Organic Chemistry Chapter 8

34) 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 tre

B yields a meso epoxide

46) Both (E)- and (Z)-hex-3-ene can be subjected to a hydroboration-oxidation sequence. 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 (

B The (E)- and (Z)-isomers generate the same products in exactly the same amounts

47) 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)

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

50) 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-dibr

A) a meso dibromide

57) 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-demercuratio

C) oxymercuration-demercuration

59) 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

60) Which of the following additions to alkenes occur(s) specifically in an syn fashion?
A) dihydroxylation using OsO4, H2O2
B) addition of H2
C) hydroboration
D) addition of HCl
E) A, B, and C

E) A, B, and C

61) 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

63) 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

B) carbocation

65) 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

B) Markovnikov addition of H2O wherein skeletal rearrangement is prevented

65) 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

B) Markovnikov addition of H2O wherein skeletal rearrangement is prevented

66) 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

67) Which of the following compounds is (are) appropriate to promote the cationic polymerization of isobutylene?
A) H2SO4
B) BF3
C) ROOR
D) NaOH
E) both H2SO4 and BF3

E) both H2SO4 and BF3

91) Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?
A)
B)
C)
D)
E) both Band D

B)

92) 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) compo

E) none of the above

Diff: 2
93) 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

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

95) 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 NaB

E) both A and B

96) An unknown compound with empirical formula C3H5 was treated with Br2/CCl4. The bromine solution went from orangish/red to clear immediately at room temperature. Upon treatment with O3 followed by work-up with dimethylsulfide the following products wer

A)