In the following reaction sequence, predict the compounds X and Y: [Guj CET 2008] 4 -methylaniline ( p -toluidine) Excess Br_2 X [ (ii) H_3PO_2] (i) NaNO_2/HCl Y

JEE Main Chemistry question

In the following reaction sequence, predict the compounds and : [Guj CET 2008]

4-methylaniline (p-toluidine) X Y

(A) = 4-amino-3,5-dibromotoluene; = 3,5-dibromotolueneCorrect
(B) = 4-amino-2,6-dibromotoluene; = 2,6-dibromotoluene
(C) = 4-amino-3-bromotoluene; = 3-bromotoluene
(D) = 2,4,6-tribromoaniline; = 1,3,5-tribromobenzene

Answer: (A)

Solution

Excess bromine brominates both positions ortho to the strongly activating group of -toluidine (positions 3 and 5 relative to ), giving 4-amino-3,5-dibromotoluene () — equivalently described as 2,6-dibromo-4-methylaniline when numbered from the

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Question ID VK-150296