CPP - Alcohol Ether Phenol

NAME: _______________________ BATCH: _______________ DATE: ______________
CHAPTER PRACTICE PROBLEMS

Subject: Chemistry Topic: Alcohol, Ether, Phenol
1. Which is hydrolysed to alcohol to a maximum extent?

(a) CH3F (b) CH3Cl (c) CH3I (d) CH3Br
2. In the following reaction, product formed:

Me
OH −
H Br  →
SN 1
Et
(a) retains configuration (b) inverts configuration
(c) is a racemic mixture (d) is a meso compound
3. In the following reaction, product formed:

Et
OH −
H I  →
SN 2
C 6 H5
(a) retains configuration (b) inverts configuration
(c) is a racemic mixture (d) is a meso compound
4. Carbonyl compounds are reduced to alcohols by hydride reagents. This reduction

involves:
(a) addition of two hydrogens across a C = O bond
(b) reduction of carbonyl group to an alkoxide which is protonated to alcohol
(c) both of the above (d) none of the above
5. In the following reaction, B and C are respectively:

O
NaBH 4 O LiAlH 4
C ←  → B
CH 3OH
O
A
OH O
(a) I: II:
OH
OH OH
(b) II, I (c) I in both cases (d) II in both cases
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6. C4H8O(A) changes to 3o alcohol by reduction with LiAlH4. Thus, A is
O
(a) CH3CCH2CH3 (b) CH3CH2CH2CHO
(c) (CH3)2C–––CH2 (d) CH3CH–––CHCH3
O O
7. C2H4O(A) reacts with CH3MgBr followed by decomposition with H3O ⊕ to give 1o
alcohol. Thus, A is
(a) CH2 = CHOH (b) CH3CHO
(c) CH2–––CH2 (d) none of these
O
8. What is the end-product of the following?
⊕
Mg ether HCHO H 3O
F Br  → →  →
(a) HOH2C CH2OH
(b) F CH2OH
(c) Br CH2OH
(d)
9. Which has maximum pKa value?

(a) (b) OH
OH
(c) (d)
OH OH
10. Isotopic O of I goes with:

O O
CH3COH + CH3CH2OH 
→ CH3COCH2CH3 + H2O
II I III IV
(a) IV (b) III (c) both of these (d) none of these
11. Consider oxidation of following alcohols:
A
I: CH2 = CHCH2OH  → CH2 = CHCHO
II: (CH3)3COH 
→ CH3C = CH2
CH3
C
III: CH3CH2OH  → CH3CO2H
D
IV: CH3CH = CHCH3  → CH3CO2H
A, B, C and D are oxidizing agents which are respectively:
A B C D
(a) MnO2 Cu/ ∆ H2CrO4 KMnO4/ ∆
(b) Cu/ ∆ MnO2 H2CrO4 KMnO4/ ∆
(c) MnO2 Cu/ ∆ KMnO4/ ∆ H2CrO4
(d) MnO2 H2CrO4 Cu/ ∆ KMnO4
H3 C
LiAlH 4
12. CH2 → A. A is:
H3C O
(a) CH3CHCH2OH (b) CH3CH2CH2CH2OH
CH3
CH3
(c) CH3C––OH (d) no reaction
CH3
13. Rate of hydration of

CH3
CH = CH2 CH = CHCH3 C = CH2

(I) (II) (III)
will be in order:
(a) I < II < III (b) I < III < II (c) II < I < III (d) III < II < I
O
CH 3 MgBr ( excess )
14. O  +
→ X, X is:
H 3O
H3 C OH
(a) OH (b) HO
H3 C OH
H3 C
O OH O
(c) CH3 (d)
15. Consider following reactions:
I: ONa + CH3I 
→
II: Br + CH3ONa 
→
III: (CH3)3C – Cl + CH3ONa  → IV: (CH3)3C – ONa + CH3Cl  →

Which of the above methods cannot be used in the synthesis of ether?
(a) I, IV (b) I, III (c) II, IV (d) II, III
16. Which is the nucleophile in the following reaction?

