CBSE

Class 12 Chemistry
Important Questions
Haloalkanes and Haloarenes

Conceptual Questions

1. Why haloalkanes are more reactive than haloarenes.

Ans.
i. In haloarenes, there is double bond character b/w carbon and halogen due to
resonance effect which makes him less reactive.

ii. In benzene, carbon being sp2 hybridised which is smaller in size than sp3 present in
haloalkanes. So C-Cl bond in aryl halides is shorter and stronger.
2. Why do haloalkenes under go nucleophillic substitution whereas haloarenes under
go electophillic substitution.
Ans. Due to more electro negative nature of halide atom in haloalkanes carbon atom
becomes slightly positive and is easily attacked by nucleophillic reagents.
While in haloarenes due to resonance, carbon atom becomes slightly negative and
attacked by electrophillic reagents.
3. When an alkyl halide is treated with ethanolic solution of KCN, the major product is
alkyl cyanide where as if alkyl halide is treated with AgCN,the major product is
alkyl isocyanide.
Ans. KCN is ionic they can attach through C or N but C-C bond is strong than C-N bond. So
alkyl cyanide is the major product but AgCN is covalent so more electronegative N can
attach to C and forms isocyanides.

4. How do 10 20 30 alcohols differ in terms of dehydrogenation?

Ans.

5. Why are the reaction of alcohol /phenol with acid chloride in the presence of
pyridine?
Ans. Because esterification reaction is reversible and presence of base (pyridine)
nuetralises HCl produced during reaction thus promoting forward reaction.

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 6. Explain why o-nitrophenol is more acidic than o-methoxy phenol?
Ans. -NO2 group is electron with - drawing group, e- density on O decreases and loss of

H+ is easy whereas –OCH3 group is electron releasing group , which increases e- density

on O , which makes difficult to the loss of H+, hence are less acidic.
7. Aryl halides cannot be prepared by the action of sodium halide in the presence
H2SO4. Why?

Ans. Due to resonance the carbon- oxygen bond in phenols has partial double bond and it
is stronger than carbon oxygen single bond.
8. Why Grignard reagent should be prepared under an hydrous conditions.?
Ans. Grignard reagent react with H2O to form alkanes , therefore they are prepared

under anhydrous condition.

9. Why is Sulphuric acid not used during the reaction of alcohols with KI?
Ans. It is because HI formed will get oxidized to I2 by concentrated Sulphuric acid which
is an oxidizing agent.
10. p- dichlorobenzene has highest m.p. than those of ortho and m-isomers?
Ans. p- dichlorobenzene is symmetrical, fits into crystal lattice more readily and has
higher melting point.
11. Although chlorine is an electron- withdrawing group, yet it is ortho and para
directing in electrophillic aromatic substitution reactions.Why?
Ans. Chlorobenzene is resonance hybrid, there is –ve charge at 0 and para positions,
electrophilic substitution reaction will take place at 0 and para position due to +R effect.
+R effect is dominating over – I effect.

12. The treatment of alkyl chlorides with aqueous KOH lead to the formation of alcohols
but in presence of alcoholic KOH alkenes are major products. Explain?
Ans. In aqueous KOH,OH- is nucleophile which replaces another nucleophile.
R-X +KOH → R-OH +KX Where as in alcoholic KOH
C2H5OH +KOH → C2H5O- + K+

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 CH3CH2-Cl + alcoholic KOH CH2 =CH2 + C2H5OH

13. Explain why vinyl chloride is unreactive in nucleophillic substitution reaction?

Ans. Vinyl chloride is unreactive in nucleophillic substitution reaction because of double
bond character between C=CL bond which is difficult to break.

