduction 𝐍𝐚 in 𝐄𝐭𝐎𝐇 𝐑 − 𝐂𝐎𝐎 − 𝐑 → 𝐑𝐂𝐇𝟐 𝐎𝐇

+ 𝐑𝐎𝐇
Transfer Hydrogenation 𝐍𝟐 𝐇𝟒 /𝐇𝟐 𝐎𝟐

Rosenmund Reduction 𝐇𝟐 , 𝐏𝐝 − 𝐁𝐚𝐒𝐎𝟒

Birch Reduction 𝐍𝐚 in Liq. 𝐍𝐇𝟑

Red phosphorus in presence of HI Red 𝐏 + 𝐇𝐈

APNI KAKSHA 1
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
OXIDATION
1. OXIDATION
1.1 Introduction
(i) oxidation is defined as the addition of oxygen (electronegative) element to a substance or
removal of hydrogen (electropositive) element from a substance.
or
Oxidation of an organic molecule usually corresponds to increasing its oxygen content or
decreasing its hydrogen content.

(ii) Oxidation of an organic compound may be more broadly defined as a reaction that increases its
content of any element more electronegative than carbon. Replacing hydrogen atoms by
chlorine atoms is an oxidation

When organic compound is oxidised, oxidising agent used is reduced. When an organic
compound is reduced, the reducing agent used must be oxidized.
1.2 Oxidation of Alkanes
Different products are formed by the use of different oxidising agents or different reaction
conditions.
(i) 𝐁𝐲 𝐊𝐌𝐎𝐎 or 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 : Alkanes are usually not affected by oxidising agents like 𝐊𝐌𝐧𝐎𝟒 or
𝟒

𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 . However, alkanes having tertiary hydrogen are oxidised by these oxidising agents to
an alcohol.
(CH3 )3 CH ⎯⎯⎯
KMnO
→ (CH3 )3 COH
4

(Isobutane) ( Tertiary butylalcohol )

𝐂𝐮/𝟓𝟐𝟑 𝐊/𝟏𝟎𝟎𝟎 𝐚𝐭𝐦

Ex. (a) 𝟐𝐂𝐇𝟒 + 𝐎𝟐 ⟶ 𝟐𝐂𝐇𝟑 𝐎𝐇 (methanol)
𝟗:𝟏
𝐌𝐨𝟐 𝐎𝟑
(b) 𝐂𝐇𝟒 + 𝐎𝟐 𝐇𝐂𝐇𝐎 + 𝐇𝟐 𝐎
𝚫
(𝐂𝐇𝟑 𝐂𝐎𝐎𝟐 )𝐌𝐧 𝐁𝐮𝐫𝐧
(c) 𝟐𝐂𝐇𝟑 − 𝐂𝐇𝟑 + 𝟑𝐎𝟐 𝟐𝐂𝐇𝟑 𝐂𝐎𝐎𝐇 + 𝟐𝐇𝟐 𝐎(𝐢𝐯) 𝐂𝐇𝟒 + 𝐎𝟐 ⟶ 𝐂 + 𝟐𝐇𝟐 𝐎
𝚫 𝐥𝐢𝐦𝐢𝐭𝐞𝐝 𝐜𝐚𝐫𝐛𝐨𝐧
𝐛𝐥𝐚𝐜𝐤

1.3 Oxidation of alkenes and alkynes

(i) Baeyer reagent [cold dilute 𝟏% alkaline 𝐊𝐌𝐧𝐎𝟒 solution] :
Alkene ⟶ Vicinal diol; Alkyne ⟶ Diketone; Aldehyde ⟶ Acid

APNI KAKSHA 2
(ORGANIC CHEMISTRY) REDUCTION OXIDATION

(ii) Oxidation with peroxyacids

An alkene is converted to an epoxide by a peroxyacid. [a carboxylic acid that has an extra
oxygen atom in 𝐚 − 𝐎 − 𝐎 − (peroxy) linkage]. Some simple peroxyacids (sometimes called
peracids) are shown below :

(a) (b)

(c) (d)
General Reaction

Stereochemistry : anti addition in diol formation.

Ex.

Note : The more highly substituted olifinic bond is more nucleophilic and therefore reacts faster with
the peroxyacid than the less susbstituted double bond.

(iii) Oxidation with acidic 𝐊𝐌𝐧𝐎𝟒 [𝐊𝐌𝐧𝐎𝟒 /𝐇 + ]:

When alkene & alkyne heated with 𝐊𝐌𝐧𝐎𝟒 in acidic or in alkaline medium; following changes
takes place.

APNI KAKSHA 3
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
𝐊𝐌𝐧𝐎𝟒 /𝐇 +
Reactant = 𝐂𝐇𝟐 group = 𝐂𝐇𝐑 group = 𝐂𝐑 𝟏 𝐑 𝟐 group ≡ 𝐂𝐇 group ≡ 𝐂𝐑 group
Product 𝐂𝐎𝟐 𝐑𝐂𝐎𝐎𝐇 𝐎 = 𝐂𝐑 𝟏 𝐑 𝟐 group 𝐂𝐎𝟐 𝐑𝐂𝐎𝐎𝐇

Ex.

(iv) Oxidation with ozone (ozonolysis):

Like permanganate ozone cleaves double bonds to give Ketones and aldehydes. However,
ozonolysis is milder, and both Ketones and aldehydes can be recovered without further
oxidation.
Reductive Ozonolysis:
𝐎𝟑 /𝐙𝐧, 𝐇𝟐 𝐎
Reactant = 𝐂𝐇𝟐 group = 𝐂𝐇𝐑 group = 𝐂𝐑 𝟏 𝐑 𝟐 group ≡ 𝐂𝐇 group ≡ 𝐂𝐑 group
Product 𝐇𝐂𝐇𝐎 𝐑𝐂𝐇𝐎 𝐑𝟏𝐑𝟐 𝐂 = 𝐎 −𝐂𝐎 − 𝐂𝐇𝐎 diketone
Reductive Ozonolysis:
𝐎𝟑 /𝐇𝟐 𝐎𝟐
Reactant = 𝐂𝐇𝟐 group = 𝐂𝐇𝐑 group = 𝐂𝐑 𝟏 𝐑 𝟐 group ≡ 𝐂𝐇 group ≡ 𝐂𝐑 group
Product 𝐂𝐎𝟐 𝐑𝐂𝐎𝐎𝐇 𝐑𝟏𝐑𝟐 𝐂 = 𝐎 𝐂𝐎𝟐 𝐑𝐂𝐎𝐎𝐇

Very
Type of Milder
Strong
Oxidising oxidising Mild oxidising agent Strong oxidising agent
oxidising
agent → agent
agent
Oxidising
𝐂𝐫𝐎𝟑 in
agent→ 𝐂𝐫𝐎𝟑 in
water 𝐊𝐌𝐧𝐎𝟒 / 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 / 𝐊𝐌𝐧𝐎𝟒 /
Type of 𝐂𝐮, 𝚫(𝟑𝟎𝟎∘ 𝐂) PCC PDC Inert
or 𝐇+ 𝐇+ 𝐇 + /Heat
Alcohol medium
𝐇𝟐 𝐂𝐫𝐎𝟒
↓

APNI KAKSHA 4
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
𝟏∘ alcohol or
Carboxylic
Primary Aldehyde Aldehyde Carboxylic acid
acid
alcohol
𝟐∘ alcohol or Mixture of
Primary Ketone Ketone Ketone Carboxylic
alcohol acid
𝟐∘ alcohol or Mixture of
Dehydrate to
Primary Not oxidised Not oxidised Carboxylic
Alkene
alcohol acid

1.4 Oxidation Reaction of Alcohols :

(i) Oxidation of alcohols using 𝐂𝐫(𝐕𝐈) reagents:
For oxidation of alcohols to corresponding carbonyl compounds, generally 𝐂𝐫(𝐕𝐈) reagents such
as 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 , Jones reagent, PCC etc. are employed. For the synthesis of aldehydes, the Collins
Reaction or use of more modern although more expensive chromium (VI) reagents such as PCC
and PDC can be an appropriate choice. Oxidation of alcohols to carbonyl compound occurs via
𝐂𝐫(𝐕𝐈) acid monoester. Oxidation of fused aromatic system is generally carried out using 𝐂𝐫𝐎𝟑
reagent
(a) PCC (Pyridinium Chloro Chromate)
It is other efficient reagent used widely for oxidation of primary and secondary alcohols. Reagent
can be used in close to stoichiometric amounts with substrate. PCC is slightly acidic but can be
buffered with 𝐍𝐚𝐎𝐀𝐜.
As no water is present in the reaction mixture, no aldehyde hydrate is formed which is oxidized
to carboxylic acid in presence of 𝐂𝐫(𝐕𝐈)

(b) PDC (Pyridinium Dichromate): Since PDC is less acidic than PCC it is often used to oxidize
alcohols that may be sensitive to acids. In methylene chloride solution, PDC oxidizes primary and
secondary alcohols in roughly the same fashion as PCC, but much more slowly. Allylic alcohols
are oxidized efficiently to conjugated enals and enones respectively.

APNI KAKSHA 5
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
(c) Collins Reagent: It is the mixture of chromium trioxide with pyridine in dichloromethane. It is
used to selectively oxidize primary alcohols to aldehyde, and will tolerate many other functional
groups in the molecule.
It can be used as an alternative to Jones reagent and PCC in oxidation of secondary alcohols.
Moreover, Collins reagent is especially useful for oxidations of acid sensitive compounds. Collins
reagent can be prepared and isolated or generated in situ. This complex is both difficult and
dangerous to prepare, as it is very hygroscopic and can in flame during its preparation.