CH3OH + CH2N2  → CH3OCH3 + N2
(a) CH3OCH3 (b) N2 (c) CH3OH (d) CH2N2
17. Alkene can be converted to oxirane by oxidation using:

(a) m-CPBA (b) trifluoroperoxyacetic acid
(c) oxygen/Ag (catalyst) (d) all of the above
18. HI cleaves ether (A) forming:

A: CH2 – O – CH3
(a) CH2OH, CH3I (b) CH2I, CH3OH
(c) CH2I, CH3I (d) CH2OH, CH3OH
19. Which is correct statement about following reaction?

H
γ
CH3OH + CH3C –– CH2 
→
α O β
⊕
H
(a) α -bond is cleaved when product formed is
CH3CH –– CH2OCH3
OH
(b) β -bond is cleaved when product formed is
CH3CH –– CH2OH
OCH3
(c) α -bond is cleaved when product formed is
CH3CH –– CH2OH
OCH3
(d) β -bond is cleaved when product formed is
CH3CH –– CH2OCH3
OH
20. Select correct statement for the following reaction:

CH3
α β γ
CH 3OH
CH3O– + CH2 –– C –– CH3  →
x y
O
(a) Nucleophile attacks α -carbon and x-bond is cleaved
(b) Nucleophile attacks β -carbon and y-bond is cleaved
(c) Nucleophile attacks α -carbon and y-bond is cleaved
(d) Nucleophile attacks β -carbon and x-bond is cleaved
21. In the following reaction, final product is:

14
NaOC2 H 5
ClCH2CH – CH2  →
O
14 14
(a) ClCH2CHCH2OC2H5 (b) ClCH2CHCH2ONa
OH OC2H5
14 14
(c) CH2 –– CHCH2OC2H5 (d) CH2 –– CHCH2OC2H5
O O
22. Syn addition of diols takes place by using:

(a) OsO4/H2O2 (b) KMnO4/OH– (c) both of these (d) none of these
23. Boiling point of n-butanol is

(a) equal to that of n-butane (b) greater than that of n-butane
(c) lower than that of n-butane (d) 38oC
24. Grignard reaction with the compound,

O
C
CO 2H is not possible, because

(a) this compound is hypothetical (b) it has large steric hinderance
(c) the carbonyl group is less active (d) it has an acidic hydrogen
25.
CH3
H 2 SO4
H3 C C CH3 → X. In the reaction, X is
∆
CH2OH
CH3 H3 C H
(a) CH2 C (b) C C
CH2CH3 CH3
H3C
CH3
(c) CH3 C CH3 (d) Water
CH2OH
26. Halogenation of alcohols using halogen acids always/mostly give rearranged products
because
(a) free radicals are generated (b) carbocations are generated
(c) carbanions are generated (d) concentrated acids are used
X
27. CH3CH2MgBr  → CH3CH3. Here in this reaction, X is
(a) CH2 = CH2 (b) CH2 CH2 (c) H2O (d) CO2
O
28. p-Nitro phenol is
(a) more acidic than m-Nitrophenol (b) more acidic than phenol
(c) more acidic than benzoic acid (d) only (i) and (ii)
29.
OH OH
Br2
CS2
Br . Here mono bromination is observed
because
(a) electrophilicity of Br is decreased (b) ionization of phenol is decreased
(c) either (a) or (b) (d) both (a) and (b)
30.
OH
CH3CH2CH2OH
X. Here X is
H2SO4
OH
OH (b)
(a)
CH2CH2CH3 CH2CH2CH3
OH
O-CH 2CH2CH3
(d) CH3
(c)
CH
CH3
31.
CH3
H3 C C Cl + NaOC2H5 
→
CH3
CH3 CH3
C
(a) CH2 CH2 (b)
CH2
CH3
(c) H3 C C O C 2 H5 (d) No reaction
CH3
32.
Cl
+ CH3CH2CH2ONa
O-CH 2CH2CH3 Cl
(a) (b)
CH2CH2CH3
CH2CH2CH3
(c)
(d) No reaction
33. CH2 

