Wednesday, March 1, 2017

organic chemistry - Elimination of HCl from isomeric chlorocyclohexadienes



Which of these is most easily dehydrohalogenated?


Chlorocyclohexadienes


a. 5-Chlorocyclohexa-1,3-diene (1)
b. 3-Chlorocyclohexa-1,4-diene (2)

c. 1-Chlorocyclohexa-1,4-diene (3)
d. Both 1 and 3



I encountered this question a while ago. The given answer is option (b) (compound 2). But the dehydrohalogenation of compound 1 produces benzene which has high heat of formation. So why isn't that the answer?




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