1

Ummeed NEET 2025

Workbook Alcohols, Phenols & Ethers By Pankaj Sir (Popu Mama)
General Introduction: B. Allylic alcohols:

C. Benzylic alcohols:

Classification of Alcohols:
(ii) Compounds containing Csp2-OH bond:
Mono, Di, Tri or Polyhydric alcohols:
A. Vinylic alcohols:

C.Q. 1. Classify the following as primary, secondary and

tertiary alcohols: [NCERT Exemplar]

(i) Compounds containing Csp3-OH bond:

A. Primary, Secondary & Tertiary alcohols:

Solution.
 3

Solution.

B. By Hydroboration-Oxidation (HBO):

C.Q. 5. Assertion: Addition reaction of water to but-1-ene in

acidic medium yields butan-1-ol.
Reason: Addition of water in acidic medium proceeds
through the formation of primary carbocation.
[NCERT Exemplar]
(1) Assertion and reason both are correct and reason
is correct explanation of assertion.
(2) Assertion and reason both are wrong statements.
(3) Assertion is correct statement but reason is
wrong statement.
(4) Assertion is wrong statement but reason is
correct statement.
Solution.

C.Q. 6. Identify end products A, B and C of the following

reactions:
(i) D+
CH3CH = CH 2 ⎯⎯⎯⎯
→ A;CH3CH = CH 2
(ii) H 2O

(i)H + (i)D+
⎯⎯⎯⎯
→ B;CH3CH = CH 2 ⎯⎯⎯⎯
→C
(ii)D2O (ii)D2O

(1) CH3 C HCH3 in all cases

|
OH
(2) CH3CH(OH)CH2D, CH3CH(OD)CH3,
CH3CH(OD)CH2D
(3) CH3 C HCH3 in all cases
|
OD
(4) CH3 C HCH 2 D
| in all cases
OD
 5

Solution. C.Q. 11. The final product A, formed in the following

reaction sequence is: [JEE Mains 2024]

(1)
(2)
C.Q. 10. Propan-1-ol can be prepared from propene by:
[AIIMS 2003]
(3)
(1) H2O/H2SO4
(2) Hg(OAc)2/H2O followed by NaBH4
(3) B2H6 followed by H2O2 (4)
(4) CH3CO2H/H2SO4
Solution. Solution.

2. By Grignard Reagent:
C.Q. 12. What is the IUPAC name of the organic compound
formed in the following chemical reaction?
[NEET 2021]

(1) Pentan-2-ol (2) Pentan-3-ol

(3) 2-methyl butan-2-ol (4) 2-methyl propan-2-ol
Solution.

C.Q. 13. Which of the following are the starting materials for
the Grignard's synthesis of tert. butyl alcohol?
(1) CH3MgI + CH3COCH3

(2) CH3MgI + CH3CHOHCH3

(3) CH3CH2MgBr + CH3COCH3

(4) CH3CH2MgBr + CH3CHO

Solution.
 7

Solution. Solution.

2. From Benzene Sulphonic Acid:

C.Q. 16.

Product A is:

(1) (2)

C.Q. 18. When sodium benzene sulphonate is fused with

(3) (4) sodium hydroxide (solid), the product formed is:
(1) benzene
Solution. (2) phenol
(3) benzene triphenol
(4) none of these
Solution.

Methods of Preparation of Phenols:

1. Dows Process:

3. From Diazonium salt:

C.Q. 17.

The above reaction requires which of the following

reaction conditions? [JEE Mains 2021]
(1) 573 K, Cu, 300 atm
(2) 623 K, Cu, 300 atm
(3) 573 K, 300 atm
(4) 623 K, 300 atm
 9

Chemical Properties of Alcohols:

1. Acidic Nature of alcohol:
C.Q. 24.
Major product of above esterification reaction is:

(1)

(2)
C.Q. 23. ClCH2CH2OH is stronger acid than CH3CH2OH
because of: [AIIMS 2016]
(1) –I effect of Cl increases negative charge on O
atom of alcohol. (3)
(2) –I effect of Cl disperses negative charge on O atom
to produce more stable cation.
(3) –I effect of Cl disperses negative charge on O atom
to produce more stable anion.
(4)
(4) None of these
Solution.
Solution.

