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Package title: Solomons Test Bank Course Title: Solomons 12e Chapter Number: 8

Question type: Multiple choice

1) The thermodynamic parameters at 298 K for the following reaction are given below. gas phase CH3 CH2Cl CH2=CH2 + HCl Hº = -64.9 kJ mol-1  Sº = -131 J K-1 mol-1  Gº = -25.8 kJ mol-1 Which of the following statements is true of the reaction? A) Both Hº and Sº favor product formation. B) Neither Hº nor Sº favors product formation. C) The entropy term is unfavorable but the formation of ethyl chloride is favored. D) The entropy term is favorable but the formation of ethyl chloride is not favored. E) The sign of Gº indicates that the reaction cannot occur as written. Answer: C Topic: General Information Section: 8.1 Difficulty Level: Medium

2) The interaction of the  bond of an alkene with an electrophile can initially result in the formation of a species termed a  complex. Which of these cannot combine with an alkene to form a  complex? A) H+ B) NH3 C) Ag+ D) Hg2+ E) BF3 Answer: B Topic: Reaction Products Section: 8.1 Difficulty Level: Easy

1

3) Markovnikov addition of HI to 2-methyl-2-butene involves: A) initial attack by an iodide ion. B) initial attack by an iodine atom. C) isomerization of 2-iodo-2-methylbutene. D) formation of a carbocation at C-2. E) formation of carbocation at C-3. Answer: D Topic: Reaction Products Section: 8.2 Difficulty Level: Easy

4) What is the major product for the following reaction? HI

I

A)

+ enantiomer

B)

I

+ enantiomer

C)

I I

+ enantiomer

D) I

+ enantiomer

E) Answer: A Topic: Reaction Products Section: 8.2 Difficulty Level: Easy

5) What would be the major product of the following reaction? 2

HCl

Cl

Cl

Cl

Cl

I

II

III

Cl Cl

IV

V

A) I B) II C) III D) IV E) V Answer: B Topic: Reaction Products Section: 8.2 Difficulty Level: Easy

6) Treating 1-methylcyclohexene with HCl would yield primarily which of these? H3C

H 3C

Cl

Cl

I

H 3C Cl

II H 3C

Cl

IV

III Cl

V

A) I B) II C) III D) IV E) V Answer: C Topic: Reaction Products 3

Section: 8.2 Difficulty Level: Easy

7) How many compounds are possible from the addition of bromine to CH2=CHCH2CH3 (counting stereoisomers separately)? A) One B) Two C) Three D) Four E) Five Answer: B Topic: Reaction Products Section: 8.2 Difficulty Level: Easy

8) (R)-3-Chloro-1-butene reacts with HCl by Markovnikov addition, and the products are separated by gas chromatography. How many total fractions would be obtained and how many would be optically active? A) one optically active fraction only B) one optically active fraction and one optically inactive C) two optically active fractions D) one optically active fraction and two optically inactive E) two optically active fractions and one optically inactive Answer: B Topic: Reaction Products Section: 8.2 Difficulty Level: Medium

9) What is the major product for the following reaction? HBr

+ enantiomer

A)

Br

4

+ enantiomer Br Br

B)

+ enantiomer

C) + enantiomer Br

D) Answer: C

Topic: Reaction Products Section: 8.2 Difficulty Level: Medium

10) What is the major product for the following reaction? HCl

A)

Cl

Cl

B)

C)

Cl

Cl

D) Cl

E) Answer: E Topic: Reaction Products Section: 8.2 Difficulty Level: Medium 5

11) What is the major product for the following reaction? HBr

A)

Br Br

B) + enantiomer

C)

Br Br

D) Answer: D Topic: Reaction Products Section: 8.2 Difficulty Level: Medium

12) What product would you expect from addition of deuterium chloride to 2-cyclohexyl-4methyl-2-pentene? Cl

D

D Cl

D H

Cl

I

III

II Cl

D

D Cl

IV

V

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

6

Answer: B Topic: Reaction Products Section: 8.2 Difficulty Level: Medium

13) Addition of hydrogen chloride to the following molecule would produce: HCl ? Cl Cl

Cl

Cl

Cl Cl

Cl

Cl

Cl

Cl

Cl

I

II

III

IV

V

A) I and II B) II and III C) I and IV D) V E) All of these choices are equally likely to be formed. Answer: A Topic: Reaction Products Section: 8.2 Difficulty Level: Medium

14) Consider the addition of HCl to 3-methyl-1-butene. The major product of the reaction would be: A) 1-Chloro-2-methylbutane B) 1-Chloro-3-methylbutane C) 2-Chloro-2-methylbutane D) 2-Chloro-3-methylbutane E) 1-Chloropentane Answer: C Topic: Reaction Products Section: 8.2 Difficulty Level: Medium

15) What are possible products for the following reaction? 7

HBr

Br

A) Br

+ enantiomer

B) Br

C) Answer: B and C Topic: Reaction Products Section: 8.2 Difficulty Level: Hard

16) What are the major product(s) formed by treating methylcyclopentene with HBr and MeOOMe?

