Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 1 of 26

1. What is the relationship between alcohols I and II?

CH3
OH

CH3

HO

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

2. What is the relationship between alcohols I and II?

CH3 CH3

OH
OH

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 2 of 26

3. What is the relationship between alcohols I and II?

H H

CH3 CH3
OH H

H OH
I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

4. What is the correct IUPAC name for the following compound?

CH3
CH3CH2C=CCH2CH3
CH2CH2OH
A) 3-methyl-4-ethyl-3-hexen-6-ol
B) 4-ethyl-3-methyl-3,6-hexenol
C) 3-ethyl-4-methyl-3-hexen-1-ol
D) 3-methyl-4-(2-hydroxyethyl)-3-hexene
E) 3-(2-hydroxyethyl)- 3-methyl-3-hexene

5. Which of the following can be described as “optically active, primary alcohol”?

A) CH3CH2CH2CH2CH2OH
B) (CH3)2CHCH2CH2OH
C) CH3CH2CH(CH3)CH2OH
D) (CH3)2CHCHOHCH3
E) Two of the above
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 3 of 26

6. OH

OH

is properly named:
A) 1,2-Cyclohexanediol
B) 1,6-Cyclohexanediol
C) (1R,2R)-1,2-Cyclohexanediol
D) (1R,2S)-1,2-Cyclohexanediol
E) (1S,2S)-1,2-Cyclohexanediol

7. The number of secondary alcohols corresponding to the formula C5H12O, counting

stereoisomers separately, is:
A) 1
B) 2
C) 3
D) 4
E) 5

8. Which compound would have the highest boiling point?

A) CH3CH2CH2CH3
B) CH3CH2OCH3
C) CH3CH2CH2OH
D) (CH3)2CHOH
E) HOCH2CH2OH

9. Which compound would have the greatest solubility in water?

A) Diethyl ether
B) Methyl propyl ether
C) 1-Butanol
D) 1,2-Butanediol
E) Pentane
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 4 of 26

10. Which product(s) would you expect to obtain from the following sequence of reactions?
CH3
1. BH3-THF
?
2. H2O2, NaOH

CH3 CH3 H3C CH2OH

CH3 O
OH OH
OH

+ + +
enantiomer enantiomer enantiomer

I II III IV V
A) I
B) II
C) III
D) IV
E) V

11. Select the structure of the major product formed from the following reaction.

CH3 1. Hg(OOCCH3)2
THF, H2O
?
2. NaBH4, NaOH

CH3 CH3 CH2OH HO CH3 CH3

OH

OH
OH

I II III IV V
A) I
B) II
C) III
D) IV
E) V
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 5 of 26

12. Anti-Markovnikov hydration of the carbon-carbon double bond occurs when an alkene
reacts with:
A) BH3:THF; then H2O2/OH-
B) BH3:THF; then CH3COOH
C) Hg(OAc)2, THF, H2O; then NaBH4, OH-
D) Hg(OAc)2, THF, CH3OH; then NaBH4, OH-
E) Hg(OAc)2, THF, H2O; then BH3:THF

13. Which would be the best way to carry out the following synthesis?
?
CH3CH2CHCH3 CH3CH2CH2CH2OH

Br
A) (1) HA, heat; (2) H3O+, H2O, heat
B) (1) (CH3)3COK / (CH3)3COH; (2) BH3:THF, then H2O2, OH-
C) (1) (CH3)3COK / (CH3)3COH; (2) H3O+, then H2O, heat
D) (1) KOH, C2H5OH; (2) BH3:THF, then H2O2, OH-
E) (1) KOH, C2H5OH; (2) HA, heat; (3) H3O+, H2O, heat

14. Which reaction can accomplish the following transformation in good yield:
?

OH
A) H+/H2O
B) oxymercuration/demercuation
C) hydroboration/oxidation
D) Reaction with NaOH
E) None of the above
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 6 of 26

15. Select the structure of the major product formed from the following reaction.
H3O+
?

OH

OH

OH
II III
I

OH

OH

V
IV
A) I
B) II
C) III
D) IV
E) V

16. Select the structure of the major product formed from the following reaction.
H3O+
?

OH

OH

OH
II III
I

OH

OH
IV
IV
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 7 of 26

A) I
B) II
C) III
D) IV
E) V

17. Which of these alkyl halide syntheses is predicted to occur at the greatest rate?
A) CH3CH2CH2CH2OH + HI 
B) (CH3)2CHCH2OH + HBr 
C) CH3CHOHCH2CH3 + HCl 
D) CH3CHOHCH2CH3 + HBr 
E) (CH3)3COH + HI 

18. The following reaction,

HBr
CH3CH2CH2CH2OH CH3CH2CH2CH2Br + H2O
heat
is probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.

