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LAKSHYA JEE 2023

Alcohol, Phenol and Ethers DPP-02

1. Which of the following compounds on reaction with 6. The reagent required to convert propene to 1-
excess of CH3MgBr will give a tertiary alcohol? propanol is
(1) B2H6 followed by H2O2/NaOH
(1) (2) conc. H2SO4 followed by hydrolysis with
C2 H5CO 2 CH3 boiling water
(2)
(3) HBr followed by hydrolysis with aqueous
(3) C6 H5CHO
KOH
(4) C2 H5COOH (4) Hg(OCOCH3)2 followed by reduction with
NaBH4
2. Oxymercuration-demercuration reaction of
1-methylcyclohexene gives 7. Reaction of with RMgX followed by
(1) trans-2-methyl cyclohexanol
acid hydrolysis will lead to produce
(2) cis-2-methylcyclohexanol
(1) RCHOHR (2) RCHOHCH3
(3) 1-methyl cyclohexanol
(3) R2CHCH2OH (4) RCH2CH2OH
(4) mixture of cis- and trans-2-methylcyclo-
hexanol
CH3MgBr( excess )
8. Ethyl ester → P.
3. The product of the following reaction is The product P will be
( i )BH /THF
3

→
( ii )H 2O2 ,OH
(1) (2)
(1) 2-pentanol
(2) pentane
(3) pentan-2-one
(4) 1-pentanol (3) (4)

4. The reaction of Grignard reagent with formaldehyde

followed by acidification gives 9. When one of the following compounds will react with
(1) An aldehyde Grignard reagent to yield a primary alcohol containing
(2) A ketone two more carbons?
(3) A carboxylic acid (1) CH3CHO (2)
(4) A primary alcohols
(3) HCHO (4) CH3COCH3
5. What is the major product of the following
reaction?
CH MgI
3 10.

→ H3O⊕
Et 2O 
→

(1) (2)

Sum of number of 1° alcoholic groups in product

(P) and (Q) is:
(3) (4)
(1) 1 (2) 2
(3) 3 (4) 4
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11. Predict the product when given compound reacts 14. Which one of the following will produce a primary
with LiAlH4: alcohol by reacting with CH3MgI:
(1) Acetone
(2) Methyl cyanide
(3) Ethylene oxide
(4) Ethyl acetate
(1)
B2 H 6 H 2O2 /OH −
15. A  → B  → Isobutyl alcohol, A is
(1) Isobutane
(2) 2-Methyl Propene
(2) (3) 𝛽𝛽-Butylene
(4) 𝛼𝛼-Butylene

(3) 16. The only alcohol that can be prepared by the

hydration of ethene is
(1) Ethyl alcohol
(2) Propyl alcohol
(3) Isobutyl alcohol
(4)
(4) Methyl alcohol

H 2O, Hg(OAC)2
17. CH3 − CH − = CH CH 2 
NaBH 4 →(A),
|
CH 3
12. product (A) is: (1) predominantly is
(1) CH 3 − CH − CH 2 − CH 2 − OH
|
CH 3
(2) CH 3 − CH − CH − CH 3
(1) (2) | |
CH 3 OH
OH
|
(3) CH 3 − C − CH 2 − CH 3
|
(3) (4) CH 3
(4) CH3–CH2–CH2–CH2–CH2–OH

CH 3 CH 3
13. Propene, CH3–CH=CH2 can be converted to 1- | |
propanol by oxidation. Which set of reagents among 18. CH 3 − C −= CH CH 2 
→ CH 3 − C − CH − CH 3
| | |
the following is ideal to effect the conversion:
CH 3 CH 3 OH
(1) Alkaline KMnO4
This change can be done by
(2) B2H6 and alkaline H2O2
(1) acid catalysed hydration
(3) O3/Zn dust
(2) oxymercuration-demercuration
(4) OsO4/ CH4, Cl2
(3) hydroboration-oxidation
(4) any method mentioned above
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(4) Oxymercuration demercuration, hydroboration

19.
oxidation and hydration
Identify the major product ‘P’ is
23.