(d) Jones Reagent : It is chromium oxide, sulfuric acid and acetone. A mixture of potassium or
sodium dichromate and dilute sulfuric acid can also be used.
It is a powerful oxidizing reagent and exhibits only poor chemoselectivity.
It is used for the oxidation of primary and secondary alcohols to carboxylic acids and ketones,
respectively, that do not contain acid sensitive group.
Chromic acid and alcohol then through chromate ester gives carbonyl compound in presence of
base (water in this case).
Aldehydes can form hydrates in presence of water and further oxidized to carboxylic acid in
presence of 𝐂𝐫(𝐕𝐈) reagents. Tertiary alcohols cannot be oxidized by this reagent.
(ii) Oxidation using Mn reagents
(a) 𝐌𝐧𝐎𝟐 : It is used widely as oxidant in organic synthesis. It oxidizes allylic alcohols,
acetylenicalcohols and benzylic alcohols to corresponding aldehydes or ketones. The
configuration of double bond is preserved in the reaction.
(b) 𝐊𝐌𝐧𝐎𝟒 : Manganese can function as oxidant when it is in +7 oxidation state. 𝐊𝐌𝐧𝐎𝟒 is one such
oxidant. It is a very strong oxidizing agent.
Alkyl side chainson aromatic rings are oxidized to carboxylic acid group. This method is more
generally applied to methyl group, however, longer side chains can also be cleaved. Tertiary alkyl
groups are not oxidized and are usually accompanied by ring cleavage. 𝐊𝐌𝐧𝐎𝟒 is also used to
oxidize primary alcohol andaldehyde to corresponding carboxylic acid.
Ex. Write the product of following reaction when 𝐗 istreated with
(i) Jones reagent (ii) 𝐏𝐂𝐂 (iii) Oppenauer oxidation (iv) 𝐌𝐧𝐎𝟐 (v) 𝐊𝐌𝐧𝐎𝟒
𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇
𝐎𝐇
(X)

APNI KAKSHA 6
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
(c) Oppenaur's oxidation
(i) This reaction involves the oxidation of a secondary alcohol with a ketone and base to the
corresponding ketone.
(ii) Commonly used bases are aluminium tert-butoxide.

(d) Kornblum oxidation [(i) DMSO (ii) 𝐍𝐚𝐇𝐂𝐎𝟑 ]

𝐃𝐌𝐒𝐎
(i) 𝐑𝐂𝐇𝟐 𝐗 ⟶ 𝐑𝐂𝐇𝐎;
𝐍𝐚𝐇𝐂𝐎𝟑
𝐃𝐌𝐒𝐎
(ii) 𝐑 𝟐 𝐂𝐇 − 𝐗 ⟶ 𝐑 𝟐 𝐂𝐎;
𝐍𝐚𝐇𝐂𝐎𝟑
DMSO
(iii) 𝐑 𝟑 𝐂 − 𝐗 ⟶ No oxidation
𝐍𝐚𝐇𝐂𝐎𝟑

1.5 Oxidation reaction of Carbonyl Compound

(i) Popoff's rule (Acidic 𝐊𝐌𝐧𝐎𝟒 & 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 as oxidising agent) :
(a) Aldehydes are oxidised to carboxylic acid having same number of 𝐂 atoms as aldehyde.
𝐇𝐂𝐇𝐎 + [𝐎] ⟶ 𝐇𝐂𝐎𝐎𝐇; 𝐑𝐂𝐇𝐎 + [𝐎] ⟶ 𝐑𝐂𝐎𝐎𝐇
(b) Ketones are oxidised with difficulty.
They are oxidised only on heating with a strong oxidising agent.

(c) In case of mixed or unsymmetrical ketones the > 𝐂 = 𝐎 group remains with the smaller
alkyl group.
[𝐎]
𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝟐 𝐂𝐇𝟑 ⟶ 𝟐𝐂𝐇𝟑 𝐂𝐎𝐎𝐇; 𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐇𝟑
[𝐎]
⟶ 𝐂𝐇𝟑 𝐂𝐎𝐎𝐇𝟑 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇
Mechanism (with 𝐂𝐫 +𝟔 oxidising agents) :

(a)

(b)

APNI KAKSHA 7
(ORGANIC CHEMISTRY) REDUCTION OXIDATION

(C)

Remarks :
Primary alcohol forms a chromate ester with chromic acid.
The chromate ester decomposes in 𝟐nd slow step with the elimination of 𝜶-hydrogen. So the first
oxidation product, an aldehyde is obtained.
In aqueous medium, aldehyde forms a gemdiol (hydrated aldehyde). It is further oxidised to an
acid by similar mechanism.
(ii) TOLLEN'S REAGENT :
𝐑𝐂𝐇𝐎 (aldehydes) can be easily oxidised to 𝐑𝐂𝐎𝐎𝐇 (except 𝐇𝐂𝐇𝐎 that can be oxidised to 𝐂𝐎𝟐
) by weak oxidising agents like ammonical 𝐀𝐠𝐍𝐎𝟑 (Tollen's reagent) hence they are better
reducing agents.
Aldehydes reduce Tollen's reagent to Ag and appears in the form of silver mirror is called silver-
mirror test. It is given by all aldehydes and reducing sugars.
𝚫
𝐑𝐂𝐇𝐎 + 𝟐[𝐀𝐠(𝐍𝐇𝟑 )+ − −
𝟐 ] + 𝟑𝐎𝐇 ⟶ 𝐑𝐂𝐎𝐎 + 𝟐𝐀𝐠 ↓ +𝟒𝐍𝐇𝟑 + 𝟐𝐇𝟐 𝐎

(iii) FEHLING SOLUTION :

Aldehydes (except benzaldehyde) reduce Fehling's solution (𝐂𝐮𝟐+ reduced to 𝐂𝐮+ )which is
an alkaline solution of cupric (𝐂𝐮𝟐+ ) ion complexed with tartrate ion.
𝚫
𝐑𝐂𝐇𝐎 + 𝟐𝐂𝐮𝟐+ + 𝟓𝐎𝐇 − ⟶ 𝐑𝐂𝐎𝐎− + 𝐂𝐮𝟐 𝐎 ↓+ 𝟑𝐇𝟐 𝐎
redppt.

(iv) BENEDICT'S SOLUTION :

Aldehydes also reduce Benedict's solution (𝐂𝐮𝟐+ complexed with citrate ion) to 𝐂𝐮+ Sodium
citrate +𝐍𝐚𝐎𝐇 + 𝐍𝐚𝐇𝐂𝐎𝟑 + 𝐂𝐮𝐒𝐎𝟒

(v) 𝐇𝐠𝐂𝐥𝟐 and 𝐇𝐠 𝟐 𝐂𝐥𝟐

(i) 𝐑𝐂𝐇𝐎 + 𝐇𝐠𝐂𝐥𝟐 + 𝐇𝟐 𝐎 ⟶ 𝐑𝐂𝐎𝐎𝐇 + 𝟐𝐇𝐂𝐥 + 𝐇𝐠 𝟐 𝐂𝐥𝟐
𝚫

(ii) 𝐑𝐂𝐇𝐎 + 𝐇𝐠 𝟐 𝐂𝐥𝟐 + 𝐇𝟐 𝐎 → 𝐑𝐂𝐎𝐎𝐇 + 𝟐𝐇𝐂𝐥 + 𝟐𝐇𝐠 ↓ grey ppt.

(vi) SCHIFF'S REAGENT:
Schiff's Reagent is aq. solution of following base decolourised by passing 𝐒𝐎𝟐 . Aldehyde restore
pink colour of Schiff's reagent.

APNI KAKSHA 8
(ORGANIC CHEMISTRY) REDUCTION OXIDATION

Note: Ketons are not easy to oxidize so they do not give these 5 tests. These five tests can be used
to distinguish aldehyde and ketones. Both gives 2, 4 DNP test.
(vii) Oxidation by using 𝐒𝐞𝐎𝟐 : −𝐒𝐞𝐎𝟐 is a selective oxidizing agent with converts −𝐂𝐇𝟐 −
group agjacent
to carbonyl group into carbonyl group. The reagent, in general, oxidises active methylene and
methyl
groups to ketonic and aldehydic groups respectively.

-Double bonds, triple bonds and aromatic rings may also activate the methylene group. The
methylene or methyl group 𝜶 to the most highly substitued end of the double bond is
hydroxylated according to the order of preference of oxidation 𝐂𝐇𝟐 > 𝐂𝐇𝟑 > 𝐂𝐇 groups.

-Rate of reactivity order : 𝟐∘ 𝐂 − 𝐇 > 𝟏∘ 𝐂 − 𝐇 > 𝟑∘ 𝐂 − 𝐇

(viii) BAEYER-VILLIGER OXIDATION: It is the oxidative cleavage of a carbon-carbon bond

adjace to a carbonyl which converts ketones to esters and cyclic ketones to lactones.
It can be carried out with peracids such as m-CPBA, or with hydrogen peroxide and a lewis acid.

APNI KAKSHA 9
(ORGANIC CHEMISTRY) REDUCTION OXIDATION

KETONES ARE DIFFICULT TO OXIDIZE : Ketones can be oxidized from their enolic form at high
temperature with very strong oxidizing agent. Oxidation of ketones is sometimes governed by
Popoff's rule. According to this rule carbonyl group remains with the smaller alkyl group. More
electron rich alkene will be easy to oxidized.

