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
- (a) A-CH₃CH₂CH=CH-CH₃, B-CH₃CH₂CH₂CH=CH₂, Saytzeff products
- (b) A-CH₃CH₂CH=CH-CH₃, B -CH₃CH₂CH₂CH=CH₂, Hofmann products
- (c) A-CH₃CH₂CH₂CH=CH₂, B-CH₃CH₂CH=CHCH₃, Hofmann products
- (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.
- 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 used Hydrogens there Alkene formed Product C1 (CH₃) 3, primary, exposed CH₃CH₂CH₂CH=CH₂, less substituted A, major (Hofmann) C3 (CH₂) 2, secondary, more crowded CH₃CH₂CH=CHCH₃, more substituted B, minor (Saytzeff) - 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.
- 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.