A) I B) II C) III Answer: C Topic: Reaction Products Section: 8.2 Difficulty Level: Medium

8

17) What is the major product of the following reaction sequence? 1. HBr 2. NaCN, DMSO

CN

A)

B)

C)

CN

+ enantiomer

CN

+ enantiomer

Cl

CN

D) E) None of these choices. Answer: E Topic: Reaction Sequences Section: 6.5, 8.2 Difficulty Level: Medium

18) What is the major product of the following reaction sequence? 1. HI 2. t-BuOK, t-BuOH

A) B)

C)

D) Answer: B 9

Topic: Reaction Sequences Section: 7.6, 8.2 Difficulty Level: Medium

19) What is the major product of the following reaction sequence? 1. HCl 2. t-BuOK, t-BuOH

A)

B)

C)

D)

O

E) Answer: C

Topic: Reaction Sequences Section: 7.6, 8.2 Difficulty Level: Medium

20) What is the major product of the following reaction sequence? Cl

1. t-BuOK, t-BuOH 2. HBr Br

A)

10

Br Br

B)

C)

Br

Br

D) E) None of these choices. Answer: C Topic: Reaction Sequences Section: 7.6, 8.2 Difficulty Level: Medium

21) In general, when the addition of an unsymmetrical electrophilic reagent to an unsymmetrical alkene forms the product predicted by Markovnikov's rule, that occurs because: A) the product is statistically favored. B) steric hindrance favors its formation. C) it is formed via the more/most stable carbocation. D) it is the more/most stable product. E) All of these choices are reasons. Answer: C Topic: Reaction Products Section: 8.2 Difficulty Level: Easy

22) What is the chief product of the reaction of IBr with 2-methyl-2-pentene? A) 2-bromo-3-iodo-2-methylpentane B) 3-bromo-2-iodo-2-methylpentane C) 1-bromo-2-iodo-2-methylpentane D) 2-bromo-1-iodo-2-methylpentane E) All of these choices. Answer: A Topic: Reaction Products Section: 8.2 11

Difficulty Level: Medium 23) Treating 1-methylcyclohexene with H3O+ would yield primarily which of these? HO

HO HO

I

II

III

HO OH

IV

V

A) I and V B) II C) III and V D) IV E) I, III, and V Answer: D Topic: Reaction Products Section: 8.4 Difficulty Level: Easy

24) What is the product(s) formed by treating 3,3 dimethylcyclopentene with H3O+ and heating?

A) I only B) II and IV C) I and III D) IV and V E) none of these choices 12

Answer: B Topic: Reaction Products Section: 8.4 Difficulty Level: Easy

25) Which product would you expect from the following reaction? H3 O+ H2 O

OH OH

II

I

OH

III

OH

IV

V

A) I B) II C) III D) IV E) V Answer: D Topic: Reaction Products Section: 8.4 Difficulty Level: Easy

26) What is the chief product of the acid-catalyzed hydration of 2,5-dimethyl-2-hexene? A) 2,5-dimethyl-1-hexanol B) 2,5-dimethyl-2-hexanol C) 2,5-dimethyl-3-hexanol D) 2,5-dimethyl-2,3-hexanediol E) 2,5-dimethyl-3,4-hexanediol Answer: B

13

Topic: Reaction Products Section: 8.4 Difficulty Level: Easy

27) Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following? A) (CH3)2C(OH)CH2CH3 B) CH2OHCH(CH3)CH2CH3 C) (CH3)2CHCHOHCH3 D) (CH3)2CHCH2CH2OH E) CH3CH2CH(CH3)CH2OH Answer: A Topic: Reaction Products Section: 8.4 Difficulty Level: Easy