(ix) DIOLS OXIDATION BY 𝐇𝐈𝐎𝟒 : (Oxidation by lead acetate is similar to 𝐇𝐈𝐎𝟒 oxidation)

Mechanism:
Remarks :
• 𝐇𝐈𝐎𝟒 (periodic acid) oxidises vicinal diols (1, 2-diols).
• It brings about oxidative cleavage of vicinal diol.
• It can also oxidise 𝜶-hydroxy carbonyl compound, 𝜶-dicarbonyl compound and 𝜶 hydroxy Imine.
• 𝐇𝐈𝐎𝟒 forms a cyclic periodate ester as an intermediate.
General reaction

APNI KAKSHA 10
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
EXERCISE # I
1. Tollen's reagent is

(A) 𝐂𝐮𝟐 𝐎 (B) [𝐂𝐮(𝐎𝐇)𝟒 ]𝟐− (C) 𝐀𝐠𝐎𝐇 (D) [𝐀𝐠(𝐍𝐇𝟑 )𝟐 ]+

2. Major product of following reaction is:

(A) (B)

(C) (D)

3. Baeyer's reagent decolourises when reacts with:

(A) Alkane (B) Alkene only

(C) Alkene and alkyne both (D) Alkyne only

4. The end products of the reaction are:

(A) (B)

(C) (D) Propane

5. X and Y in following reaction is:

KMnO4 / 
1 − Butyne ⎯⎯⎯⎯ →X + Y

(A) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇 + 𝐎𝟐 (B) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇

(C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇 + 𝐂𝐎𝟐 (D) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐂𝐇𝟑 + 𝐇𝐂𝐎𝐎𝐇

APNI KAKSHA 11
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
6. Major product of following reaction is/are:

(A) (B)

(C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐎𝐇 (D)

7. Bayer's reagent is:
(A) alkaline permanganate solution (B) acidified permanganate solution
(C) neutral permanganate solution (D) aqueous bromine solution
8. An alkyne 𝐂𝟕 𝐇𝟏𝟐 when reacted with alkaline 𝐊𝐌𝐧𝐎𝟒 followed by acidification by 𝐇𝐂𝐥, yielded a
mixture of &𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇. The alkyne is –

(A) 3-hexyne (B) 2-methyl-2-hexyne

(C) 2-methyl-3-hexyne (D) 3-methyl-2-hexyne
9. 𝐑 𝟏 and 𝐑 𝟐 in following reaction respectively is :

(A) Cold alkaline 𝐊𝐌𝐧𝐎𝟒 , 𝐎𝐬𝐎𝟒 /𝐇𝟐 𝐎𝟐 (B) Cold alkaline 𝐊𝐌𝐧𝐎𝟒 , 𝐇𝐂𝐎𝟑 𝐇&𝐇𝟑 𝐎+
(C) Cold alkaline 𝐊𝐌𝐧𝐎𝟒 , 𝐂𝟔 𝐇𝟓 𝐂𝐎𝟑 𝐇 (D) 𝐂𝟔 𝐇𝟓 𝐂𝐎𝟑 𝐇, 𝐇𝐂𝐎𝟑 𝐇
10. Which of the following is/are hydrocarbon?

(A) 𝐏 (B) 𝐐 (C) 𝐑 (D) 𝐒

11. Glucose as well as fructose are oxidized by periodic acid. The number of moles of 𝐇𝐂𝐎𝐎𝐇
formed from each mole of glucose and fructose are
(A) 5 and 5 (B) 5 and 4 (C) 5 and 3 (D) 4 and 312
APNI KAKSHA 12
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
12. Major products of the given reaction will be:

(A) (B) (C) (D) Both (B) and (C)

13. Fehlings solution is

(A) 𝐀𝐠𝐍𝐎𝟑 solution +𝐍𝐚𝐎𝐇 solution +𝐍𝐇𝟒 𝐎𝐇
(B) Alkaline solution of Cupric ion complexed with citrate ion
(C) Copper sulphate + sodium potassium tartarate +𝐍𝐚𝐎𝐇
(D) Copper sulphate solution
14. Secondary alcohols on heating with copper at 𝟑𝟎𝟎∘ 𝐂 give
(A) Alkenes (B) Aldehydes (C) Ketones (D) tert-alcohols
15. The reagent which can react easily with both acetaldehyde and acetone is:
(A) Tollens reagent (B) Schiffs reagent (C) 𝐇𝟐 /𝐍𝐢 (D) Fehling's solution
16. Which of the following compounds is resistant to periodic acid oxidation?

(A) (B) (C) (D)

17. Identify (P) and (Q) respectively in the given reaction :

(A) (B)

(C) (D)

APNI KAKSHA 13
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
18. Which of the following sets of compounds cannot turn clear orange solution of 𝐂𝐫𝐎𝟑 / aq. 𝐇𝟐 𝐒𝐎𝟒
to greenish opaque solution

(A) I, IV (B) II, III (C) I, II (D) III, IV

19. Major product of following reaction is/are:

(A) 𝐑 − 𝐂𝐇𝐎 (B) 𝐑 − 𝐂𝐇𝟐 𝐎𝐇 (C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐎𝐇 (D) 𝐑 − 𝐂𝐎𝐎𝐇

20. Major product is :

(A) (B)

(C) (D)

21. The product which is not formed in the following reaction is:

(A) HCOOH (B) (C) (D)

APNI KAKSHA 14
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
22. The products of acid hydrolysis of 𝐏 and 𝐐 can be distinguished by:

(A) Lucas reagent (B) 2, 4-DNP (C) Fehling's solution (D) 𝐍𝐚𝐇𝐒𝐎𝟑
23. On catalytic reduction with 𝐇𝟐 /𝐏𝐭 how many alkenes will give 𝐧-butane ?
(A) 1 (B) 2 (C) 3 (D) 4
24. Major products of following reaction will be :

(A) Racemic mixture (B) Diastereomers

(C) Meso (D) Constitutional isomers
25. Alkene 𝐗 in following reaction is :

(A)

(B)

(C)

(D)
26. Which reagent will be used for the given conversion?

(A) 𝐍𝐚/ Liq. 𝐍𝐇𝟑 (B) 𝐇𝟐 , 𝐏𝐝 − 𝐂𝐚𝐂𝐎𝟑 (C) 𝐋𝐢, 𝐏𝐡 − 𝐍𝐇𝟐 (D) 𝐇𝟐 , 𝐏𝐭

APNI KAKSHA 15
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
27. In following reaction A and B respectively are:

(A)

(B)

(C)

(D)

28. Which of the following will decolorise alkaline 𝐊𝐌𝐧𝐎𝟒 solution?

(A) 𝐂𝟑 𝐇𝟖 (B) 𝐂𝐇𝟒 (C) 𝐂𝐂𝐥𝟒 (D) 𝐂𝟐 𝐇𝟒
29. Product 𝐁 and 𝐂 in given reaction are respectively:
OsO4 HIO4
2 − methylbut − 2 − ene ⎯⎯ ⎯
H2O2
→ A ⎯⎯→ B+C

(A)

(B)

(C)

(D)

30. If the following compound is treated with 𝐏𝐝 in excess of 𝐇𝟐 gas, how many stereoisomers of
the product will be obtained?

(A) 1 (B) 2 (C) 3 (D) 4

APNI KAKSHA 16
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
31. Major product of following reaction is :

(A) (B)

(C) (D) All of these

32. Which of the following can not be obtained when alkenes are oxidised with 𝐊𝐌𝐧𝐎𝟒 and then
followed by acid hydrolysis?
(A) alkanoic acids (B) alkanols (C) alkanones (D) carbon dioxide
33. Which alkyne gives 3 -ethylhexane on catalytic hydrogenation?

(A) (B)

(C) (D)
34. The final major product (𝐁) in following reaction is :

(A) (B) (C) (D)

35. In following reaction if (𝐁) and (𝐂) both give + ve iodoform test then compound (𝐀) can be :

(A) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇 − 𝐎 − 𝐂𝐇𝟐 − 𝐂𝐇𝟑 (B)

(C) (D) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐎 − 𝐂𝐇𝟐 − 𝐂𝐇𝟑

APNI KAKSHA 17
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
36. Which of the following can be selectively oxidised by 𝐌𝐧𝐎𝟐 /𝚫 :
(A) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇𝐎𝐇 − 𝐂𝐇𝟑 (B) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇
(C) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐎𝐇 (D) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇
37. Which will give silver mirror test with Tollens reagent :
(A) 𝐂𝟔 𝐇𝟓 𝐂𝐇𝐎 (B) 𝐂𝐇𝟑 − 𝐂𝐇𝐎 (C) 𝐇𝐂𝐎𝐎𝐇 (D) 𝐂𝟔 𝐇𝟓 𝐂𝐇(𝐎𝐇)𝐂𝐎𝐂𝟔 𝐇𝟓
38. Fehling solution gives red precipitate with:
(A) Aromatic aldehyde (B) Aliphatic aldehyde

(C) Ketones (D)

39. Choose the major product of the follolwing reaction.

(A) (B)

(C) (D)

