45dE - Organic Chemistry (Mcmurry)

Question

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

$d.C{H}_{3}C{H}_{2}C{H}_{2}C{H}_{2}N{H}_2$

Step-by-Step Solution

Answer

$C{H}_{3}C{H}_{2}C{H}_{2}C{H}_{2}Br+\left(excess\right)N{H}_3\to C{H}_{3}C{H}_{2}C{H}_{2}C{H}_{2}N{H}_2+NaBr$

S N 2 reaction

It is a nucleophilic substitution reaction in which old bond is break and new bond is formed both the process occur simultaneously. Hence, it’s a single step reaction.

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

Formation of C H 3 C H 2 C H 2 C H 2 N H 2

Here, the nucleophilic substitution occur where NaBr is produced and desired product is formed.

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

$C{H}_{3}C{H}_{2}C{H}_{2}C{H}_{2}Br+excessN{H}_3\to C{H}_{3}C{H}_{2}C{H}_{2}C{H}_{2}N{H}_2+NaBr$

                                                   Substitution reaction