Hg(OAc)2 NaBH 4
→  → A, A is
H3C CH3OH
CH3
H3C
(a) H3C OH (b)
OH
CH3
H3C
(c) H3C OCH3 (d)
OCH3
34. Which of the following methods will form cyclopentyl ethyl ether?
(a) ONa + CH3CH2Br (b) Br + CH3CH2ONa
(c) OH + CH3CH2Cl (d) + H3O+ + CH3CH2Cl
35. CH3ONa
 → A, A can be
Cl Cl
(a) (b)
OH 3C OCH3 OH 3C Cl
(c) (d) no reaction

Cl OCH3
36. CH3
+
Ag
 
→ A, A (predominant) is:
CH3CH 2 ONa
Cl
CH3 CH2CH3
(a) (b)
OCH2CH3 OCH2CH3
CH2CH3
(c) CH2CH2OCH2CH3 (d)
OCH2CH3
37. 18
H3C OH OH
H3 PO4
 → A (mix), A is
H3C CH3
18
H3C O H3C O
CH3 CH3
(a) H3C + H2O (b) H3C + H2O18
(c) both correct (d) none is correct
38. Which one of the following compounds is most rapidly hydrolysed by SN1
mechanism?
(a) CH3CH = CHCl (b) CH2 = CHCH2Cl
(c) CH2Cl (d) (C6H5)3CCl
39.
+
H3 O
CH CHCH3  → A (major)
(a) CH2 CHCH3 (b) CHCH2 CH3

OH OH
(c) CHCHCH3 (d) CH2CH2CH2OH

OHOH
40. H2C CH CH CH2 CH2 OH 

MnO2
→ A. A is
OH
(a) H2C CH C CH2 CH2 OH (b) H2C CH CH CH2 CHO
O OH
O
(c) H2C CH C CH2 CHO (d) H2C CH C CH2 C OH

O O
41. CH2CH3 CH CH2

C
OH
B A
CHCH3 CH2CH2OH
OH
Schemes A, B, C are
I: acid catalysed hydration
II: HBO
III: oxymercuration-demercuration
(a) I in all cases (b) I, II, III (c) II, III, I (d) III, I, II
42.
MnO 2
OH  → A, A is
OH
(a) OH (b) O
O OH
(c) O (d) O
O OH
CH 3MgBr (excess)
43. (C2H5O)2CO  +
→ A. A (alcohol) can also be obtained by
H 3O
O
CH3 MgBr (2 mol) CH 3 MgBr (2 mol)
(a) CH3CH2CHO 
H O+
→ (b) H3C CO C2H5  H O+
→
3 3
O
CH 3MgBr (1 mol)
(c) H3C C CH3  +
→ (d) as in (b) and (c)
H 3O
+
H 3O
44. Ester A (C4H8O2) + CH3MgBr (2-parts)  → C4H10O (alcohol B). Alcohol B
reacts fastest with Lucas reagent. Hence A and B are
O
(a) H3C C O C2H5 , (CH3)3COH
O
(b) H C O C3H7 , (CH3)2CHOH
O
(c) H3C C O C2H5 , (CH3)2CHOH
O
(d) H C O C3H7 , (CH3)3COH
45. CH3
cold CrO3
→ A  → B, A and B are:
alkaline KMnO4 AcOH
CH3 CH3
(a) OH , OH
OH O
CH3 CH3
-
C O
(b) OH ,
OH O
CH3 CH3
(c) OH ,
OH OH
(d) No formation of A and B
46. CH3
conc. H SO
CH3C CHCH3 →
2 4
A (predominant), A is:
CH3 OH
(a) (CH3)3CCH = CH2 (b) (CH3)2C = C(CH3)2
(c) H2C CCH2CH2CH3 (d) None is correct
CH3
47. CH3
HBr
CH3C CHCH3   → A (predominant), A is:
CH3 OH
Br Br
(a) (H3C)3 CCHCH3 (b) (H3C)2 CCH(CH3)2

