University of Florida ORGO 215 Package title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 8 Question type: Multiple choice 1)The thermodynamic parameters at 298 K for the following reaction are given below

University of Florida

ORGO 215

Package title: Solomons Test Bank

Course Title: Solomons 11e Chapter Number: 8

Question type: Multiple choice

1)The thermodynamic parameters at 298 K for the following reaction are given below.

gas phase

CH₂=CH₂  +  HCl

CH3CH2Cl                    ?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?

1. Both ?Hº and ?Sº favor product formation.
2. Neither ?Hº nor ?Sº favors product formation.
3. The entropy term is unfavorable but the formation of ethyl chloride is favored.
4. The entropy term is favorable but the formation of ethyl chloride is not favored.
5. The sign of ?Gº indicates that the reaction cannot occur as written.

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?

1. 1. H⁺
   2. NH₃
   3. Ag⁺
   4. Hg²⁺
   5. BF₃

3. Markovnikov addition of HI to 2-methyl-2-butene involves:

1. 1. initial attack by an iodide ion.
   2. initial attack by an iodine atom.
   3. isomerization of 2-iodo-2-methylbutene.
   4. formation of a carbocation at C-2.
   5. formation of carbocation at C-3.

4. What is the major product for the following reaction?

+ enantiomer

2. I

3. I

 I

D)

I

E)

+  enantiomer

+ enantiomer

+ enantiomer

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

              HCl

I                                                      II                                                III

Cl

Cl

IV                                              V

1. 1. I
   2. II
   3. III
   4. IV
   5. V

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

H3C

Cl

I

H3C

H3C

Cl

II

Cl                      Cl

H3C

Cl

III

IV                                              V

1. 1. I
   2. II
   3. III
   4. IV
   5. V

7. How many compounds are possible from the addition of bromine to CH₂=CHCH₂CH₃ (counting stereoisomers separately)?

1. 1. One
   2. Two
   3. Three
   4. Four
   5. Five

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?

1. 1. one optically active fraction only
   2. one optically active fraction and one optically inactive
   3. two optically active fractions
   4. one optically active fraction and two optically inactive
   5. two optically active fractions and one optically inactive

9. What is the major product for the following reaction?

+ enantiomer

A)                             Br

+ enantiomer

+ enantiomer

C)

+ enantiomer

4. Br
5. More than one of these choices.

10. What is the major product for the following reaction?

A)        Cl

3. Cl

4. Cl

Cl

E)

11. What is the major product for the following reaction?

1. 1. Br

Br

B)

+ enantiomer

C)        Br

E) More than one of these choices.

12. Cl

    

    Cl   D H

    

    D   Cl

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

D

I                                                      II

III

D

Cl

IV                                                     V

1. 1. I
   2. II
   3. III
   4. IV

1. 5. V

13. Addition of hydrogen chloride to the following molecule would produce:

Cl

Cl                             Cl

Cl                             Cl

HCl                 ?

Cl                             Cl

Cl

Cl                             Cl                             Cl

I                              II                              III                             IV                            V

1. 1. I and II
   2. II and III
   3. I and IV
   4. V
   5. All of these choices are equally likely to be formed.

14. Consider the addition of HCl to 3-methyl-1-butene. The major product of the reaction would be:

1. 1. 1-Chloro-2-methylbutane
   2. 1-Chloro-3-methylbutane
   3. 2-Chloro-2-methylbutane
   4. 2-Chloro-3-methylbutane
   5. 1-Chloropentane

15. What are possible products for the following reaction?

Br

A)

Br

+ enantiomer

B)

4. Two of these choices.
5. None of these choices.

16. What are the major product(s) formed by treating treating methylcyclopentene with HBr and MeO-OMe?

1. 1. I

1. II
2. III
3. Two of these choices.
4. None of these choices.

17. What is the major product of the following reaction sequence?

1. 
   HBr
2. NaCN, DMSO

1. CN

2. Cl

3. CN

CN     +  enantiomer

CN     +  enantiomer

D)

E) None of these choices.

18. What is the major product of the following reaction sequence?

1. 
   HI
2. t-BuOK, t-BuOH

A)

B)

C)

D)

E) More than one of these choices.

19. What is the major product of the following reaction sequence?

1. 
   HCl
2. t-BuOK, t-BuOH

A)

B)

C)

D)

E)                      O

20. What is the major product of the following reaction sequence?

2. HBr

Br

A)

Br

Br

C)

Br

D)

E) None of these choices.

