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  4. 2-Phenylethylbromide when heated with NaOEt, elimination takes place. No deuterium exchange takes place when the reaction is carried out in C2H5OD solvent. The mechanism will be

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Q. $2$-Phenylethylbromide when heated with $NaOEt$, elimination takes place. No deuterium exchange takes place when the reaction is carried out in $C_2H_5OD$ solvent. The mechanism will be

AIIMSAIIMS 2009Organic Chemistry – Some Basic Principles and Techniques

Solution:

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It is a primary bromide. So it will undergo elimination either by $E2$ or $E1cB$. Since there is no deuterium exchange in $C _{2} H _{5} OD$ solvent, $C-H$ bond is not broken to form carbanion. Hence the actual mechanism is $E2$ only.

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