JEE Main 2020 · 2 September · evening · Single correct · +4 / −1
The major product obtained from E₂ - elimination of 3-bromo-2-fluoropentane is
- (a) CH₃CH₂-C(|(Br))H-CH=CH₂
- (b) CH₃-CH₂-C(Br; |)=CH-CH₃
- (c) CH₃CH₂CH=, C, -F; |; CH₃
- (d) F; |; CH₃, -, CH, =, CH, -, CH, -, CH₃
Answer and solution
Answer (c) CH₃CH₂CH=, C, -F; |; CH₃
Solution
Chemistry ma’am · 4 steps
Bromide leaves, fluorine stays, and the base pulls off the H next to fluorine.
- Draw the chain. 3-bromo-2-fluoropentane is CH₃-CHF-CHBr-CH₂-CH₃. Fluorine sits on C2 and bromine on C3.
- Pick the leaving group. The C-Br bond is much weaker than the C-F bond, and Br⁻ is a far better leaving group than F⁻. So the molecule loses HBr, and F stays in the product.
- Choose the β-hydrogen. The carbons next to C3 are C2 and C4, so the H can come from either. The H on C2 is more acidic because the electronegative F beside it pulls electron density away (−I effect). Removing it also gives the more substituted alkene, CH₃-CF=CH-CH₂CH₃.
Option Lost β-H taken from Verdict (a) HF C1 F cannot leave in preference to Br (b) HF C3 F cannot leave in preference to Br (c) HBr C2, next to F acidic H, trisubstituted alkene: major (d) HBr C4 less acidic H, disubstituted alkene: minor - So. The major product is 2-fluoropent-2-ene, CH₃CH₂CH=C(F)CH₃, which is option (c).
The idea to keep. In E2 the halogen with the weaker C–X bond leaves, so Br goes and F stays. A β-H next to an electronegative atom is more acidic, and pulling it off here also gives the more substituted alkene.
Answer from the NTA final answer key. Solution by PrepWiser.