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:

1. 1. the product is statistically favored.
   2. steric hindrance favors its formation.
   3. it is formed via the more/most stable carbocation.
   4. it is the more/most stable product.
   5. All of these choices are reasons.

22. What is the chief product of the reaction of IBr with 2-methyl-2-pentene?

1. 1. 2-bromo-3-iodo-2-methylpentane
   2. 3-bromo-2-iodo-2-methylpentane

1. 3. 1-bromo-2-iodo-2-methylpentane
   4. 2-bromo-1-iodo-2-methylpentane
   5. All of these choices.

23. Treating 1-methylcyclohexene with H₃O⁺ would yield primarily which of these?

I                                                      II                                                III

HO

OH

IV                                              V

1. 1. I and V
   2. II
   3. III and V
   4. IV
   5. I, III, and V

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

1. 1. I only
   2. II and IV
   3. I and III
   4. IV and V
   5. none of these choices

25. Which product would you expect from the following reaction?

H3O⁺ H2O

OH

I                                                     II OH

OH

IV                                             V

1. 1. I
   2. II
   3. III
   4. IV

1. 5. V

26. What is the chief product of the acid-catalyzed hydration of 2,5-dimethyl-2-hexene?

1. 1. 2,5-dimethyl-1-hexanol
   2. 2,5-dimethyl-2-hexanol
   3. 2,5-dimethyl-3-hexanol
   4. 2,5-dimethyl-2,3-hexanediol
   5. 2,5-dimethyl-3,4-hexanediol

27. Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following?

1. 1. (CH₃)₂C(OH)CH₂CH₃
   2. CH₂OHCH(CH₃)CH₂CH₃
   3. (CH₃)₂CHCHOHCH₃
   4. (CH₃)₂CHCH₂CH₂OH
   5. CH₃CH₂CH(CH₃)CH₂OH

28. When either cis- or trans-2-butene is treated with hydrogen chloride in ethanol, the product mixture that results includes:

1. 1. CH₃CH₂CH₂CH₂Cl
   2. CH₃CH₂CH₂CH₂OCH₂CH₃
   3. CH₃CH₂CH(CH₃)OCH₂CH₃
   4. (CH₃)₃CCl

1. 5. (CH₃)₂CHCH₂OCH₂CH₃

29. Which alkene would you expect to be most reactive toward acid-catalyzed hydration?

1. 1. 1-pentene
   2. trans-2-pentene
   3. cis-2-pentene
   4. 2-methyl-1-butene
   5. All of these would be equally reactive.

30. What is the major product for the following reaction?

1. 
   Hg(OAc)₂, H₂O
2. NaBH₄, NaOH

A)

OH

+ enantiomer

B)

C) OH

E) More than one of these choices.

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)?

HO                                                 HO

+ enantiomer                              + enantiomer

HO

+ enantiomer

I                                                      II                                                    III

OH

HO                                                      HO

+ enantiomer                                meso compound

IV                                                          V

1. 1. I only
   2. II and IV
   3. I and III
   4. IV and V
   5. none of these choices

32. What is the major product for the following reaction?

1. 
   Hg(OAc)₂, H₂O
2. NaBH₄, NaOH

A)                                           O

+ enantiomer

C)

D)

E) None of these choices.

33. What is the major product for the following reaction?

1. 
   Hg(OAc)₂, H₂O
2. NaBH₄, NaOH

+ enantiomer

+ enantiomer

C)

E)

+   enantiomer

+ enantiomer

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

A)

+ enantiomer

B)                      O

OH

C)

O

D)

E) None of these choices.

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

A)               O

O

HO                           + CO₂

D)

HO

E)

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

OCH3

C)

OH

D)

E) More than one of these choices.

37. What is the major product of the following reaction sequence?

2a. Hg(OAc)₂, H₂O

2b. NaBH₄, NaOH

1. OH

2. OH

3. O

HO

D)

HO

E)

38. What is the major product of the following reaction sequence?

Cl                               2a. BH₃:THF 2b. H₂O₂, NaOH

1. 1. HO

1. 2. OH

1. 3. OH

+ enantiomer

+ enantiomer

D)

E) An equal mixture of two of these choices.