2. Esterification:

3. Reaction with PX3:

 11

6. Reaction with HX: 7. Dehydration:

C.Q. 29. What is the correct order of reactivity of alcohols in

the following reaction? [NCERT Exemplar]
ZnCl2
R—OH + HCl → R—Cl + H2O
(1) 1° > 2° > 3° (2) 1° < 2° > 3°
(3) 3° > 2° > 1° (4) 3° > 1° > 2°
Solution.

C.Q. 30. Given below are two statements: [NEET 2022]

Statement-I: In Lucas test, primary, secondary and
tertiary alcohols are distinguished on the basis of their
reactivity with conc. HCl + anhy. ZnCl2, known as
Lucas Reagent.
Statement-II: Primary alcohols are most reactive and OP Points:
immediately produce turbidity at room temperature on • Formation of Carbocations.
reaction with Lucas Reagent.
• Rearrange If Possible.
(1) Statement I is incorrect but Statement II is
correct. • R.O.R. or Reactivity α Stability of 1st Carbocation
(2) Both Statement I and Statement II are correct. • R.O.R. r = k[R-+OH2]1
(3) Both Statement I and Statement II are incorrect.
(4) Statement I is correct but Statement II is • E1 mechanism
incorrect. • More stable alkene is the major product.
Solution. C.Q. 31. Find out the major product for the following reaction.

[JEE Mains 2023]

 13

Chemical Properties of Phenols: Solution.

1. Acidic Nature of Phenol:

A. Reaction with metals:

C.Q. 36. Phenol is less acidic than ______________.

[NCERT Exemplar]
(1) ethanol (2) o-nitrophenol B. Reaction with NaOH:
(3) o-methylphenol (4) o-methoxyphenol
Solution.

C.Q. 37. Mark the correct order of decreasing acidic strength

of the following compounds. [NCERT Exemplar]
C. Reaction with NaNH2:

D. Reaction with NaHCO3:

(1) e > d > b > a > c

(2) b > d > a > c > e
(3) d > e > c > b > a
(4) e > d > c > b > a
 15

(ii) With Conc. nitric acid: C.Q. 40. Assertion: Phenols give o-and p-nitrophenol on
nitration with conc. HNO3 and H2SO4 mixture.
Reason: -OH group in phenol is o-, p- directing.
[NCERT Exemplar]
(1) Assertion and reason both are correct and reason
is correct explanation of assertion.
(2) Assertion and reason both are wrong statements.
(3) Assertion is correct statement but reason is
wrong statement.
(4) Assertion is wrong statement but reason is
correct statement.
Solution.

B. Halogenation:
C.Q. 39. Identify compound (Z) in the following reaction (i) Mono bromination:
sequence. [JEE Mains 2024]

(1) (2)

OP Points:
• The usual halogenation of benzene takes place in the
(3) (4)
presence of a Lewis acid, such as FeBr3 which
polarises the halogen molecule.
Solution. • In case of phenol, the polarization of bromine
molecule takes place even in the absence of Lewis
acid.
• It is due to the highly activating effect of –OH group
attached to the benzene ring.
 17

C.Q. 44. In the reaction [AIIMS 2017]

