CLASS 12 CHEMISTRY · CHAPTER 11 ALCOHOLS ONLY · NCERT Q&A

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Alcohol
Questions & Answers
!" Intext + Exercise · Alcohols section only · Ch. 11

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A LCOH OL O NLY

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In-Text Questions Q 11.1 – 11.7

11.1 Classify the following as primary, secondary and tertiary

alcohols:
(i) (CH₃)₃C–CH₂OH (ii) CH₂=CH–CH₂OH (iii) (C₆H₅)₂CHOH
(iv) (CH₃)₂CH–OH (v) C₆H₅–CH(OH)–CH₃ (vi) (CH₃)₂C(OH)–
CH=CH₂

ANSWER
 TYPE COMPOUNDS

Primary (1°) (i) (CH₃)₃C–CH₂OH, (ii) CH₂=CH–CH₂OH (allylic)

Secondary (iii) (C₆H₅)₂CHOH, (iv) (CH₃)₂CHOH, (v) C₆H₅–CH(OH)–

(2°) CH₃

Tertiary (3°) (vi) (CH₃)₂C(OH)–CH=CH₂

Allylic alcohols: (ii) and (vi) — the –OH is on sp³ carbon adjacent to C=C
double bond.

11.2 Name the following alcohols according to the IUPAC system:

(i) A branched chain compound with –Cl, 2 isopropyl groups,
–OH (pentan-1-ol derivative)
(ii) A hexane-1,3-diol with two methyl groups
(iii) 3-Bromocyclohexanol (iv) Hex-1-en-3-ol (v) 2-Bromo-
3-methylbut-2-en-1-ol

ANSWER

1. 3-Chloromethyl-2-isopropylpentan-1-ol

2. 2,5-Dimethylhexane-1,3-diol

3. 3-Bromocyclohexan-1-ol

4. Hex-1-en-3-ol

5. 2-Bromo-3-methylbut-2-en-1-ol

Rule reminder: Number the chain to give –OH the lowest locant. For diols
use -diol; for unsaturated alcohols, the chain must include both the
double bond and –OH carbons.
 11.3 Show how the following alcohols can be prepared from a
suitable Grignard reagent reacting with methanal (HCHO):
(i) 2-Methylpropan-1-ol (ii) Cyclohexylmethanol

ANSWER

When a Grignard reagent (RMgX) reacts with methanal (HCHO), a primary

alcohol is always formed after hydrolysis.

(i) (CH₃)₂CH–MgBr + HCHO → (CH₃)₂CH–CH₂–OH [Isopropyl MgBr

+ methanal → 2-Methylpropan-1-ol]

(ii) C₆H₁₁–MgBr + HCHO → C₆H₁₁–CH₂–OH [Cyclohexyl MgBr +

methanal → Cyclohexylmethanol]

Key: Methanal (formaldehyde) + RMgX always 1° alcohol. Identify the

R group from the product structure.

11.4 Write structures of the products of the following reactions:

(i) CH₃–CH=CH₂ + H₂O/H⁺
(ii) Cyclohexanone + NaBH₄
(iii) PhCHO (benzaldehyde) + NaBH₄

ANSWER

(i) CH₃–CH=CH₂ + H₂O/H⁺ → CH₃–CH(OH)–CH₃ [Propan-2-ol —

Markovnikov addition]

(ii) Cyclohexanone + NaBH₄ → Cyclohexanol (2° alcohol)

[NaBH₄ reduces C=O to C–OH; doesn't touch ester groups]

(iii) C₆H₅–CHO + NaBH₄ → C₆H₅–CH₂OH [Benzaldehyde → Benzyl

 alcohol, a 1° alcohol]

NaBH₄ is a mild reducing agent. It reduces aldehydes and ketones but

cannot reduce carboxylic acids or esters. Use LiAlH₄ for those.