(c) both (a) and (b) (d) none is correct
48. H3 O+
HBr Mg/ether HCHO
CH3MgBr +  → A   → B  → C  +
→ D, D is
H3 O
(a) (b)
CH2OH
H3C CH2OH
CH3
OH
(c) (d)
CH3
CH3 CH2OH
49. Dipole moment of CH3CH2CH3 (I), CH3CH2OH (II) and CH3CH2F (III) is in order:
(a) I < II < III (b) I > II > III (c) I < III < II (d) III < I < II
50. Which has larger value of dipole moment?

(a) methanol (b) phenol
(c) equal (d) no dipole moment
+
H 3O
51. RMgBr + A  → CH3CH2CH2OH, R and A are:
(a) CH3CH2–– and HCHO (b) CH3–– and H2C CH2
O
(c) both are correct (d) none is correct
52. In the following case configuration about chiral C(*) is retained:

Me
(a) H * OH 
Na CH3 Br
→  →
Et
Me
CH3ONa
(b) H * OH 
TsCl
→  →
Et
Me
PCl5 CH3ONa
(c) H * OH  →  →
Et
(d) in none case
53. Which is hydrolysed at the fastest rate?

Cl
Cl
(a) CH3
(b) H C
3
Cl
(c) H C (d) Cl
2
54. HBO, oxymercuration-demercuration and acid catalysed hydration will give same
product in
CH2
(a) (b) CH2
H3C
CH3
(c) (d)

CPP - Alcohol Ether Phenol

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NAME: _______________________ BATCH: _______________ DATE: ______________

CHAPTER PRACTICE PROBLEMS

1. Which is hydrolysed to alcohol to a maximum extent?

2. In the following reaction, product formed:

3. In the following reaction, product formed:

4. Carbonyl compounds are reduced to alcohols by hydride reagents. This reduction

5. In the following reaction, B and C are respectively:

(a) HOH2C CH2OH

9. Which has maximum pKa value?

10. Isotopic O of I goes with:

13. Rate of hydration of

CH = CH2 CH = CHCH3 C = CH2

III: (CH3)3C – Cl + CH3ONa  → IV: (CH3)3C – ONa + CH3Cl  →

16. Which is the nucleophile in the following reaction?

17. Alkene can be converted to oxirane by oxidation using:

18. HI cleaves ether (A) forming:

(a) CH2OH, CH3I (b) CH2I, CH3OH

(c) CH2I, CH3I (d) CH2OH, CH3OH

19. Which is correct statement about following reaction?

20. Select correct statement for the following reaction:

21. In the following reaction, final product is:

22. Syn addition of diols takes place by using:

23. Boiling point of n-butanol is

24. Grignard reaction with the compound,

CO 2H is not possible, because

(c) CH3 C CH3 (d) Water

(c) H3 C C O C 2 H5 (d) No reaction

33. CH2 

(a) ONa + CH3CH2Br (b) Br + CH3CH2ONa

(c) OH + CH3CH2Cl (d) + H3O+ + CH3CH2Cl

(c) (d) no reaction

(c) both correct (d) none is correct

(c) CH2Cl (d) (C6H5)3CCl

(a) CH2 CHCH3 (b) CHCH2 CH3

(c) CHCHCH3 (d) CH2CH2CH2OH

40. H2C CH CH CH2 CH2 OH 

(c) H2C CH C CH2 CHO (d) H2C CH C CH2 C OH

41. CH2CH3 CH CH2

(a) (H3C)3 CCHCH3 (b) (H3C)2 CCH(CH3)2

50. Which has larger value of dipole moment?

52. In the following case configuration about chiral C(*) is retained:

53. Which is hydrolysed at the fastest rate?

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NAME: _______________ BATCH: _ DATE: ________