28) When either cis- or trans-2-butene is treated with hydrogen chloride in ethanol, the product mixture that results includes: A) CH3CH2CH2CH2Cl B) CH3CH2CH2CH2OCH2CH3 C) CH3CH2CH(CH3)OCH2CH3 D) (CH3)3CCl E) (CH3)2CHCH2OCH2CH3 Answer: C Topic: Reaction Products Section: 8.4 Difficulty Level: Medium

29) Which alkene would you expect to be most reactive toward acid-catalyzed hydration? A) 1-pentene B) trans-2-pentene C) cis-2-pentene D) 2-methyl-1-butene E) All of these would be equally reactive. Answer: D

14

Topic: General Information Section: 8.4 Difficulty Level: Medium

30) What is the major product for the following reaction? a. Hg(OAc)2, H 2O b. NaBH4 , NaOH

A) OH

+ enantiomer

B)

C)

OH HO

D) Answer: B Topic: Reaction Products Section: 8.5 Difficulty Level: Easy

31) What is the product(s) formed by treating 3,3 dimethyl-1-cyclopentene with Hg(OAc)2 in THF/water followed by treatment with NaBH4 in NaOH(aq)?

15

A) I only B) II and IV C) I and III D) IV and V E) none of these choices Answer: C Topic: Reaction Products Section: 8.5 Difficulty Level: Easy

32) What is the major product for the following reaction? a. Hg(OAc)2, H2O b. NaBH4, NaOH O H O

A)

+ enantiomer

B)

OH OH

C) 16

+ enantiomer OH D) E) None of these choices.

Answer: C Topic: Reaction Products Section: 8.5 Difficulty Level: Easy

33) What is the major product for the following reaction? a. Hg(OAc)2 , H2 O b. NaBH4 , NaOH OH

+ enantiomer

A) OH

+ enantiomer OH

B) OH

+ enantiomer

C) + enantiomer

D)

HO OH

+ enantiomer

E) Answer: D Topic: Reaction Products Section: 8.5 Difficulty Level: Medium 17

34) What is the major product for the following reaction?

+ enantiomer O

A)

+ enantiomer

B)

O OH

C) O

D) E) None of these choices. Answer: D Topic: Reaction Products Section: 8.5 Difficulty Level: Medium

35) What is the major product for the following reaction?

A)

O O

B) 18

O

C) HO

+ CO2 O

D) HO

E) Answer: B Topic: Reaction Products Section: 8.5 Difficulty Level: Medium

36) What is the major product of the following reaction sequence?

OCH 3

A)

OH

B) OCH 3

C) OH

D) Answer: A Topic: Reaction Sequences Section: 6.16, 8.5 Difficulty Level: Medium

19

37) What is the major product of the following reaction sequence? 1. H2, Pd/CaCO 3 , quinoline

2a. Hg(OAc)2, H 2O 2b. NaBH4, NaOH

A)

B)

C)

OH

OH

O HO

D) HO

E) Answer: B Topic: Reaction Sequences Section: 7.15, 8.5 Difficulty Level: Medium

38) What is the major product of the following reaction sequence? 1. EtOH, EtONa, heat 2a. BH 3:THF 2b. H2 O2 , NaOH

Cl

A) HO + enantiomer

B)

OH

20

+ enantiomer

C)

OH

D) Answer: C Topic: Reaction Sequences Section: 6.16, 8.6, 8.7, 8.8 Difficulty Level: Medium

39) What is the major product of the following reaction sequence? 1. H2, Pd/CaCO3 , quinoline 2a. BH3 :THF 2b. H 2O 2, NaOH

OH

A)

H

B)

O

C) HO

D)

E)

OH

Answer: E Topic: Reaction Sequences Section: 7.15, 8.6, 8.7, 8.8 Difficulty Level: Medium

40) What is the major product of the following reaction sequence? 21

Br

1. EtOH, EtONa, 60 oC 2a. O 3, CH2 Cl2, -78 oC 2b. Me 2S

O O

A) CHO

CHO

B) OH OH + enantiomer

C) O CHO

D) Answer: D Topic: Reaction Sequences Section: 6.16, 8.7, 8.8, 8.9 Difficulty Level: Medium

41) Which of the following would be produced upon ozonolysis of camphene?

22

A) I, II, V B) II, III C) I, V D) II, V E) III, IV Answer: C Topic: Reaction Product Section: 8.9 Difficulty Level: Medium

42) What is the major product of the following reaction sequence? Br

1. EtOH, 70 o C 2a. O 3, CH 2 Cl2, -78 o C 2b. Me 2S

O

A)

O

23

OH

OH

B) O

C)

O CHO

CHO D) E) None of these choices.

