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chapter 16 test bank chem 200

Package Title: Solomons Test Bank
Course Title: Solomons 11e
Chapter Number: 16
Question type: Multiple Choice
1) What is the correct IUPAC name for the following compound?

O

a) 2-Methyl-5-heptanone
b) 7-Methyl-4-octanone
c) 6-Isopropyl-4-octanone
d) Isobutyl propyl ketone
e) 1,1-Dimethyl-4-heptanone
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
2) What is the correct structure for 7-methyl-4-octanone?
O

I


O

II

O

III
O

O

V

IV

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
1


Section: 16.2
Difficulty Level: Easy
3) What is the correct IUPAC name for the following compound?
O

a) 5,5-Dimethyl-2-heptanone
b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
c) 5-Ethyl-5-methyl- 2-hexanone
d) 5,5-Dimethyl-2-octanone
e) 3,3-Dimethyl-6-heptanone
Answer: A
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy


4) What is the correct structure for 5,5-dimethyl-2-heptanone?
O

O

I

O

II

O

III

H

O

V

IV

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
2


5) A correct name for the following compound would be which of those below?
O
H

a) 2,5-Dimethyl-6-hexanal
b) 2,5-Dimethylhexanal
c) 2-Aldehydoisohexane
d) 3,5-Dimethylheptanone
e) 1-Hydro-2,5-dimethyl-1-hexanone
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
6) What is the correct structure for 2,5-dimethylhexanal?
O

O

H

I

II

III

O

O

O

H

H

IV

V

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
7) What is the correct IUPAC name for the following compound?
3


O

a) 5,5-Dimethyl-2-heptanone
b) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
c) 5,5-Dimethylcycloheptanone
d) 4,4-Dimethylcycloheptanone
e) 3,3-Dimethylcycloheptanone
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
8) What is the correct IUPAC name for the following compound?
O

a) 2,4-dimethyl-2-pentenone
b) 2,5-dimethylcyclopenten-3-one
c) 2,4-dimethylcyclopent-2-enone
d) 3,5-dimethylcyclopent-2-enone
e) 2-methyl-5-methylcyclopent-2-enone
Answer: C
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
9) What is the correct IUPAC name for the following compound?

O

4


a) 1,1,2-Trimethyl-1,3-hexenone
b) 1,2-Dimethyl-1,3-hexenone
c) 2,3-Dimethyl-1,3-heptenone
d) 2,3-Dimethyl-2-hepten-4-one
e) 5,6-Dimethyl-5-hepten-4-one
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
10) What is the correct structure for 2,3-dimethyl-2-hepten-4-one?
O

I

O

II

O

III

O

IV

O

V

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
O

11) A correct name for C6H5CH2CH2CH is?
a) 3-Benzylpropanone
5


b) 3-Phenylpropanal
c) 3-Benzylpropanal
d) Nonanone
e) Nonanal
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
12) What is the correct structure for 3-phenylpropanal?
O

O
H

O

II

I

III
O

H
O

IV

V

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
13) What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?

6


O

Ph

Ph

OH

II

I
Ph

OH

O

III

OH
OH

OH

O

O

H

IV

V

O

Ph

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
14) Which is the proper name for the structure shown?
CHO
Cl
CH3

a) 2-Chloro-5-aldehydotoluene
b) 6-Chloro-3-aldehydotoluene
c) 2-Methyl-4-aldehydochlorobenzene
d) 4-Chloro-3-methylbenzaldehyde
e) 4-Methyl-5-chloro-2-benzaldehyde
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
15) What is the correct structure for 4-chloro-3-methylbenzaldehyde?
7

Ph


O

O

H

O

H

H

Cl

II

I

III

Cl

Cl
O

H
H
O
Cl

IV

Cl

V

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
16) What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?

8


NO2

O

O

H

O2N

NO2

II

I

O

NO2

NO2

O
O2N
H

O2N
H
NO2

III

IV

O2N

H

O
NO2

V

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

9


O

O

H

Cl

Cl

I

II
O

O

H

H

Cl

IV

III

Cl

Cl

O

H

V

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
18) What is the correct structure for 7-bromo-1-octyn-4-one?
Br

Br

Br

O

O

O

II

I

III

Br
Br

IV

O

V O

10


a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
19) What is the correct IUPAC name for the following compound?
Br

O

a)2-Methyl-2-bromobutanone
b)(S)-2-Bromo-2-methylcyclobutanone
c)(R)-2-Bromo-2-methylcyclobutanone
d) (S)-1-Bromo-1-methyl-2-cyclobutanone
e)(R)-1-Bromo-1-methyl-2-cyclobutanone
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
20) What is the correct IUPAC name for the following compound?

a)2-Bromobutanone
b)(S)-2-Bromo-cyclobutanone
c)(R)-2-Bromo-cyclobutanone
d) (S)-1-Bromo-2-cyclobutanone
e)(R)-1-Bromo-2-cyclobutanone
Answer:C
11


Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
21) What is the correct IUPAC name for the following compound?
O

Cl

H

a) (S)-3-chloro-1-hexanone
b) (S)-1-chloro-3-hexanone
c) (R)-3-chlorocyclohexanone
d) (S)-3-chlorocyclohexanone
e) (S)-1-chloro-3-cyclohexanone
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
22) What is the correct IUPAC name for the following compound?

a) (S)-3-chloro-1-hexanone
b) (S)-1-chloro-3-hexanone
c) (R)-3-chlorocyclohexanone
d) (S)-3-chlorocyclohexanone
e) (S)-1-chloro-3-cyclohexanone
Answer:C
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard

12


23) What is the correct IUPAC name for the following compound?

a) (1S, 4R)-bicyclo[2.2.1]hexan-2-one
b) (1S, 4R)-bicyclo[2.1.2]heptan-2-one
c) (1S, 4R)-bicyclo[2.2.1]heptan-2-one
d) (1R, 4S)-bicyclo[2.1.1]heptan-2-one
e) (1S, 4S)-bicyclo[2.1.2]heptan-2-one
Answer:C
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
24) What is the correct IUPAC name for the following compound?

a) bicyclo[1.1.0]butan-2-one
b) bicyclo[1.0.1]butan-2-one
c) bicyclo[1.1.0]pentan-2-one
d) bicyclo[0.1.1]butan-2-one
e) bicyclo[1.0.1]pentan-2-one
Answer:A
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
25) What is the correct IUPAC name for the following compound?

13


a) bicyclo[1.1.1]pentan-2-one
b) bicyclo[1.1.0]pentan-2-one
c) cyclopentanone
d) methylenepentan-2-one
e) bicyclo[1.0.1]pentan-2-one
Answer:B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
O
CH3

26) What is the IUPAC name for

CH

CH2

C

OH

C6 H5

a) 4-Oxo-5-phenyl-2-hexanol
b) 5-Hydroxy-2-phenyl-3-hexanone
c) 2-Hydroxy-5-phenyl-4-hexanone
d) 2-Hydroxypropyl-1-phenylethyl ketone
e) 5-Hydroxy-3-keto-2-phenylhexane
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
27) Which is the proper name for the structure shown?
O2 N

CH

O
NO2

a) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal
b) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal
c) 3-Methyl-5-(2,5-dinitrophenyl)pentanal
d) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde
e) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde
Answer: C
Topic: Nomenclature
14

CH3

?


Section: 16.2
Difficulty Level: Hard
28) Which is the proper name for the structure shown?
O
Cl

a) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal
b) 3-Methyl-5-(4-chlorophenyl)hexanol
c) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde
d) 3-Methyl-5-(4-chlorophenyl)-hexanaldehyde
e) 3-Methyl-5-(4-chlorophenyl)hexanal
Answer: E
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
29) Which is the proper name for the structure shown below?
Br
O

a) 7-Bromo-1,4-octynal
b) 7-Bromo-1,4-octynone
c) 2-Bromo-5,7-octynal
d) 7-Bromo-7-methyl-1-heptyne-3-ketone
e) 7-Bromo-1-octyn-4-one
Answer: E
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
30) What is the correct structure for (R)-7-bromo-1-octyn-4-one?

15


Br
Br

Br
O
O

O

II

I

III

Br
Br

IV

O

V O

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
31) What is the correct structure for (S)-7-bromo-1-octyn-4-one?
Br
Br

Br
O
O

O

II

I

III

Br
Br

IV

O

V O

a) I
b) II
c) III
d) IV
e) V
Answer: C
16


Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
32) Which is the IUPAC name for the structure shown below?
Br

H
O

a) (R)-5-Bromo-2-heptanal
b) (S)-5-Bromo-2-heptanal
c) (R)-5-Bromo-2-heptanone
d) (S)-5-Bromo-2-heptanone
e) (R)-3-Bromopentyl methyl ketone
Answer: C
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
33) Which is the IUPAC name for the structure shown below?
H

Br

O

a) (R)-5-Bromo-2-heptanal
b) (S)-5-Bromo-2-heptanal
c) (R)-5-Bromo-2-heptanone
d) (S)-5-Bromo-2-heptanone
e) (R)-3-Bromopentyl methyl ketone
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
34) What is the correct structure for (R)-5-bromo-2-heptanone?