CO2 + HCl
Phenol ⎯⎯⎯
→ (A) ⎯⎯⎯⎯
NaOH
→(B).Here B is:
140 C

(1) benzaldehyde
(2) chlorobenzene
(3) benzoic acid
(4) salicylic acid
Solution. 1. On treating phenol with chloroform in the presence
of sodium hydroxide, –CHO group is introduced at
ortho position of benzene ring.
2. This reaction is known as Reimer-Tiemann reaction.
3. The intermediate substituted benzal chloride is
hydrolyzed in the presence of alkali to produce
C.Q. 45. Assertion: Phenol undergoes Kolbe reaction, salicylaldehyde.
ethanol does not.
Reason: Phenoxide ion is more basic than ethoxide C.Q. 46. In Reimer-Tiemann reaction, phenol is converted
ion. [AIIMS 2015] into salicylaldehyde through an intermediate. The
(1) If both Assertion and Reason are correct and the structure of intermediate is ______.
Reason is the correct explanation of Assertion. [JEE Mains 2024]
(2) If both Assertion and Reason are correct but
Reason is not the correct explanation of
Assertion. (1) (2)
(3) If Assertion is correct but Reason is incorrect.
(4) If both the Assertion and Reason are incorrect.
Solution.
(3) (4)

Solution.

5. Reimer-Tiemann Reaction:

C.Q. 47. Phenol treated with chloroform in presence of

sodium hydroxide, which further hydrolysed in
presence of an acid results [JEE Mains 2024]
(1) Salicylic acid
(2) Benzene-1, 2-diol
(3) Benzene-1, 3-diol
(4) 2-Hydroxybenzaldehyde
Solution.
 19

2. Bromine water test: Methods of Preparation of Ethers:

1. By Dehydration of Alcohols:

C.Q. 50.

The given reaction can occur in the presence of:

(A) Bromine water (B) Br2 in CS2, 273 K
(C) Br2/FeBr3 (D) Br2 in CHCl3, 273 K
Choose the correct answer from the option given C.Q. 52. What will be the reactant and reaction condition
below: [JEE Mains 2021] required for the given reaction?
(1) (A) and (C) only (2) (B), (C) and (D) only CH3CH2OH + ? → C2H5OC2H5
(3) (B) and (D) only (4) (A), (B) and (D) only (1) H2SO4, 413 K (2) H2SO4, 443 K
Solution. (3) HNO3, 413 K (4) HNO3, 443 K
Solution.

C.Q. 51. Phenol can be distinguished from ethanol by the C.Q. 53. Excess of ethanol when heated with conc. H2SO4
reactions with _________. [NCERT Exemplar] at 140°C, the compound obtained is:
(1) Br2/water (1) ethene
(2) Na (2) diethyl sulphate
(3) Neutral FeCl3 (3) ethoxy ethane
(4) Both (1) & (3) (4) ethyl hydrogen sulphate
Solution. Solution.
 21

Chemical Properties of Ethers: C.Q. 59. Major product formed in the following reaction is
1. Cleavage of C-O bond: A. Reaction with HX a mixture of: [JEE Mains 2024]

(1)

(2)

(3)

(4)

Solution.

C.Q. 58. Which one of the following, with HBr will give a
phenol? [JEE Mains 2025] C.Q. 60. Consider the following reaction

(1)

Identify products A and B. [NEET 2023]

(2)
(1)

(3) (2)

(3)
(4)

(4)
Solution.
Solution.
 23

C.Q. 62. Which one of the following reactions is NOT B. Nitration:

possible? [JEE Mains 2024]

(1)

(2)

(3)

(4)

Solution.
C.Q. 64. The major products formed:

A and B respectively are: [JEE Mains 2024]

C.Q. 63. The major product obtained on the
monobromination (with Br2/FeBr3) of the following
(1)
compound A is: [AIIMS 2006]

(2)

(2)
(1)

(3)

(3) (4)

Solution.

(4)
 25

2. Melting Point (1) (A), (B) and (C) Only

(2) (B) and (D) Only
(3) (A) and (B) Only
(4) (A) and (C) Only
Solution.

