There are 8 diastereomers of1,2,3,4,5,6-hexachlorocyclohexane. Draw each in its more stablechair conformation. One isomer loses HCl in an E2 reaction nearly1000x more slowly than the others. Which isomer reacts so slowly,and why?

Falak Kinney

Falak Kinney

Answered question

2021-04-28

There are 8 diastereomers of 1,2,3,4,5,6-hexachlorocyclohexane. Draw each in its more stablechair conformation. One isomer loses HCl in an E2 reaction nearly 1000x more slowly than the others. Which isomer reacts so slowly,and why?

Answer & Explanation

Cullen

Cullen

Skilled2021-04-30Added 89 answers


8 diastereomers of 1,2,3,4,5,6-hexachlorocyclohexane in their morestable chair conformation.
For E2 Elimination in cyclohexane derivatives thestereoelectronic requirement is that the leaving groups should beboth "anti" to each other which is not possible in theβ -isomer.
The β -isomer is the only one that does not have any axialchlorines next to axial hydrogens in either chair conformations andit loses HCl 1000 times more slowly than theother isomers.

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