11.5 Give structures of the products when the following alcohols

react with (a) HCl–ZnCl₂, (b) HBr, (c) SOCl₂:
(i) Butan-1-ol (ii) 2-Methylbutan-2-ol

ANSWER

(i) Butan-1-ol (1° alcohol):

(a) CH₃CH₂CH₂CH₂OH + HCl/ZnCl₂ →(heat) CH₃CH₂CH₂CH₂Cl + H₂O

[1° needs heating with Lucas reagent] (b) CH₃CH₂CH₂CH₂OH +
HBr → CH₃CH₂CH₂CH₂Br + H₂O (c) CH₃CH₂CH₂CH₂OH + SOCl₂ →
CH₃CH₂CH₂CH₂Cl + HCl + SO₂

(ii) 2-Methylbutan-2-ol (3° alcohol):

(a) (CH₃)₂C(OH)CH₂CH₃ + HCl/ZnCl₂ → immediately turbid →

(CH₃)₂CCl–CH₂CH₃ + H₂O (b) + HBr → (CH₃)₂CBr–CH₂CH₃ + H₂O
(c) + SOCl₂ → (CH₃)₂CCl–CH₂CH₃ + HCl + SO₂

Reactivity with Lucas: 3° immediate turbidity | 2° ~5 min | 1°

needs heating

11.6 Predict the major product of acid-catalysed dehydration of:

(i) 1-Methylcyclohexanol (ii) Butan-1-ol

ANSWER
(i) 1-Methylcyclohexanol:

1-Methylcyclohexanol + H₂SO₄/heat → 1-Methylcyclohexene

(major) [Saytzeff's rule: more substituted alkene is
preferred]

(ii) Butan-1-ol:

CH₃CH₂CH₂CH₂OH + H₂SO₄/443K → But-2-ene (major) + But-1-ene

(minor) [1° carbocation rearranges to 2° carbocation → but-
2-ene]

Saytzeff's rule: In elimination, the more substituted (more stable) alkene

is the major product.

11.7 Write the mechanism of hydration of ethene to yield ethanol.

ANSWER

Acid-catalysed hydration of ethene proceeds in 3 steps:

Step 1 — Protonation (electrophilic attack of H₃O⁺):

CH₂=CH₂ + H⁺ → CH₃–CH₂⁺ (ethyl carbocation) Step 2 —
Nucleophilic attack of water (slow, rate-determining): CH₃–
CH₂⁺ + H₂O → CH₃–CH₂–OH₂⁺ (oxonium ion) Step 3 —
Deprotonation (fast): CH₃–CH₂–OH₂⁺ → CH₃–CH₂–OH + H⁺
(ethanol)

Overall: CH₂=CH₂ + H₂O (H⁺ cat.) CH₃CH₂OH | Follows Markovnikov's

rule
EXERCISE
Exercise Questions Alcohol-related only

E1 Write IUPAC names of the following alcohols:

(i) (CH₃)₃C–CH(OH)–CH(CH₃)₂ (ii) A C₇ diol (5-ethylheptan-2,4-
diol)
(iii) CH₃CH(OH)CH(OH)CH₃ (iv) Glycerol (propane-1,2,3-triol)

ANSWER

1. 2,2,4-Trimethylpentan-3-ol

2. 5-Ethylheptan-2,4-diol

3. Butane-2,3-diol

4. Propane-1,2,3-triol (glycerol)

E2 Write structures for: (i) 2-Methylbutan-2-ol (ii) 1-

Phenylpropan-2-ol (iii) 3,5-Dimethylhexane-1,3,5-triol (iv)
Cyclohexylmethanol (v) 3-Cyclohexylpentan-3-ol

ANSWER

(i) CH₃–C(CH₃)(OH)–CH₂CH₃ [3° alcohol] (ii) C₆H₅–CH₂–

CH(OH)–CH₃ [2° benzylic alcohol] (iii) HOCH₂–C(CH₃)(OH)–
CH₂–CH(CH₃)–CH₂–C(CH₃)(OH)H [Triol] (iv) C₆H₁₁–CH₂OH
[Primary, cyclohexyl ring] (v) C₂H₅–C(OH)(C₆H₁₁)–C₂H₅ [3°
alcohol]
 E3 (i) Draw all isomeric alcohols of molecular formula C₅H₁₂O and
give their IUPAC names.
(ii) Classify them as primary, secondary, or tertiary.

