3P - Organic Chemistry (Mcmurry)

Question

Show the mechanism of the following nucleophilic acyl substitution reaction, using curved arrows to indicate the electron flow in each step:

Step-by-Step Solution

Answer

The mechanism of nucleophilic acyl substitution reaction has been explained below.

Step 1: Steps for the reaction mechanism

The general mechanism is divided into two steps:

1) Nucleophilic attack

2) Lon of the leaving group

Step 2: Mechanism of the reaction

The attack of the nucleophile on the carbonyl group which leaves the $\mathrm{C}=\mathrm{O} \mathrm{\pi }$ bond will leads to the formation of a tetrahedral intermediate with C-Nu bond. The potential elimination will leave group z which restores the $\mathrm{C}=\mathrm{O} \mathrm{\pi }$ bond and will lead to the formation of substitution of products and also for hybridization.

The attack of nucleophile methoxide on the carbonyl carbon, which gives leaving group as chloride ion, a very weak base.