19. Which of the following could be used to synthesize 1-bromopentane?

A) CH3CH2CH2CH=CH2 + HBr 
B) CH3CH2CH2CH2CH2OH + PBr3 
C) CH3CH2CH2CH2CH2OH + NaBr 
D) CH3CH2CH2CH2CH2OH + Br2 
E) CH3CH2CH2CH=CH2 + Br2 
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 8 of 26

20. What would be the major product of the following reaction sequence?

OH
H
pCH3C6H4SO2Cl NaI
tosylate ?
base ethanol
CH3
H

I H H H
H I I SO2C6H4CH3

CH3 CH3 CH3 CH3

H H I H
I II III IV
A) I
B) II
C) III
D) IV
E) An equimolar mixture of I and II
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 9 of 26

21. The major product of the following reaction would be:

CH3
H OH CH3SO2Cl CH3CO2-
Product ?
base
C2H5

CH3 CH3 CH3

H3CCO2 H H O2CCH3 H3CCO2 OSO2CH3

C2H5 C2H5
C2H5

I II III
A) I
B) II
C) III
D) Equal amounts of I and II
E) None of these

X 22. The product(s) of the following reaction

1 equiv. HI
is/are:
1 equiv.
heat HI is/are:
O heat
O

O
and I
OH
and
IO OH II I

I II I
I
I
I OH
OH O
III IV
O
III IV
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 10 of 26

A) I
B) II
C) III
D) IV
E) None of these

X
23. What would be the major product(s) of the following reaction

O 1 equiv. HBr(conc)
?
heat

A) C6H5Br + CH3OH
B) C6H5CH2Br + CH3Br
C) C6H5CH2OH + CH3Br
D) C6H5CH2Br + CH3OH
E) C6H5CH2CH2Br
Ans: D

24. What would be the major product of the following reaction sequence?
O

H+
?
CH3OH

OH OCH3 OH OH OH
OCH3 OCH3 OCH
3

I II III IV
A) I
B) II
C) III
D) IV
E) Equal amounts of II and IV
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 11 of 26

25. What is the correct IUPAC name for the following compound?
O

O
A) 15-crown-5
B) 15-crown-4
C) 5-crown-15
D) 15-crown-15
E) Cyclopentadecane pentaether

26. Propose a structure for the compound with the following formula that is consistent with the
IR and 1H NMR data shown:

C7H8O

IR – 3325cm−1, strong, broad

1H broad singlet at 2.3  (exchangeable)
2H singlet at 4.6 
5H multiplet at 7.3 

:
A) Benzyl Alcohol
B) 4-methyl phenol
C) 3-methyl phenol
D) 1-phenyl ethanol

Chapter 12

27. When nucleophilic addition to a carbonyl group occurs, the carbon attacked undergoes
this hybridization change:
A) sp2  sp3
B) sp  sp2
C) sp  sp3
D) sp3  sp2
E) sp2  sp
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 12 of 26

28. The following transformation would be considered a(n)?

A) reduction
B) oxidation
C) addition
D) elimination
E) rearrangement

29. Which product is formed from the following transformation:

O
1. LAH
O ?
2. H3O+
A)
O

OH

B)
HO
OH
C)

D)
H

HO
O
E)
O

OCH3

30. List the following compounds in order of increasing level of oxidation:

 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 13 of 26

OH O

II III
I

A) I, II, III
B) I, III, II
C) II, I, III
D) III, II, I
E) III, I, II

31. List the following alkyl halides in order of increasing ease of Grignard formation:
RBr RCl RI RF

I II III IV
A) I, II, III, IV
B) III, I, II , IV
C) IV, II, I, III
D) III, I, IV, II
E) I, IV, III, II

32. Which of the reagents listed below would efficiently accomplish the transformation of
CH3CH2CH=CHCH2CH2CHO into CH3CH2CH2CH2CH2CH2CH2OH?
A) KMnO4
B) NaBH4
C) Br2 in CCl4
D) H2, Ni
E) Two of the above
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 14 of 26

33. Which of these compounds will not be reduced by LiAlH4?

A) CH3CH2CH2CH=CH2
B) H

CH3CH2CH2C O
C) O

CH3CH2CH2COH
D) O

CH3CH2CH2COCH3
E) O

CH3CH2CH2CCH3

X
34. Which of these compounds cannot be reduced by sodium borohydride?
A) H

(CH3)2CHC O
B) O

CH3CH2CCH3
C) O

C6H5COH
D) O

CH3(CH2)4COCH3
E) Neither C) nor D) can be reduced.