ANSWER — 8 ISOMERS OF C₅H₁₂O

# IUPAC NAME TYPE

a Pentan-1-ol — CH₃(CH₂)₄OH 1°

b 3-Methylbutan-1-ol — (CH₃)₂CHCH₂CH₂OH 1°

c 2-Methylbutan-1-ol — CH₃CH₂CH(CH₃)CH₂OH 1°

d 2,2-Dimethylpropan-1-ol — (CH₃)₃CCH₂OH 1°

e Pentan-2-ol — CH₃CH(OH)CH₂CH₂CH₃ 2°

f 3-Methylbutan-2-ol — CH₃CH(OH)CH(CH₃)₂ 2°

g 2-Methylbutan-2-ol — (CH₃)₂C(OH)CH₂CH₃ 3°

h Pentan-3-ol — CH₃CH₂CH(OH)CH₂CH₃ 2°

Primary: a, b, c, d | Secondary: e, f, h | Tertiary: g

E4 Explain why propanol has a higher boiling point than butane,

despite butane having higher molecular mass.

ANSWER

Boiling point depends on the strength of intermolecular forces.

Butane (C₄H₁₀): molecules are held by weak van der Waals forces only,
easily overcome low boiling point (272 K)

Propanol (C₃H₇OH): molecules are held by strong intermolecular

 hydrogen bonds (O–H···O), requiring much more energy to break higher
boiling point (370 K)

R–O–H ···· O–H–R ← intermolecular H-bond in propanol

Conclusion: Even though propanol has lower molecular mass, H-

bonding gives it a much higher boiling point than butane.

E5 Alcohols are comparatively more soluble in water than

hydrocarbons of similar molecular mass. Explain.

ANSWER

Alcohols can form hydrogen bonds with water through their –OH group:

R–O–H ···· H–O–H (alcohol–water H-bond)

This strong interaction makes alcohols soluble in water ("like dissolves like" —
both have H-bonding). Hydrocarbons have no –OH group, cannot form H-
bonds with water, and are therefore insoluble.

Solubility decreases as the alkyl chain grows longer (more hydrophobic

character outweighs H-bonding ability). Small alcohols (CH₃OH, C₂H₅OH)
are completely miscible with water.

E6 What is hydroboration-oxidation? Illustrate with an example.

How does it differ from acid-catalysed hydration?

ANSWER

Hydroboration-oxidation is a two-step method to convert alkenes to

primary alcohols via anti-Markovnikov addition.
 Step 1 — Hydroboration: 3 CH₃–CH=CH₂ + (BH₃)₂/THF → (CH₃–
CH₂–CH₂)₃B [Boron adds to less substituted carbon] Step 2 —
Oxidation: (CH₃CH₂CH₂)₃B + H₂O₂/NaOH → 3 CH₃–CH₂–CH₂–OH
[Propan-1-ol — a primary alcohol]

HYDROBORATION- ACID HYDRATION (H

H⁺ /
FEATURE
OXIDATION H₂O)

Rule followed Anti-Markovnikov Markovnikov

Product from Propan-1-ol (1°) Propan-2-ol (2°)

propene

Mechanism Concerted, no Via carbocation

carbocation

Rearrangement? No Possible

E7 How will you synthesise the following?

(i) 1-Phenylethanol from a suitable alkene
(ii) Cyclohexylmethanol from alkyl halide via SN2
(iii) Pentan-1-ol from a suitable alkyl halide

ANSWER

(i) Styrene (C₆H₅–CH=CH₂) + H₂O/H⁺ → C₆H₅–CH(OH)–CH₃

[Markovnikov addition → 1-Phenylethanol, a 2° benzylic
alcohol]

(ii) Chloromethylcyclohexane (C₆H₁₁–CH₂Cl) + NaOH(aq) →

C₆H₁₁–CH₂OH + NaCl [SN2 at primary carbon →
Cyclohexylmethanol]

(iii) 1-Bromopentane (CH₃(CH₂)₃CH₂Br) + NaOH(aq) →

 CH₃(CH₂)₃CH₂OH + NaBr [SN2 → Pentan-1-ol]