14. Arrange the following compounds according to reactivity towards nucleophillic

substitution reaction with reagents mentioned :-
(i) 4- nitro chloro benzene, 2,4 di nitro chloro bemzene, 2,4,6, trinitrochlorobenzene
with CH3ONa

Ans- 2,4,6, trinitrochlorobenzene > 2,4 dinitrochlorobemzene > 4- nitrochlorobenzene

15. Which compound will react faster in SN2 reaction with OH-?

Ans-
a. CH3Br and CH3I (SN2)

CH3I will react faster than CH3Br

b. (CH3)3C-Cl or CH3Cl (SN2)

CH3Cl will react faster than 30 halide

16. Arrange in order of boiling points.

a. Bromobenzene, Bromoform, chloromethane,Dibromo-methane
b. 1-chloropropane, Isopropyle chloride, 1-Chlorobutane.
Ans.
a. chloromethane < Bromobenzene < Dibromo-methane < , Bromoform
b. Isopropyle chloride <1-chloropropane <1-Chlorobutane
(As Branching increases , boiling point decreases)
17. Predict the reactivity in SN1

C6H5CH2Br, C6H5CH (C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)( C6H5)Br

Ans. 30 > 20> 10 (SN1)

C6H5C(CH3)(C6H5)Br > C6H5(C6H5)Br > C6H5CH(CH3)Br > C6H5CH2Br (30) (20) (20) (10)

18. Which compound undergoes SN1 reaction first?

Ans.
1.

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 2. (20)

SHORT ANSWER TYPE QUESTIONS 3 MARKS QUESTIONS

1. How can we produce nitro benzene from phenol?

Ans.
I. First convert phenol to benzene by heating with Zn dust.
II. Nitration of benzene with conc. nitric acid in presence of conc. sulphuric acid.
2. Alcohols reacts with halogen acids to form haloalkenes but phenol does not form
halobenzene. Explain.
Ans. The C-O bond in phenol acquires partial double bond character due to resonance
and hence be cleared by X- ions to form halobenzenes. But in alcohols a pure C — O bond
is maintained and can be cleared by X– ions.
3. Explain why o-nitrophenol is more acidic than o-methoxy phenol?
Ans. Due to — R and — I effect of — NO2 group, e– density on =O‘ if O — H bond

decreases and loss of H+ is easy.– I effect In contrast, in o-methoxy phenol due to + R

effect, – OCH3 increases. e– density on O2 of O—H group, and hence loss of H+ is difficult.

(both –ve charge repel each other)

4. Of benzene and phenol, which is more easily nitrated and why?
Ans. Nitration is an electrophilic substitution. The –OH group in phenol increases the
electron density at ortho and para position as follows Since phenol has higher electron
density due to electron releasing nature of -OH group, compared to benzene , therefore
nitration is easy in phenol than benzene.
5. How will you account for the following? Ethers possess a net dipole moment even if
they are symmetrical in structure?
Ans. A. Because of greater electronegativity of o- atom than carbon C – O bonds are polar.

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 C – O bond are inclined to each other at an angle of 110° (or more), two dipoles do not
cancel out each other.
6. How do 1°, 2° and 3° alcohols differ in terms of their oxidation reaction and
dehydrogenation?
Ans.
I. Oxidation reaction : (O) (O)
1° alcohol → aldehyde → carboxylic acid (O) (O)
2° alcohol→ ketone → carboxylic acid (acid with loss of 1 carbon atom) (O)
3° alcohol→ resistant to oxidation
II. Hydrogenation reaction : give
1° alcohol → aldehyde
2° alcohol → ketone
3° alcohol → alkene 3° alcohols prefer to undergo dehydration and form alken
7. How is diethyl ether prepared from ethyl alcohol?
Ans. Ethyl alcohol is first treated with sodium to form sodium ethoxide

C2H5OH + Na C2H5O– Na+ + H2

Sodium ethoxide is then treated with ethyl halide to form di ethyl ether. SN²

C2H5O Na+ — C2H5X → C2H5O C2H5 + NaX (Williamson synthesis)

II. Complete the reaction:

(a) CH3OCH3 + PCl5?

(b) C2H5OCH3 + HCl?

(c) (C2H5)2 O + HCl

(a) 2 CH3Cl

(b) CH3Cl + C2H5OH

(c) C2H5Cl + C2H5OH

8. Why are reactions of alcohol/phenol and with acid chloride in the presence of
pyridine?
Ans. Because esterification reaction is reversible and presence of base (pyridine)
neutralises HCl produced during reaction thus promoting forward reaction.

