Chapter 8 TB

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40) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

1) Provide the structure of the major organic product of the reaction below.

2) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

3) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

4) HBr can be added to an alkene in the presence of peroxides (ROOR). What function does the peroxide serve in this reaction?
A) nucleophile
B) electrophile
C) radical chain initiator
D) acid catalyst
E) solvent

C) radical chain initiator

5) Predict the major product of the following reaction.

B

6) Name the major product which results when HBr is added to 3-ethyl-3-hexene.

3-bromo-3-ethylhexane

7) Provide the structure of the major organic product of the reaction below.

8) Provide the major organic product of the reaction below.

9) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

10) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

11) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

12) Based on the relative stabilities of the intermediates involved, explain the basis for Markovinkov’s rule in the addition of hydrogen halides to alkenes.

The rate-determining step in this reaction is the production of a carbocation intermediate. Since this step is endothermic, Hammond’s postulate allows one to gauge the relative stabilities of the transition states by comparing the relative stabilities of the carbocation intermediates. The reaction pathway which produces the more substituted carbocation will thus occur more rapidly.

13) Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

14) When propylene reacts with hydrogen bromide in the presence of a peroxide initiator, which of the following structures are formed during the mechanism?

B

15) Using any alkene as your starting material, how could you make the alkyl halide shown?

16) Draw the major regioisomeric product generated in the reaction below.

18) Draw a full and complete mechanism to account for the formation of the product in the reaction shown below.

17) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

19) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

20) Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.

The reaction proceeds via the addition of Br∙ to the alkene. Two competing pathways are possible, but the transition state leading to the more substituted alkyl radical is lower in energy. This process ultimately makes the addition anti-Markovnikov in nature.

21) When 3,6-dimethylcyclohexene is reacted with dry gaseous HBr, one of the products is 1-bromo-1,4-dimethylcyclohexane. Provide a detailed step-by-step mechanism to explain the formation of this product.

f

22) Which radical is an intermediate in the following reaction?

Answer: A

23) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

24) The mechanism for the acid-catalyzed hydration of alkenes is simply the reverse of the mechanism by which alcohols are dehydrated using concentrated acid. This is an illustration of the principle of ________.

microscopic reversibility

25) Acid catalyzed hydration (H2SO4/water/△) of an unknown compound (A) with a chemical formula C6H12, yielded a racemic mixture of product C6H13OH. Which, if any, of the following compounds is/are possible structures for the initial compound (A)?

A) compound 1 only
B) compounds 2 and 3
C) compound 2 only
D) compounds 1 and 3
E) none of the above

Answer: Ey

26) Name the major alcohol product which results when 3,3-dimethylbut-1-ene is treated with dilute acid.

2,3-dimethyl-2-butanol

27) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

28) What is the major product of the following reaction?

Answer: D

29) Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

30) Which of the following intermediates is thought to occur in the mechanism by which alkenes are hydrated in the presence of acid?
A) carbanion
B) carbocation
C) free radical
D) carbene
E) alkyne

Answer: B

31) Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

32) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-
B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O

Answer: B

33) Provide the structure of the major organic product of the reaction below.

34) Treatment of an alkene with an alcohol in the presence of an acid catalyst produces an ether as the major organic product. Provide a mechanism that shown how this product is formed.

35) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

36) Which one of these alkene would be likely to experience a carbocation rearrangement when treated with aqueous acid?

Answer: B

37) Provide the reagents necessary to complete the following transformation.

1) Br2, hν 2) H2O, Δ

38) Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

A) water + dilute acid
B) water + concentrated acid
C) oxymercuration-demercuration
D) hydroboration-oxidation
E) none of the above

C) oxymercuration-demercuration

39) What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration sequence?
A) Markovnikov addition of H2O wherein skeletal rearrangement is promoted
B) Markovnikov addition of H2O wherein skeletal rearrangement is prevented
C) anti-Markovnikov addition of H2O wherein skeletal rearrangement is promoted
D) anti-Markovnikov addition of H2O wherein skeletal rearrangement is prevented
E) syn-hydroxylation

B) Markovnikov addition of H2O wherein skeletal rearrangement is prevented

41) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

42) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

43) Which one of these alkene would be likely to experience a carbocation rearrangement when treated with Hg(OAc)2 in water, followed by reaction with sodium borohydride?

D) None of these would undergo a rearrangement.

44) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

45) When an alkene is subjected to treatment with Hg(OAc)2 in alcohol followed by reaction with NaBH4, what new class of compound is formed?
A) ether
B) epoxide
C) alkane
D) syn diol
E) alkyne

A) ether

46) Provide the structure of the major organic product of the reaction below.

47) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol.

1) conc. H2SO4 2) H3O+

48) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

49) Treatment of 2-methylpropene with which of the following reaction conditions results in an anti-Markovnikov addition product?
A) dry gaseous HBr with peroxides present
B) BH3-THF, followed by alkaline H2O2
C) aqueous Hg(OAc)2, followed by alkaline NaBH4
D) dilute H2SO4 and heat
E) both A and B

E) both A and B

50) How many moles of BH3 need to be added to completely react with 1 mole of hex-1-ene?
A) 1 mole of BH3
B) 3 mole of BH3
C) 1/3 mole of BH3
D) 1/2 mole of BH3

C) 1/3 mole of BH3

51) Provide the structure of the major organic product of the reaction below.

