IIT-JEE 2009 · Paper 1 · Chemistry Q8

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ChemistrySingle correct+3 / -1Question 8 of 60

The IUPAC name of the following compound is

A benzene ring bearing OH at the top, CN on the ring carbon meta to OH, and Br on the carbon para to OH (adjacent to the CN carbon).

4-Bromo-3-cyanophenol

2-Bromo-5-hydroxybenzonitrile

2-Cyano-4-hydroxybromobenzene

6-Bromo-3-hydroxybenzonitrile

Answer and worked solution

Official answer: B

Principal group. Of -CN, -OH and -Br, the nitrile has the highest priority, so the parent is benzonitrile and the CN carbon is C1.

Numbering. Going round the ring towards Br: Br on C2, OH on C5 (lowest locants {2,5}). Substituents in alphabetical order:
$\text{2-bromo-5-hydroxybenzonitrile}.$

(B)

Topics:IUPAC nomenclature

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IIT-JEE 2009 · Paper 1, Chemistry question 8