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Solution: What stereoisomers would be obtained from the
Chapter 11, Problem 30P(choose chapter or problem)
Problem 30P
What stereoisomers would be obtained from the reaction of the alkenes in Problem 29 with a peroxyacid followed by reaction with hydroxide ion?
What stereoisomers would be obtained from the reaction of each of the following alkenes with OsO4 followed by aqueous H2O2?
a. trans-2-butene b. cis-2-butene c. cis-2-pentene d. trans-2-pentene
Questions & Answers
QUESTION:
Problem 30P
What stereoisomers would be obtained from the reaction of the alkenes in Problem 29 with a peroxyacid followed by reaction with hydroxide ion?
What stereoisomers would be obtained from the reaction of each of the following alkenes with OsO4 followed by aqueous H2O2?
a. trans-2-butene b. cis-2-butene c. cis-2-pentene d. trans-2-pentene
ANSWER:
Solution 30P
(a)
Treatment of trans-2-butene with peroxy acid gives an epoxide, which is further reacted with nucleophile and forms trans-diol as product. In basic medium opening of epoxide is always at sterically less crowded position. Thus, the reaction is shown as follows:
(b)
Treatment of