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JEE Main levelSingle correct optionDifficulty 2 of 3o3073

Hypothetical relative rate constants for SN2 reaction of with iodide in acetone (ethyl bromide ) are: 1.00; 0.40; 0.030; . From these data, isobutyl bromide is faster than neopentyl bromide by a factor of, and the trend shows that

  1. A; beta-branching has little effect until the carbon becomes tertiary
  2. B; isobutyl bromide is slower because it has fewer beta-methyl groups
  3. C; each additional beta-methyl group slows the reaction by the same factor
  4. D; each additional beta-methyl group slows the reaction, the third one by far the most

Answer: D

The ratio is . The successive factors are 2.5 (ethyl to propyl), 13.3 (propyl to isobutyl) and 3000 (isobutyl to neopentyl), so the retardation grows sharply with each added beta-methyl group as the backside is progressively blocked.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN2 mechanism, rate, stereochemistry, steric effects

More questions on SN2 mechanism, rate, stereochemistry, steric effects