LONG ANSWER TYPE QUESTIONS

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1. How the following conversions can be carried out?
i. Propene to propan-1-ol
ii. 1-Bromopropane to 2-bromopropane
iii. Toluene to benzyl alcohol
iv. Benzene to 4-bromonitrobenzene
v. Benzyl alcohol to 2-phenylethanoic acid
Ans.
i.

ii.

iii.

iv.

v.

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2. How the following conversions can be carried out?
i. Ethanol to propanenitrile
ii. Aniline to chlorobenzene
iii. 2-Methyl-1-propene to 2-chloro-2-methylpropane
iv. Ethyl chloride to propanoic acid
Ans.
i.

ii.

iii.

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 iv.

3. How the following conversions can be carried out?

i. But-1-ene to n-butyliodide
ii. 2-Chloropropane to 1-propanol
iii. Isopropyl alcohol to iodoform
iv. Chlorobenzene to p-nitrophenol
v. 2-Bromopropane to 1-bromopropane
Ans.
i.

ii.

iii.

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 iv.

v.

4. How the following conversions can be carried out?

i. Chloro ethane to butane
ii. Benzene to diphenyl
iii. tert-Butyl bromide to isobutyl bromide
iv. Aniline to phenylisocyanide
Ans.
i.

ii.

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 iii.

iv.

Conceptual Question

1. Preparation of ethers by acid dehydration of secondry or 30 alcohols is not a

suitable method?
Ans. The formation of ethers by dehydration of alcohol is a bimolecular reaction (SN2)

group is hindered. as a result elimination dominates substitution as 30 carbocation is

more stable. Hence in place of others, alkenes are formed.

2. Phenols do not give protonation reactions readily. Why?

Ans. The lone pair on oxygen of O-H in phenol is being shared with benzene ring through
resonance. Thus, lone pair is not fully present on oxygen and hence phenols do not
undergo protonation reactions.
3. Ortho- nitrophenol is more acidic than ortho –methoxy phenol? why?
Ans. NO2 group is electron with drawing which increases acidic character due to easily

ease

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REASONING QUESTIONS

1. Explain why propanol has higher boiling point than that of the hydrocarbon,
butane?
Ans. The molecules of Butane are held together by weak van der Waal‘s Forces of
attraction while those of propanol are held together by stronger intermolecular hydrogen
bonding.
2. Alcohols are comparatively more soluble in water than hydrocarbons of
comparable molecular masses. Explain this fact.
Ans. Alcohols can form hydrogen bonds with water and break the hydrogen bonds
already existing between water molecules Therefore they are soluble in water. Whereas
hydrocarbons cannot form hydrogen bonds with water and hence are insoluble in water.
3. While separating a mixture of ortho and para nitrophenols by steam distillation,
name the isomer which will be steam volatile. Give reason.
Ans. O-nitrophenol is steam volatile due to intramolecular hydrogen bonding and hence
can be separated by steam distillation from pnitrophenol which is not steam volatile
because of inter-molecular hydrogen bonding.
4. Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?

Ans. The nitro-group is an electron-withdrawing group. The presence of this group in the
ortho position decreases the electron density in the O-H bond. As a result, it is easier to
lose a proton. Also,the o-nitrophenoxide ion formed after the loss of proton is stabilized
by resonance. Hence,ortho-nitrophenol is stronger acid. On the other hand, methoxy
group is an electron-releasing group. Thus ,it increases the electron density in the O-H
bond and hence, the proton cannot be given out easily. Therefor ortho-nitrophenol is
more acidic than ortho- methoxyphenol.
5. Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a
suitable method. Give reason.
Ans. The formation of ethers by dehydration of alcohol is a bimolecular reaction (SN)2

involving the attack of an alcohol molecule on a protonated alcohol molecule. In the

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 method, the alkyl group should be unhindered. In case of secondary or tertiary alcohols,
the alkyl group is hindered. As a result, elimination dominates substitution.
6. What is meant by hydroboration-oxidation reaction? Illustrate it with an example.
Ans. Diborane (BH3)2 reacts with alkenes to give trialkyl boranes as addition product.

This is oxidised to alcohol by hydrogen peroxide in the presence of aqueous sodium

hydroxide.

