Which of the following is not formed by the addition of 1 mole of HCl to 2-methyl-1,3 cyclohexadiene?

Options

A. 3-chloro-1-methylcyclohexene
B. 1-chloro-6-methylcylohexene
C. 3-chloro-3-methylcyclohexene
D. 6-chloro-l-methylcyclohexene

Answer

B

Explanation

1-Chloro-6-methylcylohexene is not a product obtained from the addition of HCl to 2-methyl-1,3-cyclohexadiene. To answer this question, draw the two resonance structures of both of the allylic carbocations formed by protonation of the double bonds of the starting material (i.e., a total of four resonance structures). Nucleophilic addition of chloride to these carbocations will give the products of this reaction, which will all be allylic chlorides. 1-Chloro-6-methylcylohexene is 6 not an allylic chloride