JEE Main 2020 · 2 September · evening · Single correct · +4 / −1

The major product obtained from E₂ - elimination of 3-bromo-2-fluoropentane is

  1. (a) CH₃CH₂-C(|(Br))H-CH=CH₂
  2. (b) CH₃-CH₂-C(Br; |)=CH-CH₃
  3. (c) CH₃CH₂CH=, C, -F; |; CH₃
  4. (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.

  1. Draw the chain. 3-bromo-2-fluoropentane is CH₃-CHF-CHBr-CH₂-CH₃. Fluorine sits on C2 and bromine on C3.
  2. 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.
  3. 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.
    OptionLostβ-H taken fromVerdict
    (a)HFC1F cannot leave in preference to Br
    (b)HFC3F cannot leave in preference to Br
    (c)HBrC2, next to Facidic H, trisubstituted alkene: major
    (d)HBrC4less acidic H, disubstituted alkene: minor
  4. 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.

Study Halogen Derivatives — Haloalkanes & Haloarenes

Asked about 120 times in JEE Main since 2020. This question is from 2020.