Q47 / 200 · NEET 2010 (Screening) · Chemistry
Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
- A$\mathrm{CH}_3 \mathrm{COOCH}_3$
- B$\mathrm{CH}_3 \mathrm{CONH}_2$
- C$\mathrm{CH}_3 \mathrm{COOCOCH}_3$
- Correct answerD$\mathrm{CH}_3 \mathrm{COCl}$
Solution
Key Idea Lesser the electron density of acyl carbon atom, more will be the susceptibility of nucleophile to attack it.
The $\mathrm{Cl}$ atom has strong $-I$ effect and weakest $+\mathrm{R}$ effect because of the weak $\pi$-bond between the small sized $\mathrm{C}$-atom and large sized $\mathrm{Cl}$ atom. Thus, in $\mathrm{CH}_3 \mathrm{COCl}$, acyl carbon has least electron density and hence, more susceptible for nucleophilic attack.
Hence, the correct answer is option: 'D'.