RM

NEET & AIIMS 2018-19

M-CAPS-36 : CHEMISTRY
(Medical-Classroom Assessment Practice Sheet)
Topics covered : Common and IUPAC names of alcohols and ethers, Preparation of aliphatic alcohols and Aromatic
alcohols. Physical properties and Chemical reactions, of alcohols and Phenols.

Choose the correct answers :

1. Which of the following is an allylic alcohol? 6. The products formed in the reaction are
(1) CH2 CH — CH2 —OH
CH3 — CH = CH2 ⎯⎯⎯⎯⎯⎯
(i) B2H6
– →
(ii) H2O2 ,OH
OH
OH
(2) |
(1) CH 3 — CH—CH3 and B(OH)3

CH3 (2) CH 3 — CH 2—CH 2—OH and B(OH)3

|
(3) CH3 — C CH — OH OH
|
(4) Both (1) & (2) (3) CH 3 — CH—CH3 and BH3
2. Choose the secondary alcohol among the following
(4) CH3 — CH2 —CHO and B(OH)3
(1) Isobutyl alcohol (2) Isopropyl alcohol
7. Identify the products obtained in the following
(3) Isopentyl alcohol (4) Neopentyl alcohol
reaction
3. The alcohol having least solubility in water is
O
(1) Ethanol (2) 1-Propanol
(3) 1-Butanol (4) 1-Pentanol O H2 / Pd
Products
4. The correct structure of hydroquinone or quinol is O

O OH
O
(1) HO — CH2 — CH2 — OH and
(1) (2)
HO — CH2— CH2 — CH2 — OH
O OH (2) 2 moles of HO — CH2 — CH2 — OH
OH O
OH
(3) (4)
OH O
(3)
5. In acid catalysed hydration of alkenes, reaction O
intermediate formed is
OH
(1) Free radical (2) Carbocation
(3) Carbanion (4) Carbene (4) 2 moles of HO — CH2— CH2 — CH2 — OH

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M-CAPS : 36 (Medical-Classroom Assessment Practice Sheet) Regular Medical 2018-19

8. Which of the following product is expected to form 13. Products A, B and C in the following reactions are
in the given reaction? Hg(OAc)2THF.H2O +
H2 O/H
C – CH3—CH—CH CH2 A
NaBH4/OH |
CH3CHO ⎯⎯⎯⎯⎯
(i)CH3MgBr
(ii)H2O
→ CH3
(i) BH3.THF
(1) CH3—CH2—OH (ii) H2O/OH

(2) CH — CH—OH B
3
| OH
CH3
(1) A : CH3 — CH — CH — CH3
(3) CH3—CH2—CH2—OH
CH3
(4) Both (2) & (3) B : CH3 — CH — CH2— CH2 — OH
9. Phenol is also known as CH3
(1) Phenolic acid OH

(2) Hydroxy cinnamic acid C = CH3 — CH — CH— CH3

(3) Carbolic acid CH3
(4) Hydroxy carbolic acid OH

10. The product, P formed in the reaction is (2) A : CH3 — C — CH2 — CH3

CH3
(i) Oleum
+ P B : CH3 — CH — CH2— CH2 — OH
(ii) NaOH (iii) H
CH3
SO3H SO3H OH
OH C : CH3 — CH — CH — CH3
(1) (2)
CH3
OH
SO3H OH
(3) A : CH3 — CH — CH — CH3

(3) (4) CH3

B : CH3 — CH — CH2— CH2 — OH

OH CH3
11. Correct order of boiling point is OH

(1) n-butane < ethoxyethane < pentan-1-ol C : CH3 — C — CH2 — CH3

(2) n-butane < pentan-1-ol < ethoxyethane CH3
(3) Ethoxyethane < n-butane < pentan-1-ol OH
(4) Pentan-1-ol < ethoxyethane < n-butane (4) A : CH3 — C — CH2 — CH3
12. When cumene is oxidised in the presence of air
CH3
followed by treatment with dilute acid, the products
obtained are OH

(1) Benzoic acid and Methanol B : CH3 — CH — CH — CH3

(2) Phenol and Acetone CH3
(3) Benzoic acid and Acetone C : CH3 — CH — CH2— CH2 — OH
(4) Phenol and Acetaldehyde CH3

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Regular Medical 2018-19 M-CAPS : 36 (Medical-Classroom Assessment Practice Sheet)

18. Arrange the following in order of increasing basic

BH3. THF
P strength.
14. H2O2, OH—

CH3 CH3
NaOH, C2H5ONa, CHONa
Major product P in the above reaction is CH3
(I) (II) (III)
(1) (2) (1) (III) < (II) < (I)
CH3 CH3 OH
(2) (II) < (III) < (I)
OH H H (3) (I) < (II) < (III)
OH
(3) (4) (4) (II) < (I) < (III)
CH3 H H
OH 19. The correct decreasing order of acidic character of
following phenols is
H OH CH3
O O OH OH OH
CH2 — C — OCH3 NO2
15.
A
B NO2
OH O NO2
OH
CH2 — C — OCH3 (I) (II) (III)