7. Give the equations of reactions for the preparation of phenol from cumene.
Ans.

8. Write chemical reaction for the preparation of phenol from chlorobenzene.

Ans. Chlorobenzene is fused with NaOH at 623K and 320 atmospheric pressure. Phenol is
obtained by acidification of sodium phenoxide so produced.
9. How is aspirin (Acetylsalicylic acid) prepared from salicylic acid? Ans. Acetylation
of salicylic acid produces aspirin.
Ans.

10. Which out of propan-1-ol and propan-2-ol is stronger acid?

Ans. Propan-1-ol is stronger acid than propan-2-ol. The acidic strength of alcohols is in
the order 10>20>30.
11. What is denaturation of an alcohol?

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 Ans. The commercial alcohol is made unfit for drinking by mixing in it some copper
sulphate (to give it a colour) and pyridine (a foul smelling liquid). It is known as
denaturation of alcohol.
12. Give IUPAC name of CH3OCH2OCH3

Ans. Dimethoxymethane
13. Diethyl ether does not react with sodium. Explain.
Ans. Diethyl ether does not contain any active hydrogen.

SHORT ANSWER TYPE QUESTIONS 2 MARKS QUESTIONS

1. Give two reactions that show the acidic nature of phenol. Compare acidity of phenol
with that of ethanol.
Ans. The acidic nature of phenol can be represented by the following two reactions: (i)
Phenol reacts with sodium to give sodium phenoxide, liberating H2.

Phenol reacts with sodium hydroxide to give sodium phenoxide and water as by-products

The acidity of phenol is more than that of ethanol. This is because after losing a proton,
the phenoxide ion undergoes resonance and gets stabilized whereas ethoxide ion does
not.
2. How does phenol react with dilute and conc. HNO3?

Ans.
i. With dilute nitric acid at low temperature (298 K), phenol yields a mixture of ortho
and para nitrophenols.

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 ii. With concentrated nitric acid, phenol is converted to 2,4,6-trinitrophenol. The product
is commonly known as picric acid.

3. How does phenol react with Br2 in CS2 and Bromine water?

Ans.
i. When the reaction is carried out in solvents of low polarity such as CHCl3 or CS2 and

at low temperature, monobromophenols are formed.

ii. When phenol is treated with bromine water, 2,4,6- tribromophenol is formed as white
precipitate.

4. How do you account for the fact that unlike phenol, 2, 4- dinitrophenol and 2, 4, 6-
trinitrophenol are soluble in aqueous solution of sodium carbonate?
Ans. 2, 4-Dinitrophenol and 2, 4, 6-trinitrophenol are stronger acids then carbonic acid
(H2CO3) due to the presence of electron withdrawing – NO2 groups. Hence, they react

with Na2CO3 to form their corresponding salts and dissolve in aq. Na2CO3 solution.

5. i. Why is the Dipole moment of methanol higher than that of phenol?

ii. Explain why phenols do not undergo substitution of the –OH group like alcohols.

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 Ans.
i. Due to electron withdrawing effect of phenyl group, the C— O bond in phenol is less
polar, whereas in case of methanol the methyl group has electron releasing effect and
hence C—O bond in it is more polar.
ii. C—O bond in phenols has partial double bond character due to resonance and hence
is difficult to cleave.
6. Account for the following
a. Boiling point of the C2H5OH is more than that of C2H5Cl

b. The solubility of alcohols in water decreases with increase in molecular mass.

Ans.
a. Because of hydrogen bonding.
b. With increase in molecular mass the non-polar alkyl group becomes more
predominant.
7. Answer the following
a. What is the order of reactivity of 10, 20 and 30 alcohols with sodium metal?
b. How will you account for the solubility of lower alcohols in water?
Ans.
a. 10>20>30.
b. Here—OH group is predominant and the alcohol molecules can form hydrogen bonds
with water molecules.
8. Give reasons:
i. Nitration of phenol gives ortho- and para- products only.
ii. Why do alcohols have higher boiling points than the haloalkanes of the same
molecular mass?
Ans.
i. -OH group increases the electron density more at ortho and para positions through its
electron releasing resonance effect.
ii. Alcohols are capable of forming intermolecular H-bonds.
9. Account for the following:
i. Phenols has a smaller dipole moment than methanol
ii. Phenols do not give protonation reactions readily.
Ans.
i. In phenol the electron withdrawing inductive effect of –OH group is opposed by

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 electron releasing the resonance effect of –OH.
ii. The lone pair on oxygen of –OH in phenol is being shared with benzene ring through
resonance. Thus, lone pair is not fully present on oxygen and hence phenols do not
undergo protonation reactions.
10. Explain the fact that in aryl alkyl ethers
i. The alkoxy group activates the benzene ring towards electrophilic substitution
and
ii. It directs the incoming substituents to ortho and para positions in benzene ring.
Ans.

i.