Answer: A Topic: Reaction Sequences Section: 6.17, 8.7, 8.8, 8.9 Difficulty Level: Medium

43) What is the major product for the following reaction? a. BH3:THF b. H2O2, NaOH OH

+ enantiomer

A)

B)

C)

OH H

+ HCHO

D)

O

24

OH

E) Answer: E

Topic: Reaction Products Section: 8.6, 8.7, 8.8 Difficulty Level: Easy

44) What is the major product for the following reaction? a. BH 3:THF b. H2 O 2, NaOH HO

A) O

+ CO2 OH

B) C) OH

+ enantiomer

D) OH

+ enantiomer

OH

E) Answer: A

Topic: Reaction Products Section: 8.6, 8.7, 8.8 Difficulty Level: Easy

45) What is the major product for the following reaction? a. BH3:THF b. H2O2, NaOH HO

A) 25

HO

+ enantiomer

B) HO

+ enantiomer

C) OH

+ enantiomer

D) Answer: B Topic: Reaction Products Section: 8.6, 8.7, 8.8 Difficulty Level: Medium

46) What is the major product for the following reaction? a. BH 3:THF b. H 2O 2 , NaOH + enantiomer OH OH

A)

O H O

B)

+ enantiomer

C)

OH

D)

OH

+ enantiomer

E) OH Answer: E 26

Topic: Reaction Products Section: 8.6, 8.7, 8.8 Difficulty Level: Medium

47) What is the major product for the following reaction? a. BH3 :THF b. H 2O 2 , NaOH + enantiomer OH

A)

OH

B) OH

+ enantiomer C) Answer: A and C Topic: Reaction Products Section: 8.6, 8.7, 8.8 Difficulty Level: Medium

48) What is the major product for the following reaction? a. BD3 :THF b. CH3 CO2D

+ enantiomer OH

A)

+ enantiomer D

B)

+ enantiomer C)

D

D

27

+ enantiomer D)

D

E)

D

D

Answer: D Topic: Reaction Products Section: 8.6, 8.7, 8.8, 8.10 Difficulty Level: Medium

49) What is the major product for the following reaction? a. BH 3:THF b. CH3CO 2 D + enantiomer

A)

D

OH

+ enantiomer

B) D

+ enantiomer

C) O 2CCH 3

+ enantiomer

D) E) None of these choices. Answer: C Topic: Reaction Products Section: 8.6, 8.7, 8.8, 8.10 Difficulty Level: Medium

50) How many of the products shown below are possible in the following reaction?

28

A) 1 B) 2 C) 4 D) All of them. E) None of them. Answer: C Topic: Reaction Products Section: 8.11 Difficulty Level: Medium

51) What would be the major product of the following reaction? Br2, CCl4 ?

CH3 H

Br

Br

H

H

Br

Br

H

C3H7

I

CH3

CH3

Br

H

H

Br

CH3 H

Br

Br

H

C3H7

C3H7

C3H7

II

III

IV

A) Equal amounts of I and II. B) Equal amounts of II and III. 29

C) Equal amounts of III and IV. D) I and II as major products, III and IV as minor products. E) All of these choices in equal amounts. Answer: A Topic: Reaction Products Section: 8.11 Difficulty Level: Medium

52) What would be the major product of the following reaction? Br2 , CCl4 ? C 2H5

C2H 5

C2 H5

H3C

Br

Br

CH 3 H 3C

Br

H

Br

Br

H

H

C 3H7

I

Br

C2H 5 Br

CH 3

H

Br

C3H 7

C3 H7

C3H 7

II

III

IV

A) Equal amounts of I and II. B) Equal amounts of II and III. C) Equal amounts of III and IV. D) I and II as major products, III and IV as minor products. E) All of these choices in equal amounts. Answer: A Topic: Reaction Products Section: 8.11 Difficulty Level: Medium

53) Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would: A) be a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial. B) be a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial. C) be a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial. D) be a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial. 30

E) be a pair of diastereomers and, in their most stable conformation, one would have the bromines equatorial and axial, and the other would have the bromines equatorial and equatorial. Answer: A Topic: Reaction Products Section: 8.11 Difficulty Level: Medium

54) Compound X has the molecular formula C6H10. X decolorizes bromine in carbon tetrachlorid...