Consider the 2 isomers of 3,4-dimcthyl-3-hexane to the right: Which isomer will

Question

Consider the 2 isomers of 3,4-dimcthyl-3-hexane to the right: Which isomer will give achiral when it reacts with OsO_4? Which isomer will give achiral 3,4-dibromo-3,4-dimethylhexanc when it reacts with bromine? The E and Z isomers will both give the same mixture of stereoisomers upon addition of HBr. How many stereoisomers will be formed? How many stercoisomcric alcohols will be formed when the Z isomer is reacted with borane in ether, followed by workup with hydrogen peroxide plus base? How many stereoisomeric alcohols will be formed when the E isomer is reacted with borane in ether, followed by workup with hydrogen peroxide plus base? Will the stereoisomers in part D be enantiomers or diastereomers? Will these isomers have different boiling points? Consider one isomer from part D and one from part E. Will these two isomers be enantiomers or diastereomers?

Explanation / Answer

A. Of the two isomers, Z would yield achiral (meso) product upon reaction with OsO4. E would give a dl pair.

B. Of the two isomers, E would yield an achiral (meso) product upon reaction with Br2. Z would yield a dl pair.

C. Four stereoisomers are possible, two as meso and two as dl pair.

D. Two stereoisomers are possible as dl pair (RR and SS)

E. One meso isomer is formed in this case (pair of enantiomers as RS and SR)

F. The stereisomers will be enantiomers is part D. Both the isomers will have the same boiling points.

G. The isomers from part D and part E would be diastereomers of each other.

F.

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