39. What is the major product of the following reaction sequence?

2a. BH₃:THF

2b. H₂O₂, NaOH

H

B)               O

D)

E)                            OH

40. What is the major product of the following reaction sequence?

2a. O₃, CH₂Cl₂, -78 ^oC

2b. Me₂S

O

A)

CHO

B)

OH  OH

C)

D)

O

CHO

+ enantiomer

E) More than one of these choices.

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

1. O3
2. Me2S

Camphene

CO2

I                                                                  II                                            III

IV

1. 1. I, II, V
   2. II, III
   3. I, V
   4. II, V
   5. III, IV

CH2O V

42. What is the major product of the following reaction sequence?

2a. O₃, CH₂Cl₂, -78 ^oC

2b. Me₂S

O

1. O

OH

2. OH

O

3. O

CHO

4. CHO
5. None of these choices.

43. What is the major product for the following reaction?

1. 
   BH₃:THF
2. H₂O₂, NaOH

OH

+ enantiomer

A)

B)

3. OH

H

4. O

+ HCHO

5. OH

44. What is the major product for the following reaction?

HO

A)

O

B)                             OH

C)

OH

D)

1. BH₃:THF

2. H₂O₂, NaOH

+  CO₂

+ enantiomer

E)

OH       + enantiomer

OH

45. What is the major product for the following reaction?

1. 
   BH₃:THF
2. H₂O₂, NaOH

HO

+ enantiomer

B)

HO

+ enantiomer

C)

OH

+ enantiomer

D)

E) More than one of these choices.

46. What is the major product for the following reaction?

1. 
   BH₃:THF
2. H₂O₂, NaOH

OH

A)        OH

O

H

B)

3. OH

4. OH

5. OH

+ enantiomer

O

+  enantiomer

+ enantiomer

47. What is the major product for the following reaction?

1. 
   BH₃:THF
2. H₂O₂, NaOH

A)                             OH

C)

+ enantiomer

OH

+ enantiomer

4. All of these choices are major products.
5. A mixture of two of these choices.

48. What is the major product for the following reaction?

1. 
   BD₃:THF
2. CH3CO2D

3. D

4. D

5. D

+ enantiomer

+ enantiomer

D

49. What is the major product for the following reaction?

1. 
   BH₃:THF
2. CH3CO2D

A)

OH        + enantiomer

B)

D       + enantiomer

C)

O2CCH3

D)

+ enantiomer

E) None of these choices.

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

1. 1. 1
   2. 2
   3. 4
   4. All of them.
   5. None of them.

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

Br2, CCl4

?

CH₃

H           Br

H           Br

C₃H₇

I

CH₃

Br             H

Br             H

C₃H₇

II

CH₃

H           Br

Br             H

C₃H₇

III

CH₃

Br             H

H           Br

C₃H₇

IV

1. Equal amounts of I and II.
2. Equal amounts of II and III.

3. Equal amounts of III and IV.
4. I and II as major products, III and IV as minor products.
5. All of these choices in equal amounts.

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

Br2, CCl4

?

H3C

H

C2H5

Br Br

C3H7

C2H5

Br            CH3

Br             H

C3H7

H3C

Br

C2H5

Br H

C3H7

C2H5

C3H7

I                                II                            III                              IV

1. 1. Equal amounts of I and II.
   2. Equal amounts of II and III.
   3. Equal amounts of III and IV.
   4. I and II as major products, III and IV as minor products.
   5. All of these choices in equal amounts.

53. Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would:

1. 1. be a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial.
   2. be a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial.
   3. be a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial.
   4. be a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial.

1. 5. 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.

54. Compound X has the molecular formula C₆H₁₀. X decolorizes bromine in carbon tetrachloride. X also shows IR absorption at about 3300 cm^-1. When treated with excess hydrogen and a nickel catalyst, X yields 2-methylpentane. The most likely structure for X is:

A)

B)

C)

D)

E)

55. What is the major product of the following reaction sequence?

1. 
   Br₂, CCl₄

2a. NaNH2 (excess), NH3 2b. H3O+

A)

B)

C)

4. Br
5. More than one of these choices.

56. What reagent sequence might accomplish the following transformation?

1. 1. 1) Br₂, 2)excess KOH, 3)H₃O⁺
   2. 1) HBr, 2)excess KOH, 3) H₃O⁺
   3. 1) HBr, 2)excess NaNH₂, 3) H₃O⁺
   4. 1) Br₂, 2) excess NaNH₂, 3) H₃O⁺
   5. none of these choices

57. A synthetic strategy for converting trans-2-butene into pure cis-2-butene would consist of which of the following?

1. 1. Reaction with H₂, Ni₂B (P-2)
   2. Reaction with i) Br₂, CCl₄; ii) 2 NaNH₂, NH₃(l); iii) Na, NH₃ (l)
   3. Reaction with H₃O⁺, heat
   4. Reaction with i) Br₂, CCl₄; ii) 2 NaNH₂, NH₃(l); iii) H₂, Ni₂B (P-2)
   5. None of these will successfully effect the desired transformation.