35. Predict the product(s) of the following reaction:

O

1. LiAlH4
?
2. H3O+
H CH3

OH OH OH OH

H H CH3 CH3
CH3 CH3 H H

H CH3 H3C H H CH3 H3C H

III IV
I II
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 15 of 26

A) A mixture of I and II
B) A mixture of I and III
C) A mixture of II and III
D) A mixture of II and IV
E) A mixture of III and IV

36. Which of the reagents listed below would efficiently accomplish the transformation of
CH3CH2CH=CHCH2CH2CHO into CH3CH2CH=CHCH2CH2CH2OH?
A) KMnO4
B) NaBH4
C) Br2 in CCl4
D) H2, Ni
E) Two of the above

37. What would be the major product of the following reaction?

O i) NaBH4
A
ii) ethylene oxide, HA

OH O HO O
O O OH

I II III
O
HO O OH
OH
IV V
A) I
B) II
C) III
D) IV
E) V

38. What is the predominant product from the reaction of 2-hexanol with PCC in CH2Cl2?
A) CH3CO2H
B) CH3(CH2)3CO2H
C) O

CH3(CH2)3CCH3
D) CH3(CH2)4CO2H
E) A) and B)
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 16 of 26

39. CrO3 in H2SO4/H2O will fail to give a positive test with which of these compounds?
A) CH3CH2CH2CH2OH
B) CH3CHCH2CH3

OH
C) (CH3)3COH
D) H

CH3CH2CH2C O
E) More than one of these

40. Which reagent(s) will distinguish between 2-methylcyclopentanol and 1-

methylcyclopentanol?
A) Br2/CCl4
B) KMnO4
C) CrO3/aqueous H2SO4
D) NaOH (aq)
E) B) and C)

41. Which of the reagents listed below would serve as the basis for a simple chemical test to
distinguish between (CH3)2C=CHCH2CH2OH and (CH3)2CHCH2CH2CH2OH ?
A) CrO3 in H2SO4
B) Cold conc. H2SO4
C) Br2 in CCl4
D) NaOH/H2O
E) NaBH4

42. Which of the reagents/techniques listed below would serve as the basis for a simple
chemical test to distinguish between 2-methyl-3-hexyn-1-ol and 2-methyl-5-hexyn-1-ol?
A) CrO3 in H2SO4
B) Cold conc. H2SO4
C) Br2 in CCl4
D) NaBH4
E) IR spectroscopy
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 17 of 26

43. The final product, D, in the following reaction sequence,

CH2 CH2

CH3CHOH PBr3 Mg O H3O+

A B C D
ether
CH3
, would be?
A) CH3CHOCH2CH2OH

CH3
B) CH3CHCH2CH2Br

CH3
C) CH3CHCH2CH2OH

CH3
D) CH3CHOCH2CH3

CH3
E) CH3CHCH2CH3

CH3
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 18 of 26

44. What is the product, A, that would be obtained from the following reaction sequence?

CH3CH2MgBr CH3CH CHCH3 H3O+

C CH A

CH3 CH3 CH3 CH3

C CCH2CH3 C CCH CHOCH2CH3 CH3CH2 C CCH CHOH

I II III

CH3 CH3 CH3

C CCH CHOH C C O CHCH2CH3

IV V
A) I
B) II
C) III
D) IV
E) V

45. The final product, E, in the following reaction sequence is,

O
PBr3 Mg H3O+ PCC
OH A B C D E
ether CH2Cl2

OH
H
I OH II III
O O

OH
V
IV
A) I
B) II
C) III
D) IV
E) V
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 19 of 26

46. The final product, E, in the following reaction sequence is,

PBr3 Mg CH2O H3O+ PCC
OH A B C D E
ether CH2Cl2

OH

H
OH
I II III
O
O

IV O V
A) I
B) II
C) III
D) IV
E) V

47. What would be the final product, A, in the following reaction sequence?
O
OH PBr3 Mg, Et2O H3O+
A
heat

OH
O OH

I II III
Br
O
OH

IV V
A) I
B) II
C) III
D) IV
E) V

48. Predict the product(s) of the following reaction:

Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 20 of 26

1. PhMgBr
H ?
2. H3O+
H CH3

OH OH OH OH

H H Ph Ph
Ph Ph H H

H CH3 H3C H H CH3 H3C H

I II III V

A) A mixture of I and II
B) A mixture of I and III
C) A mixture of II and III
D) A mixture of II and IV
E) A mixture of III and IV

