JEE Main · 2006 · 30 Apr 2006 · Offline · General Organic Chemistry

The IUPAC name of the compound shown below is

(see structure)

(A)2-bromo-6-chlorocyclohex-1-ene
(B)6-bromo-2-chlorocyclohexene
(C)3-bromo-1-chlorocyclohexene✓ Correct
(D)1-bromo-3-chlorocyclohexene

Answer: (C)

Solution

For a cyclohexene the double bond fixes the numbering: its two carbons must be C1 and C2, and the ring is then numbered in whichever direction gives the substituents the lowest locants. Here the chlorine sits on one of the double-bond carbons, so it takes position 1, and the bromine falls on the neighbouring allylic carbon at position 3, a locant set of

{1, 3}

that cannot be bettered. Listing the substituents alphabetically, bromo before chloro, the compound is named 3-bromo-1-chlorocyclohexene.

JEE Main · 2006 · 30 Apr 2006 · Offline · Single correct option

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