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NEET 2026
Exam
NEET
Year
2026
Subject
Chemistry
Chapter
Chapter

NEET 2026 · Chemistry · Chapter

What is the correct decreasing order of reactivity of the following...

What is the correct decreasing order of reactivity of the following alkyl halides towards sodium methoxide in a Williamson synthesis?

I. CH3−CH2−CH2−CH(Br)−CH3\mathrm{CH_3-CH_2-CH_2-CH(Br)-CH_3}
II. CH3−CH2−CH(CH3)−CH2−Br\mathrm{CH_3-CH_2-CH(CH_3)-CH_2-Br}
III. C6H5−CH2−Br\mathrm{C_6H_5-CH_2-Br}
IV. CH3−CH2−CH2−CH2−Br\mathrm{CH_3-CH_2-CH_2-CH_2-Br}

Options

  1. AI >> II >> IV >> III
  2. BIII >> II >> IV >> I
  3. CIII >> IV >> II >> I
  4. DIV >> III >> II >> I

Correct answer

C. III >> IV >> II >> I

Step-by-step solution

Williamson ether synthesis proceeds via an SN2S_N2 mechanism.

The rate of an SN2S_N2 reaction is inversely proportional to the steric hindrance around the electrophilic carbon and is enhanced by the stabilization of the transition state.

Compound III (C6H5−CH2−Br\mathrm{C_6H_5-CH_2-Br}) is a benzylic halide. Its SN2S_N2 transition state is highly stabilized by the adjacent phenyl ring through conjugation, making it the most reactive.

Compound IV (CH3−CH2−CH2−CH2−Br\mathrm{CH_3-CH_2-CH_2-CH_2-Br}) is an unbranched primary alkyl halide with minimal steric hindrance.

Compound II (CH3−CH2−CH(CH3)−CH2−Br\mathrm{CH_3-CH_2-CH(CH_3)-CH_2-Br}) is a primary alkyl halide but has a methyl group at the β\beta-position. This branching increases steric hindrance, making it less reactive than IV.

Compound I (CH3−CH2−CH2−CH(Br)−CH3\mathrm{CH_3-CH_2-CH_2-CH(Br)-CH_3}) is a secondary alkyl halide, which is more sterically hindered at the α\alpha-carbon than primary alkyl halides, making it the least reactive.

Therefore, the decreasing order of reactivity is III >> IV >> II >> I.

Answer: III >> IV >> II >> I
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