Chapter 11: 45bE (page 350)

How might you prepare each of the following molecules using a nucleophilic substitution reaction at some step?

Short Answer

Expert verified

$C H_{3} B r +^{-} O - C {(C H_{3})}_{3} \to C H_{3} - O - C {(C H_{3})}_{3} + N a B r$

$C H_{3} O H + C l - C {(C H_{3})}_{3} \to C H_{3} - O - C {(C H_{3})}_{3} + {(C H_{3})}_{3} C = C H_{2}$

Step by step solution

SN2reaction

It is a nucleophilic substitution reaction in which an old bond is broken and 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.

$C H_{3} B r +^{-} O - C {(C H_{3})}_{3} \to C H_{3} - O - C {(C H_{3})}_{3} + N a B r$

Substitution reaction

E2reaction

It is a nucleophilic elimination reaction in which an old bond is broken and 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.

$C H_{3} O H + C l - C {(C H_{3})}_{3} \to C H_{3} - O - C {(C H_{3})}_{3} + {(C H_{3})}_{3} C = C H_{2}$