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 answer
    D
    $\mathrm{CH}_3 \mathrm{COCl}$

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'.

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