Q24 / 120 · VITEEE 2016 · Chemistry

Figure
can't give decarboxylation while normally $\alpha-\beta$ unsaturated acid give this reaction because

  • A
    t-butyl gp. has large size and does not let the $\mathrm{COOH}$ group to leave.
  • B
    t-butyl gp. can't extract $\mathrm{H}$ from $\mathrm{COOH}$.
  • Correct answer
    C
    t-butyl gp. stabilise carbanion formed.
  • D
    t-butyl gp. does not allow this composition to convert to $\beta$ - $\gamma$-unsaturated acid

Solution

Because of +I effect, t-butyl group destabilises the carbanion.

Hence, the correct answer is option: 'C'.

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