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Chapter 15: Q59. (page 570)

Question: Devise a synthesis of CH2 CH2CH2CH2Br from HC≡CH You may use any other required organic or inorganic reagents.

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Step by step solution

01

 Step 1: Reagents required for the synthesis

The synthesis reaction takes place in the presence of these reagents:

  • NaH: abstraction of an acidic proton
  • CH3CH2 Br: addition of alkyl group
  • Lindlar catalyst: reduction of alkyne to cis-alkene
  • HBr in the presence of peroxide: radical mechanism giving alkyl halide from an alkene
02

Stepwise mechanism

Step 1

Acidic hydrogen abstraction by NaH base

Step 2

Substitution of the alkyl group

Step 3

Reduction of alkyne

Step 4

Formation of alkyl halide following anti-Markovnikoff’s rule

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