Question 1
Which species acts as the nucleophile in the reaction of 1-butene with bromine water?
A. elemental bromine
B. a hydronium ion
C. a bromide ion
D. water Question 2
Markovnikov's Rule is most useful when predicting the major product formed in which type of
reaction?
A. hydration
B. dehalogenation
C. halogenation
D. dehydrohalogenation
E. hydrogenation
F. hydroxylation
G. dehydration Question 4
Which species acts as the nucleophile in the acid-catalyzed hydration of an alkene?
A. water
B. a hydroxide ion
C. a hydronium ion
D. a carbocation Question 5
Hydrogenation of an alkene, catalyzed by platinum metal, proceeds with __________
stereochemistry and is an example of __________ catalysis. A. anti; homogeneous B. syn; heterogeneous
C. syn; homogeneous
D. anti; heterogeneous Question 6
1,2-Dimethylcyclopentene was treated with MCPBA to give product A. Product A was treated
with aqueous acid to give product B. Which statement is true about product B?
A. Product B is a racemic mixture of the two enantiomers of a cis-glycol.
B. Product B is a racemic mixture of the two enantiomers of a trans-glycol.
C. Product B is a single enantiomer of a trans-glycol.
D. Product B is a single enantiomer of a cis-glycol.
E. Product B is a mixture of the two enantiomers of a cis-glycol, where one enantiomer is
formed in larger amounts than the other enantiomer.
F. Product B is a mixture of the two enantiomers of a trans-glycol, where one enantiomer is
formed in larger amounts than the other enantiomer. Question 8
What is the major product formed in the acid-catalyzed reaction of 2-methyl-2-pentene with
water?
A. 2-methyl-2-pentanol
B. 2-methyl-1-pentanol
C. 2-methylpentane
D. 2-methyl-3-pentanol Question 10
What will be formed when 1,2-dimethylcyclopentene is reacted with hydrogen gas in the
presence of palladium?
A. a mixture of mostly cis-1,2-dimethylcyclopentane and a smaller amount of trans-1,2dimethylcyclopentane
B. a mixture of mostly trans-1,2-dimethylcyclopentane and a smaller amount of cis-1,2dimethylcyclopentane
C. only trans-1,2-dimethylcyclopentane
D. only cis-1,2-dimethylcyclopentane Question 11
When an alkene undergoes oxymercuration-demercuration, the reaction proceeds with
A. Markovnikov orientation and anti addition.
B. Markovnikov orientation and syn addition.
C. anti-Markovnikov orientation and anti addition.
D. anti-Markovnikov orientation and syn addition. Question 12
Which of the following compounds will react most rapidly with HCl?
A. 5-methyl-1-hexene
B. 2-methyl-2-hexene
C. (E)-2-methyl-3-hexene
D. (E)-5-methyl-2-hexene
E. 4-methyl-1-hexene Question 13
Which reagent will convert cyclopentene to a cis-glycol?
A. Hg(OAc)2
B. H2SO4
C. KMnO4
D. H2O2
E. NaBH4 Question 15
The reaction of 1-methylcyclopentene with bromine water proceeds via __________ addition
and gives the __________ product. A. anti; anti-Markovnikov B. anti; Markovnikov
C. syn; anti-Markovnikov
D. syn; Markovnikov Question 16
Which of the following is the best reaction sequence to use if you want to carry out a
Markovnikov addition of water to an alkene with minimal rearrangements?
A. oxymercuration-demercuration
B. water + potassium permanganate
C. water + bromine
D. water + dilute acid
E. water + hydrogen gas + Pt
F. alkoxymercuration-demercuration
G. water + concentrated acid
H. water + MCPBA Question 20
Which of the following is the least likely to react with an alkene?
A. a hydronium ion
B. potassium permanganate
C. sodium methoxide
D. an ethyl radical
E. elemental bromine

 

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