What is the order of reactivity of alkyl halides with ammonia?

What is the order of reactivity of alkyl halides with ammonia?
  1. $\mathrm{R}-\mathrm{Cl}>\mathrm{R}-\mathrm{Br}>\mathrm{R}-\mathrm{I}$
  2. $\mathrm{R}-\mathrm{Br}>\mathrm{R}-\mathrm{I}>\mathrm{R}-\mathrm{Cl}$
  3. R-I $>$ R-Br $>$ R-Cl
  4. $\mathrm{R}-\mathrm{Cl}>\mathrm{R}-\mathrm{I}>\mathrm{R}-\mathrm{Br}$

Solution

Reactivity of alkyl halides with ammonia depends on nucleophilic substitution mechanisms, where ammonia acts as a nucleophile. The key factor is the leaving group ability of the halide ion.

Leaving group ability is inversely related to basicity. Comparing halides: iodine is the weakest base and thus the best leaving group, followed by bromine and then chlorine. This gives the order I- > Br- > Cl- for leaving group quality.

Consequently, alkyl halide reactivity follows: $\mathrm{R}{-}\mathrm{I} > \mathrm{R}{-}\mathrm{B} > \mathrm{R}{-}\mathrm{Cl}$.

Evaluating the options:
A) $\mathrm{R}{-}\mathrm{Cl} > \mathrm{R}{-}\mathrm{B} > \mathrm{R}{-}\mathrm{I}$ (Incorrect)
B) $\mathrm{R}{-}\mathrm{B} > \mathrm{R}{-}\mathrm{I} > \mathrm{R}{-}\mathrm{Cl}$ (Incorrect)
C) $\mathrm{R}{-}\mathrm{I} > \mathrm{R}{-}\mathrm{B} > \mathrm{R}{-}\mathrm{Cl}$ (Correct)
D) $\mathrm{R}{-}\mathrm{Cl} > \mathrm{R}{-}\mathrm{I} > \mathrm{R}{-}\mathrm{B}$ (Incorrect)

Answer: $\boxed{\text{C}}$

Asked in: MHT CET 2025 (05 May Shift 2)

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