40. Silver mirror test with Tollens reagent is given by:

(A) 𝐂𝟔 𝐇𝟓 𝐂𝐇𝐎 (B) 𝐏𝐡 − 𝐍𝐇 − 𝐎𝐇
(C) (D) 𝐂𝐇𝟑 𝐂𝐇𝐎

41. Major product of following reaction is:

(A) 𝐏𝐡 − 𝐂𝐇𝟐 𝐎𝐇 (B) 𝐍𝐇𝐌𝐞𝟐 (C) 𝐏𝐡 − 𝐂𝐇𝟐 − 𝐍𝐌𝐞𝟐 (D) 𝐏𝐡 − 𝐂𝐇𝐎

APNI KAKSHA 18
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
EXERCISE # II
1. In which of the following reactions reactant and product both can show stereoisomerism:

(A) (B)

(C) (D)

2. Which of the following is an example of oxidation reaction:

𝐏𝐂𝐥𝟑 𝐍𝐢/𝐇𝟐
(A) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐎𝐇 ⟶ (B) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇𝟐 ⟶
𝐁𝐫𝟐 𝐃𝐌𝐒𝐎/𝐍𝐚𝐇𝐂𝐎𝟑
(C) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇𝟐 ⟶ (D) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐥 ⟶
𝐂𝐂𝐥𝟒

3. In following reaction sequence compound B is:

CHO
|
(A) CHO (B) 𝐂𝐇𝟑 − 𝐂𝐇𝐎 (C) 𝐂𝐇𝟑 − 𝐂𝐎𝐎𝐇 (D) 𝐇 − 𝐂𝐎𝐎𝐇

4. Major product of which reaction can show Stereoisomerism?

𝐏𝐂𝐂
(A) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐎𝐇 ⟶

(B)

(C) C6H5 − CH = CH − CH2 − CH − CH2 − OH ⎯⎯⎯⎯⎯

TsCl
DMSO,NaHCO3
→
|
CH3

(D)

APNI KAKSHA 19
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
5. Which of the following compound will give positive Tollens test

(A) Tartaric acid (B)

(C) CH3CH2CH2CH2CH − OCH3 (D)

|
OH
6. Which of the following reactions is/are correctly match with their major products?

(A) (B)

(C) (D)

7. Which one of the following alcohols are oxidised by 𝐌𝐧𝐎𝟐 ?

(A) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇 (B)

(C) (D) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇

8. Which will give the Tollen test.

(A) (B) (C) (D)

9. Major product and reactant of which reactions gives positive tollens test:

(A) (B)

HIO4
OHCCH2OH ⎯⎯→
(C) (D) 

APNI KAKSHA 20
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
10. In following reaction 𝐏 and 𝐐 are respectively.

(A) Acetone and Hexane-1,2,5,6-tetraol.

(B) Acetaldehyde and Acetone.
(C) Acetaldehyde and Hexane-1,2,5,6-tetraol.
(D) Acetone and Formaldehyde.

11. Choose the incorrect option(s) for following sequence.

(A) 𝐏 is a racemic compound (B) Q is terminal alkyne

(C) 𝐗&𝐑 are positional isomer (D) Formation of 𝐑 is redox reaction
12. Which of the following compounds will consume even number of periodic acid?
(A) HO − CH2 − CH2 − CH − CH2 − OH (B) CH2 — CH − CH − CH2
| | | | |
OH OH OH OH OH
(C) H2C — CH − CH − CH3 (D) Me − C − CH − Me
| | | || |
OH OH OH O NH2

13. Which of the following is correctly matched?

(A) (B)

(C) (D)

APNI KAKSHA 21
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
14.
Column-I (Conversion) Column-II
(Required
Reagent)
(A) (P) 𝐇𝟐 , 𝐏𝐝 − 𝐁𝐚𝐒𝐎𝟒

(B) (Q) Li, Liq. 𝐍𝐇𝟑

(C) 𝐇𝟑 𝐂 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝟑 ⟶ 𝐇𝟑 𝐂 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − (R) 𝐍𝟐 𝐇𝟒 /𝐇𝟐 𝐎𝟐

𝐂𝐇𝟑
(D) (S) 𝐁𝟐 𝐇𝟔 , 𝐂𝐇𝟑 𝐂𝐎𝐎𝐇

15. Total number of alcohols obtained in following reaction is:

16. Total numbers of reagent that can be used for given conversion.

⊖
(a) 𝐙𝐧 − 𝐇𝐠/𝐇𝐂𝐥 (b) 𝐋𝐢𝐀𝐥𝐇𝟒 (c) 𝐋𝐢𝐁𝐇𝟒 (d) ( i )𝐍𝟐 𝐇𝟒 (ii) 𝐎𝐇, 𝚫
(e) 𝐋𝐢𝐀𝐥(𝐎𝐄𝐭)𝟑 𝐇 (f) 𝐑𝐞𝐝 𝐏/𝐇𝐈 (g) (i) (𝐂𝐇𝟐 𝐒𝐇)𝟐 (ii) 𝐇𝟐 , Raney 𝐍𝐢

COMPREHENSION TYPE Paragraph for Q. 17 to 21

17. The compound (𝐂) is:

(A) (B) (C) 𝐄𝐭−≡ −𝐄𝐭 (D) Both (A) and (B)
APNI KAKSHA 22
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
18. The compound (𝐅) is:

(A) (B) (C) 𝐄𝐭−≡ −𝐄𝐭 (D) Both (A) and (B)
19. The compound (𝐃) is:

(A) (B) (C) (D) Both (B) and (C)

20. The compound (𝐆) is:

(A) (B) (C) (D) None of these

21. The compound (𝐄) is:

(A) (B)
(C) One mole of (𝐀) and one mole of (𝐁) (D) No reaction.
22. Reaction of 2-butanol with 𝐂𝐮, 𝚫 involve
(A) dehydrogenation (B) elimination
(C) dehydration (D) oxidation
23. Which of the following will give syn addition?

(A) (B)

(C) (D)

SUBJECTIVE TYPE
24. Complete the following reactions:

(a) (b) (c)

APNI KAKSHA 23
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
25. Complete the following reactions:

26. How many alkene on catalytic reduction give normal butane as product.
𝐇𝟐 /𝐏𝐭 𝐇𝟐 /𝐏𝐭 𝐇𝟐 /𝐏𝐭
(i) (A) ⟶ n-butane (ii) (B) ⟶ Iso-pentane (iii) (C) ⟶ Neo-pentane

𝐇𝟐 /𝐏𝐭 𝐇𝟐
(iv) (D) ⟶ Cyclopentane (v) (E) ⟶
𝐏𝐭

27. Give the expected major product for each reaction, including stereochemistry where
applicable.

28. Give product in the following reactions

APNI KAKSHA 24
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
EXERCISE # III (MAIN & ADVANCE)
1. Hydrogenation of benzoyl chloride in the presence of 𝐏𝐝 and 𝐁𝐚𝐒𝐎𝟒 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
2. Draw the stereochemical structure of the product in the following reactions. [IIT 1994]
H2
R − C  C − R ⎯⎯⎯⎯⎯
Lindlarcatalyst
→

3. Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
[IIT 1995]
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
4. In the reaction, 𝐏 is [IIT 1995]

(A) 𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝐎 (B) 𝐂𝐇𝟑 𝐂𝐎𝐎𝐂𝐇𝟑 (C) 𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝟐 𝐎𝐇 (D) None
5. Which one of the following alkenes will react fastest with 𝐇𝟐 under catalytic hydrogenation
condition [IIT 2000]

(A) (B) (C) (D)

6. The appropriate reagent for the following transformation: [IIT-2000]

(A) 𝐙𝐧(𝐇𝐠), 𝐇𝐂𝐥 (B) 𝐍𝐇𝟐 𝐍𝐇𝟐 , 𝐎𝐇 − (C) 𝐇𝟐 /𝐍𝐢 (D) 𝐍𝐚𝐁𝐇𝟒

7.

Hydrogenation of the above compound in the presence of poisoned paladium catalyst gives-
[IIT-2001]
(A) An optically active compound (B) An optically inactive compound
(C) Aracemic mixture (D) Adiastereomeric mixture
8. When 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐎𝐎𝐇 is reduced with 𝐋𝐢𝐀𝐥𝐇𝟒 , the compound obtained will be –
[AIEEE-2003]
(A) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 𝐎𝐇 (B) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝐎
(C) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐎𝐎𝐇 (D) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐇𝟐 𝐎𝐇

APNI KAKSHA 25
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
9. 2-hexyne can be converted into trans-2-hexene by the action of: [IIT-2004]
(A) 𝐇𝟐 − 𝐏𝐝 − 𝐁𝐚𝐒𝐎𝟒 (B) 𝐋𝐢 in liq. 𝐍𝐇𝟑
(C) 𝐇𝟐 − 𝐏𝐭𝐎𝟐 (D) 𝐍𝐚𝐁𝐇𝟒
10. The best reagent to convert pent-3-en-2-ol into pent-3-en-2-one is [AIEEE 2005]
(A) Acidic dichromate (B) Acidic permanganate
(C) Pyridinium chloro-chromate (D) Chromic anhydride in glacial acetic acid
Paragraph for Question No. 11 to 13
In the following reaction sequence, products 𝐈, 𝐉 and 𝐋 are formed. 𝐊 represents a reagent.

