Title | Ch16 Organic Chemistry |
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Course | Chemistry |
Institution | College SA |
Pages | 110 |
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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
O
II
I
O O
O
V
IV
a) I b) II c) III d) IV e) V Answer: D Topic: Nomenclature 1
III
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
O
III
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
O
II
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 C 6H5 CH2 CH2CH 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
OH
II
I Ph
III
OH OH
OH
O
OH
O
Ph
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 Cl
Cl
III
O H H O Cl Cl
IV
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
NO 2
O2N
II
I
O
NO2
NO 2
O O2 N H
O2 N H NO 2
III
IV
O 2N
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
CH 2
C
C6 H5
OH
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? O2N
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
a) I b) II c) III d) IV e) V Answer: C 16
O
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?
O
III
O
II
I
O
O
V
IV
a) I b) II c) III d) IV 19
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?
O
III
O
II
I
O
O
V
IV
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) C6H5 MgBr + C6 H5C
O
O
b) HCN + c)
CH 3CCH3
O
H
+
HCN
H
d) CH 3C
+ xs CH3OH + HCl
O O
CH 3CHCH2COC 2 H5
e)
+ (i-Bu) 2 AlH
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 C6 H5 C N N CC 6H5 is produced by the reaction of an excess of benzaldehyde with which compound? a) Ammonia b) Hydrazine c) Nitrogen d) Phenylhydrazine e) Hydroxylamine 25
Answer: B Topic: Reagents Section: 16.8 Difficulty Level: Medium
53) The migratory aptitude for groups attached to a ketone or aldehyde carbonyl during the Baeyer-Villiger oxidation is: a) H >Ph- > 3° alkyl > 2° alkyl > 1° alkyl > methyl b) Ph- > H>3° alkyl>2° alkyl>1° alkyl>methyl c) 3° alkyl > 2° alkyl > 1° alkyl > methyl>H >Phd) 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph->H e) H > 3° alkyl > 2° alkyl > 1° alkyl > methyl>PhAnswer:A Topic: Mechanisms Section: 16.12 Difficulty Level: Medium
54) Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound? OH
a) C6 H5 CHOCH3 O
b) C6 H5COCH3 c) C6H5C(OCH3)3 OH
O
d) C6 H5 CHOCH3 and C 6H5COCH3 O
e) C6 H5COCH3 andC6H5C(OCH3)3 Answer: A Topic: Reaction Products Section: 16.7 Difficulty Level: Easy
55) Select the structure of the major product in the following reaction. 26
i) BH3 ii) H2O2,OH-, H2O
?
a) Ethylbenzene b) 1-Phenylethanol c) Acetophenone d) 2-Phenylethanal e) Vinylbenzene Answer: D Topic: Reaction Products Section: 16.4 Difficulty Level: Medium
56) Select the structure of the major product in the following reaction.
a) I b) II c) III d) IV e) V
27
Answer:D Topic: Reaction Products Section: 16.12 Difficulty Level: Medium
57) Select the structure of the major product in the following reaction. O
CH3COOOH
a) I b) II c) III d) IV e) V Answer:C Topic: Reaction Products Section: 16.12 Difficulty Level: Medium
58) Select the structure of the major product in the following reaction.
28
a) I b) II c) III d) IV e) V Answer:A Topic: Reaction Products Section: 16.12 Difficulty Level: Medium
59) Select the structure of the major product in the following reaction.
29
a) I b) II c) III d) IV e) V Answer:B Topic: Reaction Products Section: 16.12 Difficulty Level: Medium
60) Select the structure of the major product in the fo...