JEE Main 2016 · 10 Apr · Shift 1 · Chemistry Q53

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ChemistrySingle correct+4 / -1Question 53 of 90

Consider the reaction sequence below :

X is :

Anisole treated with succinic anhydride/AlCl₃ to give A, then Clemmensen reduction to give X.

6-Methoxytetralin-1,4-diol

Tetralin (1,2,3,4-tetrahydronaphthalene) with OH on C1 and C4 and OCH₃ on C6.

5-Methoxytetralin-1,4-diol

Tetralin (1,2,3,4-tetrahydronaphthalene) with OH on C1 and C4 and OCH₃ on C5.

5-Methoxytetralin

Tetralin (1,2,3,4-tetrahydronaphthalene) with OCH₃ on C5.

6-Methoxytetralin

Tetralin (1,2,3,4-tetrahydronaphthalene) with OCH₃ on C6.

Answer and worked solution

Official answer: D

Friedel-Crafts acylation of anisole with succinic anhydride gives 4-(4-methoxyphenyl)-4-oxobutanoic acid, and Clemmensen reduction removes the ketone to give 4-(4-methoxyphenyl)butanoic acid. That acid is not among the options; the classic continuation (intramolecular acylation and a second reduction) leads to 6-methoxytetralin, structure (4), which this derived key takes as X.

Topics:Oxidation and reduction Aromatic hydrocarbons and electrophilic substitution

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JEE Main 2016 · 10 Apr · Shift 1, Chemistry question 53