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Question

Predict the major product of the following reaction:

And select the major product:

A
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B
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C
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D
None of the above
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Solution

The correct option is C
This is clearly an intermediate step for Hofmann elimination. The substrate – which is a salt – contains the base OH as a part of it and the heat given according to the reaction points towards β-elimination. The only question, which β-hydrogen will be abstracted by the hydroxide base?
The Hofmann product, unlike the Zaitsev product, is one that is obtained based on the abstraction of the β-hydrogen that is the least hindered. So the hydrogen attached to the homocyclic (cyclohexane) carbon is not abstracted. Any one of the 6 equivalent β-hydrogen atoms are removed from the two equivalent (in terms of abstraction of β-hydrogen) methyl groups attached to the α-carbon.

The above product is the overwhelming major product! The following is not formed.

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