In aryl alkyl ethers, due to the +R effect of the alkoxy group, the electron density in
the benzene ring increases as shown in the following resonance structure.

Thus, benzene is activated towards electrophilic substitution by the alkoxy group.

ii. It can also be observed from the resonance structures that the electron density
increases more at the ortho and para positions than at the meta position. As a result,
the incoming substituents are directed to the ortho and para positions in the benzene.

SHORT ANSWER TYPE QUESTIONS 3 MARKS QUESTIONS

1. How are primary, secondary and tertiary alcohols prepared from Grignard
Reagents?
Ans.

The reaction produces a primary alcohol with methanal, a secondary alcohol with other
aldehydes and tertiary alcohol with ketones.

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2. Give the equations of oxidation of primary, secondary and tertiary alcohols by Cu at
573 K.

Ans.

3. Give equations of the following reactions:

i. Oxidation of propan-1-ol with alkaline KMnO4 solution.
ii. Bromine in CS2 with phenol.

iii. Dilute HNO3 with phenol.

Ans.
i.

ii.

iii.

4. Show how will you synthesize:

i. 1-phenylethanol from a suitable alkene.
ii. (cyclohexylmethanol using an alkyl halide by an SN2 reaction.
iii. pentan-1-ol using a suitable alkyl halide?
Ans.

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 i. By acid-catalyzed hydration of ethylbenzene (styrene), 1- phenylethanol can be
synthesized.

ii. When chloromethylcyclohexane is treated with sodium hydroxide,

cyclohexylmethanol is obtained.

iii. When 1-chloropentane is treated with NaOH, pentan-1-ol is produced.

5. How are the following conversions carried out?

i. Propene → Propan-2-ol
ii. Benzyl chloride → Benzyl alcohol
iii. Ethyl magnesium chloride → Propan-1-ol.
Ans.
i. If propene is allowed to react with water in the presence of an acid as a catalyst, then
propan-2-ol is obtained.

ii. If benzyl chloride is treated with NaOH (followed by acidification) then benzyl alcohol
is produced.

iii. When ethyl magnesium chioride is treated with methanol, an adduct is the produced
which gives propan -1-ol on hydrolysis.

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6. Name the reagents used in the following reactions:
i. Oxidation of a primary alcohol to carboxylic acid.
ii. Oxidation of a primary alcohol to aldehyde.
iii. Bromination of phenol to 2,4,6-tribromophenol.
Ans.
i. Acidified potassium permanganate
ii. Pyridinium chlorochromate (PCC)
iii. Bromine water
7. How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this
reaction.
Ans. 1-propoxypropane can be synthesized from propan-1-ol by dehydration. Propan-1-ol
undergoes dehydration in the presence of protic acids (such as H2SO4, H3PO4) to give 1-

propoxypropane.

The mechanism of this reaction involves the following three steps:

Step 1: Protonation

Step 2: Nucleophilic attack

Step 3: Deprotonation

8. Write the equation of the reaction of hydrogen iodide with:

i. 1-propoxypropane
ii. Methoxybenzene and
iii. Benzyl ethyl ether

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 Ans.
i.

ii.

iii.

LONG ANSWER TYPE QUESTION 5 MARKS QUESTIONS

1. Write equations of the following reactions:

i. Friedel-Crafts reaction−alkylation of anisole.
ii. Nitration of anisole.
iii. Bromination of anisole in ethanoic acid medium.
iv. Friedel-Craft‘s acetylation of anisole.
v. Reaction of phenol with Zn dust.
Ans.
i.

ii.

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iii.

iv.

v.

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