3. Solubility

C.Q. 69. Arrange the following compounds in increasing

order of boiling point. [NCERT Exemplar]
C.Q. 67. Given below are two statements: Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
Statement-(I): The boiling points of alcohols and (1) Propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol
phenols increase with increase in the number of C-
(2) Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
atoms.
(3) Pentan-1-ol, butan-2-ol, butan-1-ol, propan-1-ol
Statement-(II): The boiling points of alcohols and
phenols are higher in comparison to other class of (4) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-1-ol
compounds such as ethers, haloalkanes. Solution.
In the light of the above statements, choose the
correct answer from the options given below:
[JEE Mains 2025]
(1) Statement I is true but Statement II is false.
(2) Both Statement I and Statement II are true.
C.Q. 70. Assertion: Boiling points of alcohols and ethers are
(3) Both Statement I and Statement II are false.
high.
(4) Statement I is false but Statement II is true.
Reason: They can form intermolecular hydrogen-
Solution.
bonding. [NCERT Exemplar]
(1) Assertion and reason both are correct and reason
is correct explanation of assertion.
(2) Both assertion and reason are correct statements
but reason is not correct explanation of
C.Q. 68. The steam volatile compounds among the assertion.
following are: (3) Assertion and reason both are wrong statements.
(4) Assertion is wrong statement but reason is
correct statement.
(A) (B) Solution.

(C) (D)
Choose the correct answer from the options given
below: [JEE Mains 2025]

“अवसर की प्रतीक्षा में मत बैठो । आज का अवसर ही सवोत्तम है”

 2

CrO
24. R − CH − R ' ⎯⎯⎯
3
→
|
OH 33. ⎯⎯⎯⎯
→

CH3
|
Cu
25. CH3 − C − OH ⎯⎯⎯→
573K
| Zn
CH3 34. ⎯⎯→

CH COOCOCH
26. PhOH ⎯⎯⎯⎯⎯⎯⎯
3 3
→ +
Na Cr O
35. ⎯⎯⎯⎯⎯
2 2 7
→
H 2SO4

dil.HNO
27. ⎯⎯⎯⎯→
3
ZnO−Cr O
36. CO + 2H 2 ⎯⎯⎯⎯⎯
2 3
→
250atm
600 K

H SO
Conc.HNO3
37. CH3CH 2OH ⎯⎯⎯⎯
2 4→
413K
28. ⎯⎯⎯⎯⎯→

38. CH3ONa + CH3 − Cl →

29. ⎯⎯⎯⎯
→ 39. (CH3 )3 CONa + CH3Cl →

40. (CH3 )3 C − Cl + CH3ONa →

HBr
41. CH3OC2 H5 ⎯⎯⎯
→ +
30. ⎯⎯⎯⎯
→
HI
42. CH3 − O − C(CH3 )3 ⎯⎯→ +

Br
H SO 43. ⎯⎯⎯
2→
31. ⎯⎯⎯⎯
2 4→

44. ⎯⎯⎯⎯
→
32. ⎯⎯⎯⎯
→
 4

Hint and Solutions

1. R − CH − CH3 CH3
| | 36. CH3OH
OH 25. CH3 − C = CH 2
14.
37. C2H5OC2H5
2. R – CH2 – CH2OH 26. CH3COOPh, 38. CH3OCH3
15. RONa CH3COOH
39. (CH3)3COCH3
3. 16. CH3COOCH3 +
H2O18
27. 40.
4. RCH2OH

5. RCH2OH 17. 41. CH3Br + C2H5OH

28.
6. RCOOH 42. CH3OH + C(CH)3I
18. R–X
7. R − CH − OH
| 29. Br2 + CS2
R' 43.
19. 30. Br2 + H2O
8. RCOR

9. NaOH, 623K/300
44. CH3COCl/Anhyd.
atm 20.
31. AlCl3

21. CH2 = CH2 45. Conc. H2SO4 / Conc.

HNO3
10.
22. R − C −R 32. CHCl3 + aq. NaOH
|| 46. PhOH + CH3I
11. NaNO2/HCl, H2O CH2
33. CO2, NaOH/H+
warm 47. Warm H2O