11. The structure of the product 𝐈 is [JEE-2008]

(A) (B)

(C) (D)
12. The structures of compounds 𝐉 and 𝐊, respectively, are [JEE-2008]

(A) (B)

(C) (D)
13. The structure of product 𝐋 is [JEE-2008]

(A) (B)

(C) (D)
14. Which of the following will change the colour of acidic dichromate solution.
[JEE Mains-2013]

(A) (B)

(C) (D)

APNI KAKSHA 26
(ORGANIC CHEMISTRY) REDUCTION OXIDATION

15. [JEE Mains-2013]

(A) (B)

(C) (D)

16. Major product of reaction is? [JEE Mains-2013]

(A) (B) (C) (D)

17. The most suitable reagent for the conversion of 𝐑 − 𝐂𝐇𝟐 − 𝐎𝐇 → 𝐑 − 𝐂𝐇𝐎 is
[JEE Mains 2014]
(A) 𝐂𝐫𝐎𝟑 (B) PCC (Pyridinium chlorochromate)
(C) 𝐊𝐌𝐍𝐎𝟒 (D) 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕
18. Consider all possible isomeric ketones including stereoisomers of 𝐌𝐖 = 𝟏𝟎𝟎, All these isomers
are independently reacted with 𝐍𝐚𝐁𝐇𝟒 (NOTE : stereoisomers are also reacted separately) The
total number of ketones that give a racemic product(s) is/are. [JEE-2014]
19. In the reaction [JEE-2014]
𝐋𝐢𝐀𝐥𝐇𝟒 𝐏𝐂𝐥𝟓 𝐀𝐥𝐂𝐊𝐎𝐇
𝐂𝐇𝟑 𝐂𝐎𝐎𝐇 ⟶ 𝐀 ⟶ 𝐁 ⟶ 𝐂. Final Product 𝐂 is.
(A) 𝐇𝟐 / Lindlar Cat. (B) Cat. hydrogenation
(C) 𝐋𝐢𝐀𝐥𝐇𝟒 (D) 𝐋𝐢/𝐍𝐇𝟑
20. The reagent needed for converting is: [JEE-2014]

(A) 𝐇𝟐 / Lindlar Cat. (B) Cat. hydrogenation

(C) 𝐋𝐢𝐀𝐥𝐇𝟒 (D) 𝐋𝐢/𝐍𝐇𝟑

APNI KAKSHA 27
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
21. Reagent(s) which can be used to bring about the following transformation is(are): [JEE-2016]

(A) 𝐋𝐢𝐀𝐥𝐇𝟒 in (𝐂𝟐 𝐇𝟓 )𝟐 𝐎 (B) 𝐁𝐇𝟑 in 𝐓𝐇𝐅

(C) 𝐍𝐚𝐁𝐇𝟒 in 𝐂𝟐 𝐇𝟓 𝐎𝐇 (D) Raney 𝐍𝐢/𝐇𝟐 in THF
22. The major product obtained in the following reaction is: [JEE MAINS-2017]

(A) (B)

(C) (D)

(𝟏)𝐀𝐥𝐇(𝐢−𝐁𝐮𝟐 )
23. The major product of following reaction is : 𝐑 − 𝐂 ≡ 𝐍 ⟶ [JEE MAIN-2019]
(𝟐)𝐇𝟐 𝐎

(A) 𝐑𝐂𝐇𝐎 (B) 𝐑𝐂𝐎𝐎𝐇 (C) 𝐑𝐂𝐇𝟐 𝐍𝐇𝟐 (D) 𝐑𝐂𝐎𝐍𝐇𝟐

24. The major product ' 𝐗 ' formed in the following reaction is: [JEE MAIN-2019]

(A) (B)

(C) (D)

APNI KAKSHA 28
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
25. The product of the following reaction is: [JEE MAIN-2019]

(A) (B)

(C) (D)

26. The major product of the following reaction is: [JEE MAIN-2019]

(A) (B)

(C) (D)

27. The major product obtained in the following reaction is: [JEE MAIN-2019]

(A) (B)

(C) (D)

APNI KAKSHA 29
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
28. Which of the following compounds reacts with ethylmagnesium bromide and also
decolourizes bromine water solution [JEE MAIN-2019]

(A) (B)

(C) (D)

29. The major product of the following reaction is: [JEE MAIN-2019]

(A) (B) (C) (D)

30. The major product of the following reaction is: [JEE MAIN-2019]

(A) (B) (C) (D)

31. The major product(s) obtained in the following reaction is/are: [JEE MAIN-2019]

(A) (B)

(C) (D)

APNI KAKSHA 30
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
32. The major product of the following reaction is: [JEE MAIN-2019]

(A) (B)

(C) (D)

33. The major product of the following reaction is: [JEE MAIN-2019]
𝐋𝐢𝐀𝐥𝐇𝟒
𝐂𝐇𝟑 𝐂𝐇 = 𝐂𝐇𝐂𝐎𝟐 𝐂𝐇𝟑 ⟶
(A) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐇𝐎 (B) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐎𝟐 𝐂𝐇𝟑
(C) 𝐂𝐇𝟑 𝐂𝐇 = 𝐂𝐇𝐂𝐇𝟐 𝐎𝐇 (D) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐎𝐇
34. Which of the following is NOT a correct method of the preparation of benzylamine from
cyanobenzene? [JEE MAIN-2019]
(A) 𝐇𝟐 /𝐍𝐢 (B) (i) 𝐇𝐂𝐥/𝐇𝟐 𝐎 (ii) 𝐍𝐚𝐁𝐇𝟒
(C) (i) 𝐋𝐢𝐀𝐥𝐇𝟒 (ii) 𝐇𝟑 𝐎 +
(D) (i) 𝐒𝐧𝐂𝐥𝟐 + 𝐇𝐂𝐥 (gas) (ii)𝐍𝐚𝐁𝐇𝟒
(1)NaBH (2)PBr (3)Mg/Ether (4)CO (5)H
35. Hex-3-ynal ⎯⎯⎯⎯
4
→⎯⎯⎯
3
→⎯⎯⎯⎯→⎯⎯⎯
2
→⎯⎯⎯
→ (𝐗), formed product 𝐗 will be:
[JEE MAIN 2020]

(A) (B)

(C) (D)

36. Consider the following reactions [JEE MAIN 2020]

'A' ⎯⎯⎯⎯
Ozonolysis
→ 'B'+ 'C'
(C6H14 )

APNI KAKSHA 31
(ORGANIC CHEMISTRY) REDUCTION OXIDATION

(A) (B)

(C) (D)
`
37. Reagent used for the given conversion is: [JEE-MAIN 2020]

(A) 𝐇𝟐 , 𝐏𝐝 (B) 𝐁𝟐 𝐇𝟔 (C) 𝐍𝐚𝐁𝐇𝟒 (D) 𝐋𝐢𝐀𝐥𝐇𝟒

38. Three isomers 𝐀, 𝐁 and 𝐂( 𝐦𝐨𝐥. formula 𝐂𝟖 𝐇𝟏𝟏 𝐍) give the following results
[JEE-MAIN 2020]
Diazotization
𝐀 and 𝐂 ⟶
(𝐢𝐢)𝐎𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
(𝐢)𝐇𝐲𝐝𝐫𝐨𝐥𝐲𝐬𝐢𝐬 𝐑(𝐏𝐫𝐨𝐝𝐮𝐜𝐭𝐨𝐟𝐀)
(𝐊𝐌𝐧𝐎𝟒 +𝐇+ )
𝐏 + 𝐐→ +
𝐒(𝐏𝐫𝐨𝐝𝐮𝐜𝐭𝐨𝐟𝐂)
𝐑 has lower boiling point than 𝐒
𝐂𝟔 𝐇𝟓 𝐒𝐎𝟐 𝐂𝐥
𝐁 ⟶ alkali-insoluble product
𝐀, 𝐁 and 𝐂, respectively are

39. The most suitable reagent for the given conversion is: (JEE MAIN 2020)

(A) 𝐇𝟐 , 𝐏𝐝 (B) 𝐁𝟐 𝐇𝟔 (C) 𝐍𝐚𝐁𝐇𝟒 (D) 𝐋𝐢𝐀𝐥𝐇

40. In the reaction given below, the total number of atoms having sp2 hybridization in the major
product P is ______. [JEE Adv -2021]

APNI KAKSHA 32
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
41 The major products A and B in the following set of reactions are: [JEE-MAINS 2021]

(A) (B)

(C) (D)

42. If the reaction sequence given below is carried out with 15 moles of acetylene, the amount of the
product D formed (in 𝐠 ) is______. [JEE Adv -2022]

The yields of A,B,C and D are given in parentheses.

