Q.11-50c - Organic Chemistry (Mcmurry)

Question

Question: What products would you expect from the reaction of 1-bromopropane with each of the following? 

(c)  NaI

Step-by-Step Solution

Answer

Answer

$$\begin{gathered} {\text{CH}}_3{\text{CH}}_2{\text{CH}}_2{\text{Br+Nal→CH}}_3{\text{CH}}_2{\text{CH}}_2\text{l+NaBr} \\ \text{ Substitution reaction} \end{gathered}$$

Step1: S N 2 reaction

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

Two reacting species are involved in the rate-determining steps. 

Step2: Reaction of CH 3 CH 2 CH 2 Br+Nal

It is a substitution reaction in which C-Br is broken, and the C-I bond is formed in a single-step process, which means the iodide ion substitutes for the bromide ion. Hence, a substitution reaction and bromide and iodide are nucleophiles’ so-called nucleophilic substitution reactions. 

 $$\begin{gathered} {\text{CH}}_3{\text{CH}}_2{\text{CH}}_2{\text{Br+Nal→CH}}_3{\text{CH}}_2{\text{CH}}_2\text{l+NaBr} \\ \text{ Substitution reaction} \end{gathered}$$