(1) (I) > (II) > (III)

The reagents, A and B are respectively (2) (I) > (III) > (II)
(1) H2/Pt, NaBH4 (2) H2O/H+, NaBH4 (3) (III) > (I) > (II)
(3) NaBH4, LiAlH4 (4) LiAlH4,NaBH4 (4) (II) > (III) > (I)
16. Which of the following statement is correct for
20. Acetylation of salicylic acid produces
alcohols?
(1) They react only as a nucleophile (1) Adipic acid
(2) They react only as an electrophile (2) Picric acid
(3) They react both as a nucleophile and an (3) Glutaric acid
electrophile
(4) Aspirin
(4) They neither react as a nucleophile nor an
electrophile 21. Product formed in the following reaction is
17. The reaction in which hydrogen is not one of the CH3
product is | Cu
(1) CH3 – CH2 – OH + Na ⎯→ CH3 — C — OH 573 K
|
CH3 CH3

(2) CH3 — C — OH + Al ⎯→ O
CH3 (1) CH3 — C — CH 3
OH
CH3
(3) + Na ⎯→ |
(2) CH 3 — C CH2

OH (3) CH3—CH2— COOH

CH3
(4) + NaOH ⎯→ |
(4) CH 3 — CH — CHO

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M-CAPS : 36 (Medical-Classroom Assessment Practice Sheet) Regular Medical 2018-19

22. Consider the following reaction and identify the 23. Formation of Salicylic acid from phenol (Kolbe's
products reaction) is an example of
(1) Electrophilic addition reaction
OH
(2) Nucleophilic addition reaction
Conc. HNO3 dil. HNO3
B A (3) Electrophilic substitution reaction
low temp.
(4) Nucleophilic substitution reaction
24. Reaction intermediate formed in the formation of
OH OH salicylaldehyde from phenol (Reimer-Tiemann
reaction) is
(1) A : and B : (1) Carbocation (2) Free radical
NO2 (3) Carbanion (4) Carbene
NO2 25. The structure of the product formed on oxidation of
phenol with chromic acid is
OH OH COOH OH
NO2 COOH
(2) A : + and (1) (2)

NO2 O O
OH
(3) (4)
NO2 NO2
B:
O
26. Major product P formed in the reaction is
NO2
H SO
CH3 − CH2 − OH ⎯⎯⎯⎯
2 4
→ P
OH 413 K

NO2 NO2 (1) CH 2 CH2

(3) A : and CH2 CH2

(2)
NO2 O

OH (3) CH3 − CH2 − O − CH2 − CH3

OH
(4) CH3 − O − CH3
B: NO2 +
27. Which of the following molecules has zero dipole
moment?
NO2
OH Cl
NO2
(1) (2)
(4) A : and
OH Cl
OCH3
NO2

(3) CH3 − O − CH3 (4)

B:
O2N NO2 OCH3

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Regular Medical 2018-19 M-CAPS : 36 (Medical-Classroom Assessment Practice Sheet)

28. Product B in the following reaction is O OH

H2SO4 H2O/H2SO4
CH2 —OH A B (3) A : B:
Δ

OH
OH O OH
(1) (2)
(4) A : B:
OH
OH CH3 30. The final product D formed in the following series
(3) CH3 (4)
of reactions is
OH
29. Identify A and B in the following sequence of
CrO3 (i) CH3MgBr
reaction A B
H2SO4 (ii) H2O
O Δ H2SO4

H+ LiAlH4 (i) BH3,THF

A B D C
Heat (ii) H2O2, OH
OH CH3 CH3
O OH
OH OH

(1) A : B: (1) (2)

O CH3 CH3
OH
OH OH
(2) A : B:
(3) (4)

  

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 RM

NEET & AIIMS 2018-19

M-CAPS-36 : CHEMISTRY
(Medical-Classroom Assessment Practice Sheet)

ANSWERS
1. (4) (E) 2. (2) (E) 3. (4) (E) 4. (2) (M) 5. (2) (E)
6. (2) (M) 7. (2) (M) 8. (2) (E) 9. (3) (E) 10. (4) (M)
11. (1) (M) 12. (2) (M) 13. (2) (VD) 14. (3) (D) 15. (4) (D)
16. (3) (E) 17. (4) (E) 18. (3) (M) 19. (3) (M) 20. (4) (M)
21. (2) (E) 22. (2) (M) 23. (3) (E) 24. (4) (E) 25. (3) (M)
26. (3) (M) 27. (2) (E) 28. (2) (D) 29. (3) (D) 30. (2) (VD)

Question Level Questions Number

Easy (E) – 12 1, 2, 3, 5, 8, 9, 16, 17, 21, 23,
24, 27
Medium (M) – 12 4, 6, 7, 10, 11, 12, 18, 19, 20, 22,
25, 26
Difficult (D) – 04 14, 15, 28, 29

Very Difficult (VD) – 02 13, 30

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