58. What is the major product of the following reaction sequence?

2. Br₂, CCl₄

Br

A)                      Br

B)

Br

D)

+ enantiomer

+ enantiomer

+  enantiomer

+ enantiomer

E)

59. What is the major product of the following reaction sequence?

1. 
   H₂, Lindlars catalyst
2. Br₂, CCl₄

+ enantiomer

A)

B)

Br

D)

E)

+ enantiomer

+  enantiomer

+ enantiomer

60. Which reaction sequence would convert cis-2-butene to trans-2-butene?

1. 1. Br₂/CCl₄; then 2 NaNH₂; then H₂/Ni₂B(P-2)
   2. Br₂/CCl₄; then 2 NaNH₂; then Li/liq. NH₃
   3. H₃O⁺, heat; then cold dilute KMnO₄
   4. HBr; then NaNH₂; then H₂, Pt
   5. None of these choices.

61. The reaction of BrCl (bromine monochloride) with 1-methylcyclopentene will produce which of the following as the predominant product:

CH3                       CH3

CH3

CH3

CH2Cl

Br                           Cl                              Br                            Cl                             Br Cl  Br                                 Cl                          Br

+                              +                              +                             +                                +

enantiomer

enantiomer

enantiomer

enantiomer

enantiomer

I                              II                              III                           IV                               V

1. 1. I
   2. II
   3. III
   4. IV
   5. V

62. Which of these compounds will react with cold concd. H₂SO₄, as well as Br₂ in CCl₄?

1. 1. CH₃CH₂CH=CHCH₃
   2. CH₃CH₂CH₂CH=CH₂
   3. CH₃CH₂C?CCH₃
   4. (CH₃)₂CHC?CH
   5. All of these choices.

63. Which reaction is NOT stereospecific?

trans-2-Butene

Br₂/CCl₄

cis-2-Pentene

Br₂/H₂O

I                                                                                                              II

1-Methylcyclohexene         D2/Pd III

2-Methyl-2-heptene

IV

dil KMnO₄ 5oC

trans-2-Hexene V

HBr

1. I
2. II
3. III
4. IV
5. V

64. What is the major product for the following reaction?

1. Br

Br     + enantiomer

2. Br

+ enantiomer

Br

3. Br

4. Br
5. More than one of these choices.

65. What is the major product for the following reaction?

Cl

Cl

C)

Cl

D)

+ enantiomer

+ enantiomer

+ enantiomer

E) More than one of these choices.

66. What are the major product(s) formed by treating 1,2-dimethyl cyclopentene with Br₂?

B

I                                                           II                                                                III

B

IV                                                               V

1. 1. I,II
   2. II, III
   3. IV, V
   4. I, III
   5. None of these choices.

67. Reaction of trans-2-hexene with a solution of Br₂ in CCl₄ produces:

Br     

Br

H

Br          H        

H

Br

H

Br

I                                               II                                                 III

Br                                                               H             

Br                              H               H

H                                     Br       Br

IV                                                V

1. 1. I and II
   2. II and V
   3. III and IV
   4. IV and V
   5. V

68. The reaction of Br₂/CCl₄ to cyclohexene would produce the compound(s) represented by structure(s):

H                                                  Br                           Br

I                                                   II                                                 III

1. 1. I alone
   2. II alone
   3. II and III
   4. III alone
   5. I, II, and II

69. Which of these is not a possible product when cyclopentene reacts with an aqueous solution of bromine?

Br                OH

OH                          Br

Br                     Br                OH Br                                Br                            OH

I                              II                            III                            IV                            V

1. 1. I
   2. II
   3. III
   4. IV
   5. V

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

Br₂, H₂O                     ?

71. What is the major product for the following reaction?

1. Cl

   OH

OH

2. Cl

   Cl

3. OH

OH

Cl

+ enantiomer

D)

E) None of these choices.