[Given: Atomic mass of H = 1, C = 12, O = 16, Cl = 35]
43. The number of −𝐂𝐇𝟐 - (methylene) groups in the product formed from the following reaction
sequence is_______. [JEE Adv -2022]

44. The major products obtained from the reactions in List-II are the reactants for the named
reactions mentioned in List-I. Match List-I with List-II and choose the correct option.
[JEE Adv-2023]
List-I List-II
𝐙𝐧−𝐇𝐠,𝐇𝐂𝐥
(P) Etard reaction (1) Acetophenone →
(i) 𝐊𝐌𝐧𝐎𝟒 ,𝐊𝐎𝐇,𝚫
(Q) Gattermann reaction (2) Toluene →
(ii) 𝐒𝐎𝐂𝐥𝟐
𝐂𝐇𝟑 𝐂𝐥
(R) Gattermann-Koch reaction (3) Benzene →
anhyd. 𝐀𝐥𝐂𝐥𝟑

𝐍𝐚𝐍𝐎𝟐 /𝐇𝐂𝐥
(S) Rosenmund reduction (4) Aniline →
273-278 K
𝐙𝐧,𝚫
(5) Phenol ⟶
(A) 𝐏 → 𝟐; 𝐐 → 𝟒; 𝐑 → 𝟏; 𝐒 → 𝟑 (B) 𝐏 → 𝟏; 𝐐 → 𝟑; 𝐑 → 𝟓; 𝐒 → 𝟐
(C) 𝐏 → 𝟑; 𝐐 → 𝟐; 𝐑 → 𝟏; 𝐒 → 𝟒 (D) 𝐏 → 𝟑; 𝐐 → 𝟒; 𝐑 → 𝟓; 𝐒 → 𝟐

APNI KAKSHA 33
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
ANSWER KEY
EXERCISE # I
1. D 2. A 3. C 4. D 5. C 6. AC 7. A
8. C 9. B 10. AC 11. C 12. C 13. C 14. C
15. C 16. B 17. C 18. D 19. AC 20. D 21. D
22. C 23. C 24. C 25. A 26. B 27. B 28. D
29. A 30. C 31. C 32. B 33. ABCD 34. B 35. BC
36. AC 37. ABCD 38. BD 39. D 40. ABCD 41. C
EXERCISE # II
1. C 2. CD 3. D 4. ACD 5. ABC 6. ABCD 7. C
8. ACD 9. D 10. A 11. ABC 12. C 13. AB
14. (A)→P,R,S; (B)→Q; (C)→R,S; (D)→Q
15. 4 16. 4 17. A 18. B 19. A 20. BC 21. A
22. ABD 23. ABC

24.

25. (a) 𝐏𝐡– 𝐂𝐇𝟐 – 𝐂𝐇𝐎; (b) (C)

26. (i) Cis & trans 2-butene & 1-butene;

(ii)
(iii) Zero (Neo-pentane cannot be prepared by catalytic hydrogenation of alkene);
(iv) One

(v) Including optical = 4 , Excluding optical = 3

27.

APNI KAKSHA 34
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
28.

EXERCISE # III (MAIN & ADVANCE)

1. A 2. 3. D 4. A 5. A 6. B
7. B 8. D 9. B 10. D 11. D 12. A
13. C 14. A 15. C 16. A 17. B 18. 5
19. A 20. D 21. CD 22. C 23. A 24. B
25. A 26. B 27. B 28. C 29. B 30. B
31. A 32. B 33. C 34. B 35. A 36. B
37. B 38. D 39. B 40. 12 41. 0 42. 136
43. 0 44.

APNI KAKSHA 35
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
SOLUTION
EXERCISE # III (MAIN & ADVANCE)
18. M. wt 100 of ketone
So m, formula = 𝐂𝟔 𝐇𝟏𝟐 𝐎

(1 : 2 : 3 : 6 : 7 )

19.
Reduction of 𝐂𝐇𝟑 𝐂𝐎𝐎𝐇 will produce 𝐂𝐇𝟑 – 𝐂𝐇𝟐 – 𝐎𝐇(𝐀) Now reaction of 𝐂𝐇𝟑 – 𝐂𝐇𝟐 – 𝐎𝐇(𝐀)
with 𝐏𝐂𝐥𝟓 will produce 𝐂𝐇𝟑 – 𝐂𝐇𝟐 – 𝐂𝐥(𝐁). Now alcoholic KOH with Et–Cl will produce
𝐂𝐇𝟐 = 𝐂𝐇𝟐 (𝐂) Ethylene by 𝐄𝟐 elemination. Thus Ans. is (𝟏) Ethylene.
APNI KAKSHA 36
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
35.

36.

37. 𝐁𝟐 𝐇𝟔 is very selective and usually used to reduce acid to alcohol

38.

APNI KAKSHA 37
(ORGANIC CHEMISTRY) REDUCTION OXIDATION

39. 𝐁𝟐 𝐇𝟔 is very selective and usually used to reduce acid to alcohol.

40.

The total number of atoms having sp2 hybridization in the major product (P) = 12
This includes 4 C-atoms, 4 N-atoms and 4 O-atoms.

APNI KAKSHA 38
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
41.

42.

43.

APNI KAKSHA 39
(Organic Chemistry) Aldol Similar Name Reaction
HALOGENATION OF THE 𝛂-CARBON OF ALDEHYDES AND KETONES
(I) Acid-Catalyzed halogenation: -
When Br2 , Cl2 and I2 is added to an acidic solution of an aldehyde or a ketone, a halogen
replaces one of the α-hydrogens of the carbonyl compound. Halogenation takes place through
the slow formation of an enol followed by rapid reaction of the enol with the halogen.
Mechanism:

Step - I:

Step - II:

Step - III:

IInd Base-Catalyzed halogenation: - In the presence of excess base and excess halogen, a
methyl ketone is converted first into a trihalo-substituted ketone and then into a carboxylic
acid.

Mechanism:

APNI KAKSHA 1
(Organic Chemistry) Aldol Similar Name Reaction

Q.1 Identify the compounds which can show iodoform reaction and complete the reaction?

Q.2 Complete the following given reaction:

APNI KAKSHA 2
(Organic Chemistry) Aldol Similar Name Reaction
Q.3 Select the compound which does not show haloform reaction is/are:

(A) (B)

(C) Pyruvic acid (D)

Q.4

(𝐙) is:

(A) 𝐏𝐡 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝐎 (B)

(C) (D)

Q.5 Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by:
(A) I2 /NaOH (B) NaOH (C) NaCN/HCl (D) 2,4-DNP
Q.6 Which of the reagent is used to convert 2-Butanone into propanoic acid –
(A) NaOH, I2 /H + (B) Tollen's reagent (C) Fehling solution (D) NaOH, NaI/H +

Paragraph for Q.07 to Q.09

Q.7 Which one of the following reagent is best suitable for distinction between 𝑃1 and P2 –
(A) Braddy's reagent (2,4 DNP) (B) NaHSO3
(C) NaHCO3 (D) NaOH/I2
Q.8 Select the correct statement among the following -
(A) P1 will show aldol reaction & P2 will show cannizaro reaction
(B) P1 will show cannizaro reaction & P2 will show aldol reaction
(C) Both P1 &P2 will show cannizaro reaction
(D) Both P1 &P2 will show aldol reaction

APNI KAKSHA 3
(Organic Chemistry) Aldol Similar Name Reaction
Q.9 P2 ⎯⎯⎯⎯ ⎯
(i)conc.NaOH
( ii) H+
→ products

Select incorrect statement for the above reaction -

(A) It is a redox reaction
(B) It is a disproportion reaction
(C) Two products formed are alcohol & carboxylic acid
(D) It is an intramolecular reaction
Q.10 Which of the following will give yellow precipitate with NaOH/I2
(A) (B) CI3 CHO (C) (D) EtOH

Q.11

CaOCl2
W ⎯⎯⎯ →CHCl3 + Y
CaOCl2
X ⎯⎯⎯ →CHCl3 + Y
Y + Z ⎯⎯⎯⎯ Dry
Distillation
→Organicproduct ( s ) + CaCO3
Which of the following is major organic product
(A) CH3 − CHO (B) CH3 − CO − CH3
(C) CH3 − CH = CH − CH3 (D) HCHO
Q.12 Correct option regarding following reaction sequence.

(A) T is homologue of ' X ' (B) R is sodium salt of

(C) P can produce 𝐒 with NaOI (D) R is sodium salt of

Q.13 Which of the following compounds(s) give a sweet-smelling product having anesthetic use in
presence of Cl2 , NaOH, Δ.

(A) (B)

(C) (D)

APNI KAKSHA 4
(Organic Chemistry) Aldol Similar Name Reaction
Q.14 Reaction in which product can show positive haloform test :-
(A) CH3MgBr + PhCN ⎯⎯⎯
H O
→ (B) CH3 − CH2MgBr + Ph − COOEt ⎯⎯⎯
H O
→
3 3
(1 : 1)

(C) CH3MgBr + H − C − OMe ⎯⎯⎯ →

NH4Cl
(D) CH MgBr + H − C − OMe ⎯⎯⎯ →
(1:1) ||
3 NH4Cl
||
O O

Q.15 In which reaction haloform is obtained as one product: -

(A) Electrolysis of ethanolic aqueous solution of NaCl
(B) Isopropanol with bleaching powder
(C) Chlorination of methane in sun light
(D) Chloral is treated with NaOH
(2) ALDOL CONDENSATION
The 𝛂 − hydrogen of carbonyl compounds are acidic due to the fact that the anion (enolate ion)
is stabilized by resonance.

Base catalysed Aldol

In aqueous base, two acetaldehyde molecules react to form β-hydroxy aldehyde called aldol.
The reaction is called Aldol condensation. The enolate ion is the intermediate in the aldol
condensation of aldehyde and ketone. Acetaldehyde for instance, forms a dimeric product aldol
in presence of a dilute base (≈ 10%NaOH)

Mechanism:

APNI KAKSHA 5
(Organic Chemistry) Aldol Similar Name Reaction
Aldols are stable and may be isolated. They, however can be dehydrated easily by heating the
basic reaction mixture or by a separate acid catalyzed reaction. Thus if the above reaction is
heated the product is dehydrated to 2-butenal (crotonaldehyde).
Acid cataysed Aldol:
In acid catalysed aldol condensation enol form of carbonyl is the nucelophile in place of
enolate.
Mechanism:

Q.1 Write the product and mechanism for given reactions.

Q.2 Identify the intramolecular aldol product?