17


Br

H

Br

Br

H

H

O

H

O

O

II

I

III

H

Br

H

H

Br

O

O

V

IV

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
35) What is the correct structure for (S)-5-bromo-2-heptanone?
Br

H

Br

Br

H

H

H

O

O

II

I

III

H

Br

H

H

Br

O

O

V

IV

18

O


a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
36) Which is the IUPAC name for the structure shown below?
O

a) 5-Cyclohexyl-2-hexanal
b) 5-Cyclohexyl-2-hexanone
c) 5-Cyclohexyl-5-methyl-2-pentanone
d) 5-(1-Methylcyclohexyl)-2-pentanone
e) 4-(1-Methylcyclohexyl)-2-butanone
Answer: E
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
37) What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

I

O

IV

III

O

II

V

O

a) I
b) II
c) III
d) IV
19

O

O


e) V
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
38) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

I

O

IV

III

O

II

V

O

O

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
39) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

a) I
b) II
20

O


c) III
d) IV
e) V
Answer: E
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
40) Which of the compounds listed below would you expect to have the highest boiling point?
(They all have approximately the same molecular weight.)
a)Pentane
b)1-Butanol
c)Butanal
d)1-Fluorobutane
e)Diethylether
Answer: B
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.3
Difficulty Level: Easy
41) Stereoisomers can exist in the case of which of the following?
a) The hydrazone of butanone
b) The oxime of acetone
c) The phenylhydrazone of cyclohexanone
d) The cyclic acetal formed from propanal and ethane-1,2-diol
e) The imine of cyclopentanone
Answer: A
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.8
Difficulty Level: Medium
42) Stereoisomers can exist in the case of which of the following?
a) The hydrazoneof benzophenone
b) The oxime of 2-methylcyclopentanone
21


c) The phenylhydrazone of 4-methylcyclohexanone
d) The imine of cyclopentanone
e) Two of these choices.
Answer: B
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.8
Difficulty Level: Medium
43) In which of the following reactions is the final product expected to be formed as a racemic
mixture?
H

a) C6H5MgBr + C6H5C

O

O

b) HCN +
c)

CH3CCH3

O

H

+

HCN

H

d) CH3C

+ xs CH3OH + HCl

O
O

CH3CHCH2COC2H5

e)

+ (i-Bu)2AlH

CH3

Answer: C
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.9
Difficulty Level: Medium
44)Acetals are unstable in the presence of an aqueous solution of which of these?
a) HCl
b) NaOH
c) KHCO3
d) Na2CO3
e) NaCl
22


Answer: A
Topic: Reagents
Section: 16.7
Difficulty Level: Easy
45) LiAlH4 (LAH) cannot be used to convert carboxylic acids to the corresponding aldehydes
because:
a) LAH is not sufficiently reactive.
b) RCOOH is converted into RCOOLi.
c) RCOOH is reduced to RCH2OH.
d) RCOOH is reduced to RCH3.
e) RCOOH is converted into R2C=O.
Answer: C
Topic: Reagents
Section: 16.4
Difficulty Level: Easy
46) Identify the reagent(s) that would bring about the following reaction:
CH3CH2CH2COCl ⎯⎯⎯→

CH3CH2CH2CHO

a) H2/Ni
b) Li/liq.NH3
c) LiAlH[OC(CH3)3]3, ether
d) NaBH4, CH3OH
e) LiAlH4, ether
Answer: C
Topic: Reagents
Section: 16.4
Difficulty Level: Easy
47) Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group
of an aldehyde or ketone?
a) Ib) H3O+
23


c) AlCl3
d) BF3
e) ZnCl2
Answer: A
Topic: Reagents
Section: 16.6
Difficulty Level: Easy
48) Which reagent(s) could be used to carry out the following transformation?
O

?

a) Zn(Hg), HCl, reflux
b) LiAlH4, ether
c) HSCH2CH2SH, BF3; then Raney Ni (H2)
d) All of these choices.
e) Two of these choices.
Answer: E
Topic: Reagents
Section: 16.7
Difficulty Level: Medium
49) The following reduction can be carried out with which reagent(s)?

?
O

a) Zn(Hg), HCl
b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
c) H2NNH2, KOH
d) None of these choices.
e) All of these choices.
Answer:E
Topic: Reagents
Section: 16.7
24


Difficulty Level: Medium
50) The following reduction can be carried out with which reagent(s)?

?
O

a) Zn(Hg), HCl
b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
c) NaBH4, CH3OH
d) Zn(Hg), HCl and i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
e) Zn(Hg), HCl and NaBH4, CH3OH
Answer: D
Topic: Reagents
Section: 16.7
Difficulty Level: Medium
51) Which reagent will not differentiate between 3-butenal and 2-butanone?
a) Br2/CCl4
b) Ag2O,OHc) H2NNHC6H5
d) KMnO4,OHe) None of these choices.
Answer: C
Topic: Reagents
Section: 16.8
Difficulty Level: Medium
H

H

52) The compound C6H5C N N CC6H5 is produced by the reaction of an excess of
benzaldehyde with which compound?
a) Ammonia
b) Hydrazine
c) Nitrogen
d) Phenylhydrazine
e) Hydroxylamine
25


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