34. 48. CH3COOPh

23.
12. 49. R – CH2 – I

24. R − C− R '
|| 50. PhOCH3
13. R – O – Na 35.
O
 NEET

Q7 In the given reaction, Q10 In the given reaction, the product ‘A’ is;
PCC

CH3–CH=CH–CH2–OH −
−→ Product

Product is;
(A) CH3–CH2–CH2–CH2–OH
(B) CH3–CH2–CH2–CH3
(C) CH3–CH=CH–CHO
(D) CH3–CH=CH–COOH (A)

Q8 Given below are two statements: one is labelled

as Assertion (A) and the other is labelled as
Reason (R).
Assertion A: The ortho and para nitrophenols
cannot be separated by steam distillation.
(B)
Reason R: o-Nitrophenol is steam volatile due to
intramolecular hydrogen bonding while p-
nitrophenol is less volatile due to intermolecular
hydrogen bonding which causes the association
of molecules.
In the light of the above statements, choose the
correct answer from the options given below: (C)
(A) A is true but R is false.
(B) A is false but R is true.
(C) Both A and R are true and R is the correct
explanation of A.
(D) Both A and R are true but R is NOT the
correct explanation of A.
(D)
Q9 Identify 1° alcohol in the following given alcohols;

Q11 When phenol is treated with excess bromine

water, it gives?
(A) m-Bromophenol
(B) o-and m-Bromophenol
(C) 2,4-Dibromophenol
(D) 2,4,6-Tribromophenol

Q12 Given below are two statements: one is labelled

(A) 1 and 2 only
as Assertion (A) and the other is labelled as
(B) 2 and 3 only
Reason (R)
(C) 1 only
Assertion (A): Phenols react with active metals
(D) 1, 2 and 3
such as sodium, potassium and aluminium to
yield phenoxides and hydrogen.

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 NEET

(C) ZnO + benzene Q25 Which of the following will not be oxidised by
(D) Benzoic acid PCC?
(A)
Q19 Which of the following is not true in case of
reaction with heated copper at 300°C?
(A) Tertiary alcohol → Ketone
(B) Secondary alcohol → Ketone
(C) Primary alcohol → Aldehyde
(B)
(D) Tertiary alcohol → Alkene

Q20 In Reimer-Tiemann reaction reagent used are:

(A) CHCl3 and aq. NaOH
(B) CH3Cl and aq. NaOH
(C)
(C) CH3Cl and POCl3
(D) CH3Br and alc. NaOH
(D)
Q21 Which of the following product is formed on acid
catalysed hydration of 2-Phenylpropene?
(A) 1-Phenylpropan-2-ol
(B) 1-Phenylpropan-1-ol
(C) 1-Phenylpropan-3-ol
Q26 Isobutyl alcohol can be obtained by reaction of:
(D) 2-Phenylpropan-2-ol
(A) C2H5MgBr and CH3CHO
Q22 C6H5OH + CHCl3 + NaOH → Salicylaldehyde. (B) CH3MgBr and CH3CH2CHO
The intermediate involved in the above reaction (C) (CH3)2CHMgBr and HCHO
is; (D) CH3MgBr and CH3COCH3
(A) ⊕
(B) :CCl2
C HCl 2 Q27 Which is incorrect order of dehydration of
(C) ⊝
(D) ⊕
alcohol?
C Cl3 C HO
(A)
Q23 Which of the following is most acidic?
(A) Phenol (B) CH3CH2OH
(C) Picric acid (D) p-Nitrophenol (B)

Q24 When ethyl alcohol (C2H5OH) reacts with thionyl

chloride, in the presence of pyridine, the product
obtained is; (C)
(A) CH3CH2Cl + HBr
(B) C2 H6 + HCl ↑ + SO 2 ↑