APNI KAKSHA 6
(Organic Chemistry) Aldol Similar Name Reaction
Q.3 Find out the total number of possible aldol products (including and excluding stereo products).
(I) C6H5 − CHO + CH3 − CHO ⎯⎯⎯⎯
NaOH/HOH
5ºC
→

(II) CH3 − CH = O + CH3 − CH2 − C − CH3 ⎯⎯⎯⎯

NaOH/HOH
5ºC
→
||
O
Q.4 Identify the structure of substrate?

Q.5 Complete reaction sequence:

Q.6 Complete the following reactions:

Q.7

(A) (B)

(C) (D)

APNI KAKSHA 7
(Organic Chemistry) Aldol Similar Name Reaction
Q.8 Consider following intramolecular aldol condensation reaction:

(A) (B)

(C) (D)

Q.9 Product 'E' is:

(A) (B)

(C) (D)

Q.10 Product '𝐘' formed in the given reaction is:

(A) (B) (C) (D)

Q.11 Product 'D' is:

(A) CH3 − CH2 − CH = CH2 (B) CH3 − CH2 − CH2 − CHO

(C) CH2 − CH2 − CH2 − COOH (D) CH2 = CH − CH = CH2
APNI KAKSHA 8
(Organic Chemistry) Aldol Similar Name Reaction
−

Q.12 CH3CH = CHCHO ⎯⎯→⎯⎯
OH
aldol
→ A, A is

(A) 𝐶𝐻3 (𝐶𝐻 = 𝐶𝐻)3 𝐶𝐻𝑂 (B) CH3 CH2 CH2 (CH = CH)2 CHO
(C) CH3 (CH2 CH2 )3 CH = CH − CHO (D) None is correct
Q.13 Which one of the following will undergo aldol reaction most readily.

(A) (B) (C) (D)

NaOH,  NaOH, 
Q.14 MeCHO ⎯⎯⎯ → A ⎯⎯⎯ → B; B is:
(A) Me(CH = CH)3 CHO (B) MeCH = CHCHO
(C) Me(CH = CH)2 − CHO (D) Me + (CH = CH)4 CHO
(3) CLAISEN CONDENSATION
Esters undergo SN AE Reaction. when attacked by a Nu− generated by the interaction of a base
(usually base related to the Alkoxy anion of ester) with one of the molecule of ester and this
Nu− attacks on another molecule. The reaction over all is considered as condensation of ester
known as claisen ester condensation.

Mechanism:

Sometimes, when two ester group are present within the molecule then the condensation
occurs intramolecule then cyclization caused thus is known as Dieckmann cyclization or
Dieckmann's condensation.

APNI KAKSHA 9
(Organic Chemistry) Aldol Similar Name Reaction
()i EtOK
Q.1 MeCOOEt ⎯⎯⎯⎯⎯
( ii ) Acidification→ A

()i MeOK
Q.2 EtCOOMe ⎯⎯⎯⎯⎯
( ii ) Acidification→ B

() i MeOK
Q.3 MeCOOMe + EtCOOMe ⎯⎯⎯⎯⎯
( ii ) Acidification→C

() 2 5 i C H ONa
Q.4 C6H5COOC2H5 + CH3COOC2H5 ⎯⎯⎯⎯⎯
( ii) Acidification→D + D'

Q.5

Q.6

Q.7

(4) PERKIN CONDENSATION

In Perkin reaction, condensation has been effected between aromatic aldehydes and aliphatic
acid anhydrides in the presence of sodium or potassium salt of corresponding acid of that
anhydride, to yield α, β - unsaturated aromatic acids.

APNI KAKSHA 10
(Organic Chemistry) Aldol Similar Name Reaction
Q.1

Q.2

Q.3

Q.4

(5) KNOEVENAGEL REACTION

Reaction of active methylene group with aldehyde & Ketones is known as knoevenagel
reaction.

High reactivity of the methylene group of the active methylene compound prevents self-
condensation of the aldehyde.

APNI KAKSHA 11
(Organic Chemistry) Aldol Similar Name Reaction
Q.1

Q.2

Q.3

Q.4

Q.5

Q.6

Q.7

Q.8

(6) MICHAEL ADDITION

Michael Addition: α − β unsaturated carbonyl compound undergo michael reaction with
compounds having active methylene. Many different nuclephile can add to α − β
unsaturated carbonyl compound. When the nucleophile is an enolate the addition reaction has
a special name MICHAEL REACTON.
APNI KAKSHA 12
(Organic Chemistry) Aldol Similar Name Reaction
Mechanism:

Q.1

Q.2

Q.3

Q.4

Q.5

(7) REFORMATSKY REACTION

α-halo esters when treated with Zn in gives organometallic halo ester which provides the
attacking Nu− for the another reactant, which is a carbonyl compound. When Nu− attacks on
carbonyl compound it gives an intermediate which upon acidic hydrolysis followed by heating,
results in formation of α, β - unsaturated acid. The overall reaction is known as Reformatsky
reaction.

APNI KAKSHA 13
(Organic Chemistry) Aldol Similar Name Reaction

Q.1 C6H5COCH3 + BrCH2COOEt ⎯⎯⎯1.Zn

⎯
2.H O ,
→A
3

Q.2

Q.3

Q.4

Q.5

Q.6

APNI KAKSHA 14
(Organic Chemistry) Aldol Similar Name Reaction

Q.7

Q.8 Matrix Match:

Match the column-
Column – I Column – II

(A) (P) Perkin's reaction.

(B) (Q) Reformatskii reaction.

( ) 31 CH COONa/ 
(C) Ph − CHO + CH3COOCOCH3 ⎯⎯⎯⎯⎯
(2) H O / 
→ (R) Product is a carboxylic acid with
3

aromatic ring within the same

molecule.

(D) (S) Double bond equivalent of the

product formed is less than or equal to

8.
(T) The major product cannot show
optical isomerism
(8) CANNIZARO REACTION
This reaction is given by aldehyde having no α - hydrogen in the presence of conc. NaOH/Δ or
KOH/Δ.

Mechanism:

In the presence of a very strong concentration of alkali, aldehyde first forms a doubly charged
anion (I) from which a hydride anion is transferred to the second milecule of the aldehyde to
form acid and an alkoxide ion. Subsequently, the alkoxide ion acquires a proton from the
solvent.
APNI KAKSHA 15
(Organic Chemistry) Aldol Similar Name Reaction

Q.1 Which of following will not undergo Cannizaro reaction

(A) (B)

(C) (D) Cl3 C − CHO

Q.2

Product (C) & (D) are:

(A) Ph − CO2 H, Ph − OH (B) Ph − CO−
2 , HCO2
−

(C) Ph − CH2 OH, H − CO2− (D) Ph − CO−

2 , CH3 OH
Q.3

(A) H2 C = CH − CO2 H (B)

(C) (D) H2 C = C = O

APNI KAKSHA 16
(Organic Chemistry) Aldol Similar Name Reaction
Q.4 (i) HCHO ⎯⎯⎯
NaOD

→ (ii) DCHO ⎯⎯⎯
NaOD

→
 18 
Q.5 (i) Ph − CHO ⎯⎯⎯→
OD/DOD

(ii) Ph − CHO ⎯⎯⎯
OH

→

Q.6 (i) Ph − CHO + HCHO ⎯⎯

KOH

→ (ii)

Q.7 (i) MeCH2 − CHO ⎯⎯

KOH

→ (ii) Me2CH − CHO ⎯⎯⎯⎯
conc.KOH

→
Q.8 (i) Me − NO2 + HCHO ⎯⎯→
KOH
(ii) MeCHO − HCHO ⎯⎯→
KOH
( excess ) ( excess )
+
Q.9 PhCOCHBr2 ⎯⎯⎯
Aq.OH
→ A ⎯⎯⎯
Conc.OH
→ B ⎯⎯
H
→ ;the compound ' 𝐂 ' is:
(A) PhCH(OH)CHO (B) PhCH(OH)COOH
(C) PhCOOH (D) None of these
Q.10 Matrix Match:
Match the column-
Column – I Column – II
(A) HCHO + NaOD (conc.) (P) DCOO− + CDH2 OH
(B) DCHO + NaOH (conc.) (Q) DCOO− + CD2 OH
(C) DCDO + NaOH (conc.) (R) DCOO− + CDH2 OD
(D) DCHO + NaOD (conc.) (S) HCOO− + CH3 OD

Q.11

(A) (B) (C) (D)

Q.12

(A) (B) (C) (D)

Q.13 The Cannizaro reaction of PhCOCHO forms the product(s)

(A) PhCOCH2 OH + PhCOCO2− (B)

(C) PhCO2− + PhCOCH2 OH (D) Both (A) and (C)

APNI KAKSHA 17
(Organic Chemistry) Aldol Similar Name Reaction

Q.14 Product is:

(A) (B)

(C) (D)

Q.15

True about this reaction is / are

(A) Cannizaro name is associated with this reaction
(B) It is a disproportion reaction
(C) It is a bimolecular reaction in r.d.s.
(D) All of these

Q.16

End product (B) of above reaction is:

(A) (B) (C) (D)

Q.17 The major product pair of the following reaction will be:

(A) (B)

(C) (D)

APNI KAKSHA 18
(Organic Chemistry) Aldol Similar Name Reaction
Q.18 Reactant 'X' will be:

(A) (B)

(C) (D)

(9) BENZIL-BENZILIC REARRANGEMENT OR BENZILIC ACID REARRANGEMENT

The base catalysed reaction of 1,2-diketones to a salt of -2-hydroxy carboxylic acid is known as
Benzilic acid rearrangement, this reaction is mainly applicable when aryl group is present on
both carbonyl carbons.

