Question

24) 1) O? 2) (CH?)?S 25) 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 OsO? E) none of the above 26) Provide a detailed, step-by-step mechanism for the reaction shown below. HO Br? + HBr 27) Provide a detailed, step-by-step mechanism for the reaction shown below. O H?O? HO 28) Provide the reagents necessary to complete the following transformation. The synthesis may involve more than one step. Br OH ? OH 29) Provide the reagents necessary to complete the following transformation. The synthesis may involve more than one step. Br ? OH + enantiomer OH 30) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol. The synthesis may involve more than one step. 31) Both \textit{(E)}- and \textit{(Z)}-hex-3-ene are subjected to a hydroboration-oxidation sequence. How are the products from these two reactions related to each other? A) The \textit{(E)}- and \textit{(Z)}-isomers generate the same products but in differing amounts. B) The \textit{(E)}- and \textit{(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 not structurally related.

          24)
1) O?
2) (CH?)?S
25) 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 OsO?
E) none of the above
26) Provide a detailed, step-by-step mechanism for the reaction shown below.
HO
Br?
+ HBr
27) Provide a detailed, step-by-step mechanism for the reaction shown below.
O
H?O?
HO
28) Provide the reagents necessary to complete the following transformation. The synthesis may involve
more than one step.
Br
OH
?
OH
29) Provide the reagents necessary to complete the following transformation. The synthesis may involve
more than one step.
Br
?
OH
+ enantiomer
OH
30) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol. The synthesis
may involve more than one step.
31) Both \textit{(E)}- and \textit{(Z)}-hex-3-ene are subjected to a hydroboration-oxidation sequence. How are the
products from these two reactions related to each other?
A) The \textit{(E)}- and \textit{(Z)}-isomers generate the same products but in differing amounts.
B) The \textit{(E)}- and \textit{(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 not structurally related.

24)
1) O?
2) (CH?)?S
25) 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 OsO?
E) none of the above
26) Provide a detailed, step-by-step mechanism for the reaction shown below.
HO
Br?
+ HBr
27) Provide a detailed, step-by-step mechanism for the reaction shown below.
O
H?O?
HO
28) Provide the reagents necessary to complete the following transformation. The synthesis may involve
more than one step.
Br
OH
?
OH
29) Provide the reagents necessary to complete the following transformation. The synthesis may involve
more than one step.
Br
?
OH
+ enantiomer
OH
30) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-methyl-2-butanol. The synthesis
may involve more than one step.
31) Both (E)- and (Z)-hex-3-ene are 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 (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 not structurally related.

Added by Michelle K.

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