E8 Name the reagents used in the following reactions (alcohol-

related):
(i) Oxidation of primary alcohol to carboxylic acid
(ii) Oxidation of primary alcohol to aldehyde
(iii) Benzyl alcohol to benzoic acid
(iv) Dehydration of propan-2-ol to propene
(v) Butan-2-one to butan-2-ol

ANSWER

REACTION REAGENT

(i) 1° alcohol Carboxylic acid Acidified K₂Cr₂O₇ or KMnO₄/H⁺

(ii) 1° alcohol Aldehyde (no PCC (Pyridinium Chlorochromate)

overoxidation)

(iii) Benzyl alcohol Benzoic acid Alkaline KMnO₄

(iv) Propan-2-ol Propene Conc. H₂SO₄ at 443 K (or 60% H₂SO₄

(dehydration) at 373 K)

(v) Butan-2-one Butan-2-ol LiAlH₄ or NaBH₄

(reduction)

E9 Give reason for higher boiling point of ethanol compared to

methoxymethane (dimethyl ether), both having the same
molecular formula C₂H₆O.

ANSWER

Both have the same molecular formula C₂H₆O but very different boiling
points:

BOILING
COMPOUND INTERMOLECULAR FORCES
POINT

Ethanol (CH₃CH₂OH) 351 K (78°C) Strong H-bonding (O–

H···O)

Dimethyl ether (CH₃–O– 248 K (– Only van der Waals

CH₃) 24°C) forces

Ethanol has an O–H group capable of forming strong intermolecular

hydrogen bonds. Dimethyl ether has no O–H; oxygen is flanked by two alkyl
groups and can only act as H-bond acceptor weakly, relying mostly on van
der Waals forces. Hence ethanol has a significantly higher boiling point.

E10 How are the following conversions carried out?

(i) Propene Propan-2-ol
(ii) Benzyl chloride Benzyl alcohol
(iii) Ethyl magnesium chloride Propan-1-ol
(iv) Methyl magnesium bromide 2-Methylpropan-2-ol

ANSWER

(i) CH₃–CH=CH₂ + H₂O/H⁺ → CH₃–CH(OH)–CH₃ [Acid-catalysed

hydration, Markovnikov → propan-2-ol]

(ii) C₆H₅–CH₂Cl + NaOH(aq) → C₆H₅–CH₂OH + NaCl [SN2

hydrolysis → Benzyl alcohol]

(iii) C₂H₅–MgCl + HCHO (methanal) →(i) dry ether (ii) H₃O⁺→

CH₃CH₂CH₂OH [Propan-1-ol, 1° alcohol] Grignard +
formaldehyde → always primary alcohol
 (iv) CH₃–MgBr + (CH₃)₂C=O (acetone) →(i) dry ether (ii)
H₃O⁺→ (CH₃)₃C–OH [2-Methylpropan-2-ol, tertiary alcohol]
Grignard + ketone → 3° alcohol

E11 When 3-methylbutan-2-ol is treated with HBr, the major

product is 2-bromo-2-methylbutane (not 2-bromo-3-
methylbutane). Explain via mechanism.

ANSWER

3-Methylbutan-2-ol: CH₃–CH(OH)–CH(CH₃)₂

Step 1 — Protonation of OH: CH₃–CH(OH)–CH(CH₃)₂ + H⁺ → CH₃–

CH⁺–CH(CH₃)₂ + H₂O [Forms 2° carbocation at C-2] Step 2 —
Hydride shift (rearrangement): CH₃–CH⁺–CH(CH₃)₂ → CH₃–CH₂–
C⁺(CH₃)₂ [2° carbocation rearranges to 3° carbocation via
hydride shift from C-3 to C-2] Step 3 — Attack of Br⁻ on 3°
carbocation: CH₃–CH₂–C⁺(CH₃)₂ + Br⁻ → CH₃–CH₂–CBr(CH₃)₂ [2-
Bromo-2-methylbutane — major product]

Key concept: Carbocation rearrangement (hydride shift) occurs when

a more stable carbocation (3°) can be formed from a less stable one
(2°). Always follow the stability order: 3° > 2° > 1°.

NCERT Ch. 11 · Alcohols · Class 12 Chemistry 18 Questions Total