A is
(1) (2)
(1) (2)

(3) (4)
(3) (4)

20. RCH = CH2 adds on water in the presence of dilute

sulphuric acid or phosphoric acid to form
(1) R—CH(OH)—CH3 24.
(2) R—CH2—CH2OH
(3) R—CHOH—CH2—CH2—CHOH—R Reagent ‘A’ is
R — CH— CH 2 (1) BH3/H2O2/ ΘOH
| | (2) H2O/HΘ
(4) OH OH (3) Hg(OCOCH3)2/NaBH4
(4) Cl2
21. The major product of the following reaction is
25. In the given reaction

(1)
[X] will be
(1) LiAlD4/D2O
(2) (2) NaBD4/H2O
(3) LiAlD4/HOH
(4) NaBH4/D2O

(3) 26. When CH2 = CH–COOH is reduced with LiAlH4,

the compound obtained will be
(4) (1) CH3–CH2–CH2OH
(2) CH3–CH2–CHO
(3) CH3–CH2–COOH
22. X, Y, Z reaction are
(4) CH2 = CH–CH2OH

27. The hydroboration of 2-methyl propene yields

(1) 1° alcohol (2) 2° alcohol
(3) 3° alcohol (4) None

28. LiAlH4 converts acetic acid into

(1) Acetaldehyde (2) Methane
(3) Ethyl alcohol (4) Methyl alcohol
(1) Simple hydration reaction
29. A tertiary alcohol is obtained when CH3MgI reacts
(2) Hydroboration oxidation, hydration and
with
oxymercuration demercuration
(1) CH3CHO
(3) Hydroboration oxidation, oxymercuration
(2) CH3CH2CHO
demercuration and hydration
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(3) CH 3 − CH − CHO
| (1) (2)
CH 3
(4) CH3COCH3 (3) (4)
30. To prepare 3-ethylpentan-3-ol, the reactants needed
are 35. How many moles of alkene are required with one
(1) CH3CH2MgBr + CH3COCH2CH3 mole of diboarane in the formation of alcohol from
(2) CH3MgBr + CH3CH2CH2COCH2CH3 hydroboration-oxidation
(3) CH3CH2MgBr + CH3CH2COCH2CH3 (1) 2 (2) 3
(4) CH3CH2CH2MgBr + CH3COCH2CH3 (3) 4 (4) 5

31. Choose the major product of the following reaction 36. When ketones are treated with Grignard reagent
followed by hydrolysis with dilute acid, the product
is
(1) Primary alcohol (2) Secondary alcohol
(3) Tertiary alcohol (4) Alkene

(1) (2) 37. Propene on hydroboration oxidation produces

(1) Propan-1-ol
(2) Propan-2-ol
(3) Propane-1, 3-diol
(4) Propane-1, 2-diol
(3) (4)
38. Consider the following reaction
(i) H SO
2 4→Z
PBr
3 → X  alc.KOH Y 
32. The following compound on mercuration- Ethanol  → (ii) H O, ∆
2
demercuration produces the major product The product Z is
(1) CH3CH2OCH2CH2
(2) CH3CH2O – SO3H
(3) CH3CH2OH
(4) CH2 = CH2
(1)

(2) 39.

(1) (2)
(3)
(3) Both (4) None

(4) LiAlH
4→
C6 H5CHO 
40.
33. Which set of reagents is used for the purpose of (1) benzene (2) benzyl alcohol
adding water to an alkene in a Markovnikov (3) phenol (4) none
addition without rearrangement?
(1) BH3, THF followed by H2O, NaOH 41. Identify the reagent used in the following
(2) H2O, H2SO4
(3) Br2, H2O conversion
(4) Hg (O2CCH3)2, followed by NaBH4, NaOH
34. What is the major product of the following
reaction?
(1) LiAlH4 (2) NaBH4
(3) both (4) none
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(4) Methyl bromide and aluminium bromide

42. Ketone on reduction with sodium borohydride gives
(1) primary alcohol (2) secondary alcohol 45. Which of the following alcohols will give the most
(3) tertiary alcohol (4) none stable carbocation during dehydration?
(1) 2-methyl-1-propanol
43. Reagent used for the following conversion is (2) 2-methyl-2-propanol
(3) 1-Butanol
(4) 2-Butanol

(1) LiAlH4 (2) NaBH4

(3) both (4) none

44. 1-Phenylethanol can be prepared by the reaction of

benzaldehyde with
(1) Methyl bromide
(2) Ethyl iodide and magnesium
(3) Methyl iodide and magnesium (Grignard
reagent’s)
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Answer Key
1. (2) 16. (1) 31. (2)
2. (3) 17. (2) 32. (1)
3. (4) 18. (2) 33. (4)
4. (4) 19. (3) 34. (2)
5. (4) 20. (1) 35. (2)
6. (1) 21. (3) 36. (3)
7. (4) 22. (3) 37. (1)
8. (1) 23. (3) 38. (3)
9. (2) 24. (1) 39. (2)
10. (4) 25. (1) 40. (2)
11. (3) 26. (3) 41. (1)
12. (4) 27. (1) 42. (2)
13. (2) 28. (3) 43. (3)
14. (3) 29. (4) 44. (3)
15. (2) 30. (3) 45. (2)

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