Mechanism:

Q.1

Q.2

APNI KAKSHA 19
(Organic Chemistry) Aldol Similar Name Reaction

Q.3

Q.4

Q.5

Q.6 Ph − CHO ⎯⎯
KCN

→P1 ⎯⎯⎯
Fenton's
Reagent
→P2 ⎯⎯⎯
NaOH
(2)H+
→P3

(10) TISCHENKO REACTION /CONDENSATION

(1) This reaction takes place between two molecules of aldehydes.
(2) Reaction is catalysed by aluminimum ethoxide.
(3) This is a two-step reaction, i.e., redox reaction followed by ester formation. Thus, this
reaction is extension of Cannizzaro reaction.

Mechanism:

(C H O) Al
Q.1 CH3 − CHO ⎯⎯⎯⎯
2 5 3

→?
(C H O) Al
Q.2 CH3 − CH2 − CHO ⎯⎯⎯⎯
2 5 3

→?
(C H O) Al
Q.3 OHC − CH2 − CH2 − CH2 − CHO ⎯⎯⎯⎯
2 5 3

→?
( C H O) Al
Q.4 CH3CHO + CH3 − CH2 − CHO ⎯⎯⎯⎯
2 5 3

→?
(11) COREY HOUSE SYNTHESIS
Reaction of Gilman's reagent with alkyl halide gives alkane as one of the product which is
known as Corey House synthesis,

APNI KAKSHA 20
(Organic Chemistry) Aldol Similar Name Reaction

To obtained good yield of alkane, the alkyl halide R′ − X must be either a methyl halide, a
primary alkyl halide, or a secondary cycloalkyl halide. (Best CH3 X, if possible) Preparation of
Gilman reagent:
→R2Cu LI
Cu − X,  
R − X ⎯⎯→
2Li
− LiX
RLi ⎯⎯⎯ − LiX
(2mole) Gilmanreagent
(alkylLithium)

Complete the following reaction sequence:

Q.1 CH3 − I ⎯⎯Li

Et2O
→( A ) ⎯⎯
Cul

→(B) ⎯⎯⎯⎯⎯⎯ 
→(C)
CH3CH2CH2CH2CH2I

CH3CH2CH2CH2Br ⎯⎯Li
Et2O
→(D) ⎯⎯
Cul

→(E) ⎯⎯⎯⎯⎯⎯
CH3CH2CH2CH2CH2Br

→(F )
Q.2 ( A ) ⎯⎯
Cl
2
h
→ ( B) ; ( B) ⎯⎯→(C)
Li

CH3Cl
(C) ⎯⎯ → ( D)
CuCl

; ( D) CH3 − CH − CH2 − CH3
 |
CH3

( ii ) CuBr,→ ( A ) ⎯⎯⎯ → ( B)
() i Li CH3 −Cl
Q.3 CH3 − CH2 − Br ⎯⎯⎯⎯ 

Q.4

Q.5

Q.6 How can you prepare following compounds using corey house synthesis.

(i) (ii) CH2 = CH − CH2 − CH3 (iii)

14
Q.7 (CH3 )2 CuLi + CH2 = CH − C H2 − Cl →
Q.8

Q.9

Q.10

APNI KAKSHA 21
(Organic Chemistry) Aldol Similar Name Reaction
Q.11 Which of the combination of Gilman's reagent & alkylhalide will be most suitable for
preparation of following compounds.

(i) CH3 − CH2 − CH3 (ii) (iii)

(iv) (v)

Q.12 Identify the product of following reactions:

(a) (b)

(12) BENZOIN CONDENSATION

The Benzoin Condensation is a coupling reaction between two aldehyades that allows the
preparation of 𝜶-hydroxyketones.

Mechanism of Benzoin Condensation

A strong base is now able to deprotonate at the former carbonyl C-atom.

A second equivalent of aldehyde reacts with this carbanion, elimination of the catalyst
regenerates the carbonyl compound at the end of the reaction

APNI KAKSHA 22
(Organic Chemistry) Aldol Similar Name Reaction
ANSWER KEY
(1) HALOGENATION OF THE 𝜶-CARBON OF ALDEHYDES AND KETONES
Q.1 (1,2,5,7,9,11)

Q.2 (i) (ii) CH3 − COO− + CHI3

(iii) (iv)
Q.3 (A, B)
Q.4 (C)
X: PhCH2 CH2 OH Y: PhCH2 CHO

Q.5 (A) Q.6 (A)

Q.7 (B)

(A) Both ketone & aldehyde react with braddy's reagent

2, 4 dinitrophenyl hydrazine.
(B) With NaHSO3 only aldehyde give crystalline bisulphite adduct whereas hindered ketone is
unable react.
(C) NaHCO3 will not react any of them.
(D) Both P1 &P2 are unable to form idoform with NaOH/I2
Q.8 (A)

For aldol 𝛼H should be present i.e. 𝑃1 where as 𝑃2

Will give cannizaro's as there is no. 𝛼H in P2.

Q.9 (D)

The above reaction is intermolecular redox reaction. In which desprotionation is taking place
as a result of which 2 different products are formed from singlet reactant.
APNI KAKSHA 23
(Organic Chemistry) Aldol Similar Name Reaction
Q.10 (A,B,C,D)

Q.11

Q.12 (A, B, C)

Q.13 (A, B, D)

Q.14 (A, B, C, D)
Q.15 (A, B, C, D)
(2) ALDOL CONDENSATION

Q.1

APNI KAKSHA 24
(Organic Chemistry) Aldol Similar Name Reaction

Q.2

Q.3

Q.4

Q.5

Q.6

APNI KAKSHA 25
(Organic Chemistry) Aldol Similar Name Reaction
Q.7 (C)
Intramolecular aldol condensation the 1,4-additon and finally clemmesion reduction.
Q.8 (D)
Q.9 (D)

Q.10 (B)
Ozonolysis followed by intramolecular aldol.
Q.11 (C)

Q.12 (A)
Q.13 (A)
Q.14 (A)

(3) CLAISEN CONDENSATION

Q.1

Q.2

APNI KAKSHA 26
(Organic Chemistry) Aldol Similar Name Reaction

Q.3 4 products

Q.4

Q.5

Q.6

(4) PERKIN CONDENSATION

Q.1

Q.2

Q.3

Q.4 CH3 COOCOCH3

(5) KNOEVENAGEL REACTION
Q.1 Q.2

Q.3 HOOC − CH = CH − COOH Q.4

Q.5 Ph − CH = CH − NO2 Q.6

APNI KAKSHA 27
(Organic Chemistry) Aldol Similar Name Reaction
Q.7

Q.8

(6) MICHAEL ADDITION

Q.1 Q.2

Q.3 Q.4

Q.5

(7) REFORMATSKY REACTION

Q.1 Q.2

Q.3 Q.4

APNI KAKSHA 28
(Organic Chemistry) Aldol Similar Name Reaction

Q.5 Q.6

Q.7

Q.8 (A)-RST, (B) -Q,R,S,T (C)-P,R,S,T (D) R,T

(8) CANNIZARO REACTION

Q.1 (D) As Cl3 C − CHO given chloroform
Q.2 (C) In cross cannizzaro reaction move reactive carbonyl compound is oxidised & less in
reduced.
Q.3 (B) Intramolecular cannizzaro followed by heating effect
Q.4 (i) CH3 OD + HCOONa (ii) DCH2 OD + DCOONa
Q.5 (i) PhCH2 OD + PhCOONa (ii) Ph − CH2 OH + PhCOONa
Q.6 (i) Ph − CH2 OH + HCOOK (ii)

Q.7 (i) (ii) Me2 CH − CH2 OH + Me2 CHCOOK

Q.8 (i) (ii)

Q.9 (B)

Q.10 (A) → S; (B) → P; (C) → Q; (D) → R

Q.11 (A)

APNI KAKSHA 29
(Organic Chemistry) Aldol Similar Name Reaction
Q.12 (D)

Q.13 (B)
Q.14 (C)

Q.15 (A)

option A is correct.
Q.16 (B)

Q.17 (B) Cross cannizaro reaction

Q.18 (A)

(9) BENZIL-BENZILIC REARRANGEMENT OR BENZILIC ACID REARRANGEMENT

Q.1 Q.2

Q.3

APNI KAKSHA 30
(Organic Chemistry) Aldol Similar Name Reaction

Q.4 Q.5

Q.6

(10) TISCHENKO REACTION/CONDENSATION

Q.1 Q.2

Q.3 Q.4 4 products

(11) COREY HOUSE SYNTHESIS

Q.1 (A) CH3 Li, (B) (CH3 )2 CuLi,
(C) CH3 − CH2 CH2 CH2 CH2 CH3 , (D) CH3 CH2 CH2 CH2 Li,
(E) (CH3 CH2 CH2 CH2 )2 CuLi, (F) CH3 CH2 CH2 CH2 − CH2 CH2 CH2 CH2 CH3
Q.2

Q.3 (A) [CH3 CH2 ]⊖

2 CuLi
⊕
(B) CH3 − CH2 − CH3

Q.4

Q.5

APNI KAKSHA 31
(Organic Chemistry) Aldol Similar Name Reaction
Q.6

14
Q.7 CH3 − CH2 − CH = CH2
Q.8 not available

Q.9

Q.10

Q.11

Q.12

APNI KAKSHA 32