52) Provide the structure of the major organic product of the reaction below.

53) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

54) Complete the following reaction by filling in the appropriate reagents.

55) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-
B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O

A) 1. BH3∙THF 2. H2O2, HO-

56) Provide the structure of the major organic product of the reaction below.

57) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

58) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

59) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

$

60) Use a transition state to explain the regiochemistry of the reaction below. Make sure to include correct partial charges.

The boron adds to the less sterically hindered carbon. The partial positive charge ends up on the more substituted carbon.

61) Which of the following additions to alkenes occur(s) specifically in an anti fashion?
A) hydroboration-oxidation
B) addition of Br2
C) addition of H2
D) addition of H2O in dilute acid
E) both A and B

B) addition of Br2

62) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

63) Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

64) Addition of Br2 to (E)-hex-3-ene produces ________.
A) a meso dibromide
B) a mixture of enantiomeric dibromides which is optically active
C) a mixture of enantiomeric dibromides which is optically inactive
D) (Z)-3,4-dibromo-3-hexene
E) (E)-3,4-dibromo-3-hexene

A) a meso dibromide

65) Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?

Answer: B

66) Provide the major organic product of the reaction below.

67) Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

f

68) Provide a detailed, step-by-step mechanism for the reaction shown below.

69) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

70) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

71) Consider how the I—Cl bond is polarized and predict the product which results when this mixed halogen adds to 1-methylcyclohexene.

72) Provide the structure of the major organic product of the reaction below.

73) Predict the product of the following reaction. Include any relevant stereochemistry.

ff

74) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

75) Using any alkene as a starting material, how would you make the compound shown below?

76) Draw a full and complete mechanism for the following reaction.

77) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

78) Both (E)- and (Z)-hex-3-ene can be treated with D2 in the presence of a platinum catalyst. How are the products from these two reactions related to each other?
A) The (E)- and (Z)-isomers generate the same products but in differing amounts.
B) The (E)- and (Z)-isomers generate the same products in exactly the same amounts.
C) The products of the two isomers are related as constitutional isomers.
D) The products of the two isomers are related as diastereomers.
E) The products of the two isomers are related as enantiomers.

D) The products of the two isomers are related as diastereomers.

79) ________ is the use of an optically active reagent or catalyst to convert an optically inactive starting material into an optically active product.
A) Asymmetric induction
B) Racemization
C) Optical reduction
D) Meso effection
E) Chiralization

A) Asymmetric induction

80) Humulene is a monocyclic terpene constituent of carnations. When 0.25 mol of humulene is hydrogenated in the presence of platinum catalyst, 0.75 mol of H2 reacts with the humulene to produce a monocyclic hydrocarbon of formula C15H30. What is the molecular formula of humulene?

C15H24

81) Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

82) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

83) One method of making a carbene uses diazomethane, CH2N2, which is zwitterionic. Draw the Lewis Structure of diazomethane and any additional resonance structures of this compound.

84) Complete the following reaction by filling in the necessary reagents.

85) Provide the reagents necessary to complete the following transformation.

1) Br2, hν 2) NaOCH3, CH3OH 3) CH2I2, Zn(Cu)

86) Name the compound PhCO3H and give its most common use as a reagent

peroxybenzoic acid; an oxidizing agent which converts alkenes to epoxides

87) Provide the major organic product of the reaction below.

88) Draw a mechanism that shows how the product is formed.

89) Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.s

90) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-
B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O

D) CH3CO3H

91) Treatment of cyclopentene with peroxybenzoic acid ________.
A) results in oxidative cleavage of the ring to produce an acyclic compound
B) yields a meso epoxide
C) yields an equimolar mixture of enantiomeric epoxides
D) gives the same product as treatment of cyclopentene with OsO4
E) none of the above

B) yields a meso epoxide

92) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.c

93) Which of the following steps would successfully complete the following reaction?

A) I only

94) Provide the major organic product of the reaction below.

95) Provide the reagents necessary to complete the following transformation.

A) 1. BH3∙THF 2. H2O2, HO-
B) H2O, H2SO4
C) OsO4, H2O2
D) CH3CO3H
E) 1. CH3CO3H 2. H+, H2O

E) 1. CH3CO3H 2. H+, H2O

96) Provide the structure of the major organic product of the reaction below.

97) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

98) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

99) Provide a detailed, step-by-step mechanism for the reaction shown below.r

100) A reaction of an unknown alkene with MCPBA in dichloromethane followed by work-up with H2O/H+ yielded, as the major product, a racemic mixture of (2S,3S) and (2R,3R)-3-methylpentan-2,3-diol. What is the specific structure of the alkene used in the reaction?
A) (Z)-3-methylpent-2-ene
B) (E)-3-methylpent- 2-ene
C) 2-methylpent-2-ene
D) 2,3-dimethylbut-2-ene
E) none of the above

A) (Z)-3-methylpent-2-ene

101) Provide the reagents necessary to complete the following transformation.

1) NaOCH3, CH3OH 2) MCPBA or CH3CO3H 3) H3O+ or -OH

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