72. Which of these compounds belongs to the class of substances commonly known as "halohydrins"?

1. 1. BrCH₂CH₂Cl
   2. ClCH₂CO₂H
   3. ICH₂CH₂OH
   4. FCH₂CH₂NH₂
   5. HOCH₂COCl

73. What is the major product for the following reaction?

HO

1. Br

HO

2. OH

Br

3. OH

HO

4. Br

+ enantiomer

+   enantiomer

+   enantiomer

+   enantiomer

+  enantiomer

Br

5. OH

74. What is the major product for the following reaction?

1. Br

2. Br

OH

OCH₃

Br

+ enantiomer

+ enantiomer

+ enantiomer

3. Br

   H₃CO

D)

OCH3

+ enantiomer

E) More than one of these choices.

75. What is the major product of the following reaction sequence?

1. 
   Br₂, H₂O
2. NaH, THF

O- Na+

D)

+ enantiomer

+ enantiomer

+ enantiomer

+ enantiomer

E) None of these choices.

76. Which of these compounds is not formed when gaseous ethene is bubbled into an aqueous solution of bromine, sodium chloride and sodium nitrate?

1. 1. BrCH₂CH₂Br
   2. BrCH₂CH₂Cl
   3. BrCH₂CH₂OH
   4. ClCH₂CH₂OH
   5. BrCH₂CH₂ONO₂

77. What is the major product for the following reaction?

t-BuOK

Cl

Cl

+ enantiomer

A)

B)

Cl

C)                              Cl

Cl

Cl

D)

+ enantiomer

+ enantiomer

E) More than one of these choices.

78. What is the major product of the following reaction sequence?

1. 
   Li, CH₃CH₂NH₂
2. t-BuOK, CHCl₃

Cl      Cl

+ enantiomer

A)

+ enantiomer

C)

Cl       Cl

+ enantiomer

D)

E) More than one of these choices.

79. What is the major product for the following reaction?

Zn(Cu)

I      I

A)

B)

I

C)

D)

E) More than one of these choices.

80. What product would result from the following reaction?

1. 1. I
   2. II
   3. III
   4. IV
   5. V

81. Which reagent(s) given below could be used to synthesize cis-1,2-cycloheptanediol from cycloheptene?

1. 1. KMnO₄, OH^?, 5^oC
   2. KMnO₄, H₃O⁺, 75^oC
   3. H₂SO₄, heat
   4. All of these choices.
   5. None of these choices.

82. Which set of reagents might be used to convert bromocyclohexane into cis-1,2- cyclohexanediol?

1. 1. 1) Potassium tert-butoxide, 2) H₃O+

1. 2. 1) Potassium tert-butoxide, 2) OsO₄, pyridine then NaHSO₄(aq)
   3. 1) KOH, 2) KMnO₄, H+, heating
   4. 1) NaOH, 2) H₃O+, heating
   5. none of these choices

83. Cyclohexene is treated with cold dilute alkaline KMnO₄. Assuming syn addition, the spatial arrangement of the two hydroxyl groups in the product would be:

1. 1. equatorial-axial
   2. axial-axial
   3. equatorial-equatorial
   4. coplanar
   5. Trans

84. Hydroxylation of cis-2-pentene with cold alkaline KMnO₄ yields

CH₃

H           OH

H           OH

C₂H₅

CH₃

HO           H

HO           H

C₂H₅

CH₃

H           OH

HO           H

C₂H₅

CH₃

HO           H

H           OH

C₂H₅

I                               II                            III                             IV

1. Equal amounts of I and II.
2. Equal amounts of II and III.
3. Equal amounts of III and IV.
4. I and II as major products, III and IV as minor products.
5. All of these choices in equal amounts.

85. 3,3-dimethylcyclohexene is subjected to reaction with cold, dilute KMnO₄, to give 3,3- dimethyl-1,2-cyclohexanediol. In the most stable conformation of the product, the hydroxyl groups would be:

1. 1. both axial
   2. both equatorial
   3. axial-equatorial
   4. coplanar
   5. None of these choices.

86. An optically active compound, Y, with the molecular formula C₇H₁₂ gives a positive test with cold dilute KMnO₄ and shows IR absorption at about 3300 cm^-1. On catalytic hydrogenation, Y yields Z(C₇H₁₆) and Z is also optically active. Which is a possible structure for Y?

