1-Bromo-4-methylbenzene is nitrated with a mixture of concentrated HNO3 and H2SO4 at low temperature. The major mononitro product is

4-bromo-1-methyl-2-nitrobenzene (nitro group ortho to methyl)

1-bromo-4-methyl-2-nitrobenzene and 4-bromo-1-methyl-2-nitrobenzene in equal amounts

1-bromo-4-methyl-2-nitrobenzene (nitro group ortho to bromine)

2-bromo-5-methyl-1-nitrobenzene

4-bromo-1-methyl-2-nitrobenzene (nitro group ortho to methyl)

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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc160

1-Bromo-4-methylbenzene is nitrated with a mixture of concentrated $HNO X_{3}$ and $H X_{2} SO X_{4}$ at low temperature. The major mononitro product is

A1-bromo-4-methyl-2-nitrobenzene and 4-bromo-1-methyl-2-nitrobenzene in equal amounts
B1-bromo-4-methyl-2-nitrobenzene (nitro group ortho to bromine)
C2-bromo-5-methyl-1-nitrobenzene
D4-bromo-1-methyl-2-nitrobenzene (nitro group ortho to methyl)

Answer: D

Both

- CH X_{3}

and

- Br

are ortho/para directors, and the para positions are blocked, so substitution is ortho to one of them. The activating methyl group, which donates by hyperconjugation and induction, outweighs the deactivating bromine and controls the position. Nitration occurs ortho to methyl: 4-bromo-1-methyl-2-nitrobenzene.

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1-Bromo-4-methylbenzene is nitrated with a mixture of concentrated HNOX3​ and HX2​SOX4​ at low temperature. The major mononitro product is

Answer: D

More questions on Aromatic hydrocarbons: benzene reactions and side chain reactions

1-Bromo-4-methylbenzene is nitrated with a mixture of concentrated $HNO X_{3}$ and $H X_{2} SO X_{4}$ at low temperature. The major mononitro product is