­
(C) CH3 CH2 Cl + H2 O ↑ +O 2 ↑
(D)
(D) CH3 CH2 Cl + HCl ↑ + SO 2 ↑

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 NEET

3. It is acidic in nature. (A) Acid catalysed hydration of alkenes

Among the above, true statement(s) is/are: (B) Free radical halogenation of alkanes
(A) only 3 (B) only 1 and 3 (C) Reduction of aldehydes
(C) only 1 (D) 1, 2 and 3 (D) Hydroboration-oxidation of alkenes

Q37 In the given reaction Q42 For the preparation of alkyl halides from alcohols
HI
which among the following can not be used;
CH3 –CH2 – CH2 –O– CH2 –CH3 → [X]
(A) PCl5
(B) SOCl2
&[Y]
(C) Anhy. ZnCl2 + HCl(Conc.)
[X] and [Y] respectively be; (D) NaCl
(A) CH3CH2CH2OH and CH3CH2I
Q43 Which of the following is a tertiary alcohol?
(B) CH3CH2CH2I and CH3CH2OH
(A) CH3CH2OH (B) CH3CH(OH)CH3
(C) CH3CH2CH2I and CH2=CH2
(C) (CH3)3COH (D) CH2=CHCH2OH
(D) CH3–CH=CH2 and CH2=CH2
Q44 On treating phenol with chloroform in the
Q38 Given below are two statement: one is labelled
presence of sodium hydroxide followed by
as Assertion A and the other is labelled as
hydrolysis, which group is introduced at ortho
Reason R:
position of benzene ring?
Assertion A: Phenol is more acidic than p-
(A) –COOH (B) –CHCl2
methoxyphenol.
(C) –CHO (D) –CH2Cl
Reason R: –OCH3 shows +I-effect.
In the light of the above statements, choose the Q45 Match List I with List II
correct answer from the options given below:
(A) A is true but R is false. List I List II

(B) A is false but R is true.

(C) Both A and R are true and R is the correct
A. –CH2–OH I. Tertiary alcohol
explanation of A.
(D) Both A and R are true but R is NOT the
correct explanation of A. Secondary
B. II.
alcohol
Q39 An ether is more volatile than an alcohol having
the same molecular formula. This is due to;
(A) resonance in ethers C. III. Dihydric phenol
(B) alcohols having resonance structures
(C) inter-molecular hydrogen bonding in ethers
(D) inter-molecular hydrogen bonding in alcohols
D. IV. Primary alcohol
Q40 Which one of the following alcohols is least
soluble in water?
(A) CH3OH (B) C3H7OH Choose the correct answer from the options
(C) C4H9OH (D) C10H21OH given below:
(A) A-IV, B-II, C-I, D-III
Q41 Which of the following processes does not result
(B) A-III, B-II, C-IV, D-I
in the production of alcohol?
(C) A-II, B-I, C-III, D-IV

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 NEET

Answer Key
Q1 (A) Q26 (C)

Q2 (C) Q27 (B)

Q3 (B) Q28 (A)

Q4 (C) Q29 (D)

Q5 (C) Q30 (A)

Q6 (D) Q31 (A)

Q7 (C) Q32 (C)

Q8 (B) Q33 (B)

Q9 (C) Q34 (B)

Q10 (B) Q35 (C)

Q11 (D) Q36 (B)

Q12 (A) Q37 (A)

Q13 (D) Q38 (A)

Q14 (C) Q39 (D)

Q15 (C) Q40 (D)

Q16 (C) Q41 (B)

Q17 (B) Q42 (D)

Q18 (C) Q43 (C)

Q19 (A) Q44 (C)

Q20 (A) Q45 (A)

Q21 (D) Q46 (B)

Q22 (B) Q47 (C)

Q23 (C) Q48 (C)

Q24 (D) Q49 (A)

Q25 (A) Q50 (C)

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