1. 1. CH₃CH₂CH₂CH₂CH₂C?CH
   2. (CH₃)₂CHCH₂CH₂C?CH
   3. CH₃CH₂CH(CH₃)CH₂C?CH
   4. CH₃CH₂CH(CH₃)C?CCH₃
   5. CH₂=CHCH(CH₃)CH₂CH=CH₂

87. An optically active compound, A, with the molecular formula C₇H₁₂ reacts with cold dilute KMnO₄ and gives IR absorption at about 3300 cm^-1. On catalytic hydrogenation, A is converted to B (C₇H₁₆) and B is also optically active.  Which is a possible structure for A?

I                                                      II                                                III

IV                                              V

1. 1. I
   2. II
   3. III
   4. IV
   5. V

88. Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?

A)

B)

C)

D)

E)

89. What is the major product of the following reaction sequence?

1. NaOEt, HOEt, heat

Cl

2. KMnO₄, NaOH, cold

O

+

1. O                                             OH

OH

2. O

+   CO₂

3. OH

OH      +   enantiomer

4. OH

+ enantiomer

OH

5. More than one of these choices.

90. What is the final product of the following synthesis?

2-Butyne

H2

Ni₂B (P-2)

C₄H₈

1. OsO4

2. CH3

   NaHSO₄

Final Product

CH₃

HO             H

CH₃

HO             H

H             OH

H             H

CH₃

HO             H

CH₃

H             OH

CH₃

HO             H

CH₃

I                                      II                                     III                                     IV

1. I

2. II
3. III
4. IV
5. An equimolar mixture of III and IV.

91. Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between pure 1-pentene and pure pentane?

1. 1. Bromine in carbon tetrachloride
   2. Dilute aqueous potassium permanganate
   3. Concentrated sulfuric acid
   4. All of these choices.
   5. Bromine in carbon tetrachloride and dilute aqueous potassium permanganate only

92. Which reagent or test could be used to distinguish between 2-methyl-2-pentene and 2- methylpentane?

1. 1. Br₂/CCl₄
   2. KMnO₄, OH^?
   3. Concd. H₂SO₄
   4. Two of these choices.
   5. All of these choices.

93. Which reaction would yield a meso compound?

1. 1. cis-2-Butene

Br₂/CCl₄

1. 2. cis-2-Butene                H2/Pd

cis-2-Butene               i) OsO4

C)

trans-2-Butene

D)

ii) NaHSO₃

dil KMnO₄

5^oC

E) None of these choices.

94. Which reaction would give a meso compound as the product?

1. 1. Cyclopentene + Br₂/CCl₄
   2. Cyclopentene + OsO₄, then NaHSO₃
   3. Cyclopentene + H₃O⁺
   4. Cyclopentene + Cl₂, H₂O
   5. More than one of these choices.

95. A pair of enantiomers results from which of these reactions?

1. 1. cyclopentene + cold, dil. KMnO₄ ?????
   2. trans-2-butene + Br₂ ?????
   3. 1-pentene + HCl ?????
   4. cis-2-butene + D₂/Pt ?????
   5. cyclobutene + OsO₄, then Na₂SO₃          ?????

96. Which of the following reactions would yield the final product as a racemic form?

1. 1. Cyclohexene + Br₂, H₂O
   2. Cyclohexene + cold, dilute KMnO₄ and OH^-
   3. Cyclohexene + HCl
   4. Cyclohexene + OsO₄, then NaHSO₃
   5. Cyclohexene + D₂/Pt

97. Which reaction is regioselective?

Cl

1. ICl                              I

2. Br2

               Br

Br

IV

OH

  KMnO₄

OH

H

D2/Ni                              D

D

H

1. I
2. II
3. III
4. IV
5. None of these choices.

98. Which reaction would yield a racemic product?

1. 1. Cyclopentene + D₂/Pt ?????
   2. Cyclopentene + OsO₄, then Na₂SO₃ ?????
   3. Cyclopentene + Br₂/H₂O ?????
   4. Cyclopentene + cold, dilute KMnO₄ ?????
   5. Cyclopentene + dilute H₂SO₄ ?????

99. Which reaction of an alkene proceeds with anti addition?

1. 1. Hydroboration/oxidation
   2. Bromination
   3. Oxidation with cold KMnO₄
   4. Hydrogenation
   5. Oxymercuration-demercuration

100. What is the major product of the following reaction?

1. 
   OsO₄, pyridine
2. H₂O, NaHSO₃

OH

B)

+ enantiomer

+ enantiomer