Q49bE - Organic Chemistry (Mcmurry)

Question

Question:  Propose structures for compounds that fit the following descriptions:

(b) An organohalide that will not undergo nucleophilic substitution

Step-by-Step Solution

Answer

Answer: 

$C{H}_2=CHBr$ like other in vinylic organohalide do not show the nucleophilic substitution      

Step 1: S N 1 reaction

It is a nucleophilic substitution reaction in which an old bond is broken and a new bond is formed both processes occur simultaneously. Hence, it’s a single-step reaction.

The two reacting species are involved in the rate-determining steps.

Step 2: E 2 reaction

It is a nucleophilic elimination reaction in which an old bond is broken and a new bond is formed both the process occur simultaneously and no intermediate is formed.

Here, the carbon-hydrogen or halogen bond breaks to form a new double bond. Hence, it’s a single-step reaction.

Step 3: Formation of alkene

Organohalide is the vinylic halide that already has a double bond so these compounds do not show any nucleophilic substitution reactions.

Like $C{H}_2=CHBr$