Indian Forest Service (Mains), Chemistry optional · 2025 · Paper II
Q1(d). Elimination next to an existing alkene
Question
Give major and minor products of the drawn bromide with methoxide. [structure of the bromide, CH₂=CHCH₂CH(Br)CH(CH₃)₂, given in the paper]
Answer in brief
Major: CH₂=CHCH=CHCH(CH₃)₂; minor: CH₂=CHCH₂CH=C(CH₃)₂.
Key points
- Read the substrate as CH₂=CHCH₂CH(Br)CH(CH₃)₂; methoxide can remove a β H on either side of the brominated carbon.
- Removal from the CH₂ next to the original alkene creates a conjugated 1,3-diene; conjugation favours this route despite the competing alkene being more substituted.
- Removal from the isopropyl methine gives the isolated, more substituted double bond: a non-conjugated 1,4-diene.
- E2 elimination requires the C–H and C–Br bonds to be anti-periplanar; acyclic bond rotation permits both productive conformations.
The full model answer
As written for the answer booklet: the diagram carries the working, the lines stay short. Read here only; it is not offered as a download.

CoversE2 eliminationconjugated dieneSaytzeff vs Hofmannanti-periplanardehydrohalogenation
All parts of Question 1
- 1(a) Aromaticity of small rings5 marks
- 1(b) Nitrene transfer to an alkene5 marks
- 1(c) Electrophilic substitution of heteroarenes5 marks
- 1(d) Elimination next to an existing alkene5 marks
- 1(e) Oxymercuration of norbornene5 marks
- 1(f) Medium-dependent pinacol rearrangement5 marks
- 1(g) Two thermal electrocyclic steps5 marks
- 1(h) Intramolecular Claisen condensation5 marks