49. In which of the following series are the compounds arranged in order of decreasing
basicity?
A) CH3CH2MgBr > NaNH2 > HCCNa > NaOH > CH3CH2ONa
B) CH3CH2MgBr > NaNH2 > HCCNa > CH3CH2ONa > NaOH
C) HCCNa > CH3CH2MgBr > NaNH2 > CH3CH2ONa > NaOH
D) NaNH2 > CH3CH2MgBr > HCCNa > CH3CH2ONa > NaOH
E) None of these

50. C6H5

CH3CH2CH2CCH3

Your task is to synthesize OH through a Grignard synthesis. Which pairs

of compounds listed below would you choose as starting materials?
A) O

CH3CH2CH2Br and CH3CC6H5

B) O

CH3CH2CH2CH and C6H5Br

C) O CH3CH2CHCH3
and
C6H5CH Br
D) More than one of these
E) None of these
Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 21 of 26

51. Your task is to synthesize 2-phenyl-2-hexanol through a Grignard synthesis. Which

pair(s) of compounds listed below would you choose as starting materials?
A) O

and
Br

B) CH3CHCH2Br O
and
CH3 CH3CC6H5
C) O

CH3CH2CH2CH2CCH3 and C6H5Br

D) Answers A) or B)
E) Answers A) or C)

52. What is the product, A, that would be obtained from the following reaction sequence?

CH3CH2MgBr H3O+
C CH A

C CCH2CH3 C C
C C
OH
O

II III
I

C C C C O

OCH3

IV V
A) I
B) II
C) III
D) IV
E) V
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 22 of 26

53. What is the product, A, that would be obtained from the following reaction sequence?

NaNH
CH 3CH2MgBr
2 CH3CH CHCH3 H3O+
C CH A

CH3 CH3 CH3 CH3

C CCH2CH3 C CCH CHOCH2CH3 CH3CH2 C CCH CHOH

I II III

CH3 CH3 CH3

C CCH CHOH C C O CHCH2CH3

IV V
A) I
B) II
C) III
D) IV
E) V

54. Which free radical would be most stable?

A)

B)

C)
D)

E)
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 23 of 26

55. Which free radical would be most stable?

II III IV V
I
A) I
B) II
C) III
D) IV
E) V

56. I

II

V III

IV
Which hydrogen atom(s) of is/are most susceptible to abstraction
by free radicals?
A) I
B) II
C) III
D) IV
E) V

X
57. CH3

CH3 CH CH2 CH CH2

Which carbon of V IV III II I is predicted to be the major site of

substitution when this alkene reacts with chlorine at 400C?
A) I
B) II
C) III
D) IV
E) V

X
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 24 of 26

58. An unsaturated product results from the reaction of cyclohexene with which of these?
A) Br2/CCl4 at 25C
B) NBS/CCl4, ROOR
C) HCl, ROOR
D) HCl, no peroxides
E) More than one of these

59. Treatment of 2-butene (cis or trans) with Cl2 at 400C would yield mainly:
A) CH2ClCHClCH2CH3
B) CH3CHClCH2CH3
C) CH3CH=CClCH3
D) CH3CH=CHCH2Cl and CH3CHClCH=CH2
E) CH3CHClCHClCH3

60. Treatment of 2-butene (cis or trans) with N-bromosuccinimide in CCl4 would yield
mainly:
A) CH3CHBrCHBrCH3 alone
B) CH3CH=CBrCH3 alone
C) CH3CH=CHCH2Br alone
D) CH2BrCH2CH=CH2 and CH3CH=CHCH2Br
E) CH3CHBrCH=CH2 and CH3CH=CHCH2Br

X
61. Which carbocation would be most stable?
A)

B)

C)

D)

E)

X
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 25 of 26

62. Which carbocation would be most stable?

CH2 CH3 CH3 CH3 CH3

I II III IV V
A) I
B) II
C) III
D) IV
E) V

Which is not an example of resonance?

63.

I CH2=CHCH2 . . CH2CH=CH2

+
II CH2 CH2

CH2 CH3
III +
+

. .
IV CH2=CHCHCH2CCl3 CH2CH=CHCH2CCl3

A) I
B) II
C) III
D) IV
E) None of these are examples of resonance.

X
 Practice questions Chapter 11, 12 and 13 Name: _______________ Date: ___ Page 26 of 26

64. Select the structure(s) of the conjugated diene(s).

I II III

IV V
A) I and II
B) II and III
C) III and IV
D) I, II and V
E) V

X
65. Which of the following dienes is a cumulated diene?
A) CH2=CHCH2CH2CH=CH2
B) CH2=CHCH=CHCH2CH3
C) CH3CH=C=CHCH2CH3
D) CH3CH=CHCH=CHCH3
E) CH3CH=CHCH2CH=CH2

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