Solution

LiAlH4 reduces the carbonyl to an alcohol, H2SO4 dehydrates it, HBr adds, and Wurtz-Fittig coupling gives D.

$CH_3-CHO\xrightarrow{LiAlH_4}CH_3CH_2OH\xrightarrow{H_2SO_4}CH_2=CH_2\xrightarrow{HBr}CH_3CH_2Br$ (C) Wurtz-Fittig reaction gives (D). [add image] $LiAlH_4$ used for reduction of carbonyl group into alcohol and $H_2SO_4$ used for dehydration of alcohol.

Concept multi-step reaction sequence

Aldehydes, Ketones and Carboxylic Acids in past papers

91 questions from this chapter have appeared across 27 exam years.