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← JEE Advanced 2013 · Paper 2
ChemistryMultiple correct+3 / -1Question 27 of 60

JEE Advanced 2013 · Paper 2, Chemistry question 27

The major product(s) of the following reaction is(are)

4-Hydroxybenzenesulphonic acid treated with aqueous Br₂ (3.0 equivalents) gives ?Candidate products: P 2,3,5-tribromo-4-hydroxybenzenesulphonic acid (Br at both positions ortho to OH and one meta to OH); Q 2,4,6-tribromophenol; R 3,4,5-tribromophenol; S 2,3,6-tribromo-4-hydroxybenzenesulphonic acid drawn with Br on both carbons flanking SO₃H and one ortho to OH.
Choose one or more options
Answer and worked solution

Official answer: B

Ipso substitution. The -OH strongly activates the ring. Bromine water substitutes both ortho positions, and the SO₃H para to OH is displaced by Br⁺ (desulphonation), giving 2,4,6-tribromophenol (Q).

(B)

Topics:PhenolsAromatic hydrocarbons and electrophilic substitution
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