Question

What is true regarding the following acid catalyzed esterification (Fischer) reaction ?
$C{H}_{3}C{H}_{2}COOH+C{H}_{3}C{H}_{2}OH\stackrel{H^{+}}{⟶}C{H}_{3}C{H}_{2}COO{C}_2{H}_5$

• A. The reaction involves production on $s{p}^3$-oxygen of acid in the first step
• B. The reaction involves protonation on $s{p}^2$-oxygen of acid followed by formation of acylium ion $\left(RO{C}^{+}\right)$ in the first step
• C. The slowest step of reaction is the nucleophilic attack of alcohol on $s{p}^2$ carbon of acid
• D. Alcohol undergoes protonation in the first step

Answer 1

Answer: (A), (C)

The correct options are
A The reaction involves production on $s{p}^3$-oxygen of acid in the first step
C The slowest step of reaction is the nucleophilic attack of alcohol on $s{p}^2$ carbon of acid

A) Not true,in first step reaction occurs on $s{p}^2$-oxygen of acid

B) Not true,after protonation of $s{p}^2$-oxygen,next $R{O}^{+}H$ is formed.

C) True, nucleophilic attack on $s{p}^2$ carbon is slowest step.

D) Not true, carboxyl group gets protonation in first step