JEE Main 2022 · 28 July · morning · Single correct · +4 / −1

Identify the correct statement for the below given transformation.
CH₃-CH₂-CH₂-CH-CH₃ →(C₂H₅ONa) A + B

  1. (a) A-CH₃CH₂CH=CH-CH₃, B-CH₃CH₂CH₂CH=CH₂, Saytzeff products
  2. (b) A-CH₃CH₂CH=CH-CH₃, B -CH₃CH₂CH₂CH=CH₂, Hofmann products
  3. (c) A-CH₃CH₂CH₂CH=CH₂, B-CH₃CH₂CH=CHCH₃, Hofmann products
  4. (d) A-CH₃CH₂CH₂CH=CH₂, B-CH₃CH₂CH=CHCH₃, Saytzeff products
Answer and solution

Answer (c) A-CH₃CH₂CH₂CH=CH₂, B-CH₃CH₂CH=CHCH₃, Hofmann products

Solution

Chemistry ma’am · 3 steps

A bulky, positively charged leaving group means the Hofmann rule: the less substituted alkene wins.

  1. Find the β-hydrogens. The -N⁺(CH₃)₃ group sits on C2 of a pentane chain. Ethoxide can remove a β-hydrogen from C1 (a CH₃) or from C3 (a CH₂), and N(CH₃)₃ leaves.
    β-carbon usedHydrogens thereAlkene formedProduct
    C1 (CH₃)3, primary, exposedCH₃CH₂CH₂CH=CH₂, less substitutedA, major (Hofmann)
    C3 (CH₂)2, secondary, more crowdedCH₃CH₂CH=CHCH₃, more substitutedB, minor (Saytzeff)
  2. Why Hofmann here. -N⁺(CH₃)₃ is bulky, so the base reaches the open CH₃ hydrogens more easily. It is also a poor leaving group, so the C–H bond breaks well before the C–N bond. That builds negative charge on the β-carbon, and a primary carbon carries that charge best.
  3. So. The major product A is pent-1-ene and the minor product B is pent-2-ene. Because the less substituted alkene is the major product, these are Hofmann products, which is option (c).

The idea to keep. When the leaving group is -N⁺(CH₃)₃ or another bulky, charged group, expect the Hofmann alkene. The base pulls the most accessible, most acidic β-H, usually from a CH₃.

Answer from the NTA final answer key. Solution by PrepWiser.

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Asked about 170 times in JEE Main since 2020. This question is from 2022.