JEE PYQ: Aromatic Compounds Question 8
Question 8 - 2020 (05 Sep Shift 1)
In the following reaction sequence the major products A and B are:
Toluene + phthalic anhydride $\xrightarrow{\text{anhyd. AlCl}_3}$ A $\xrightarrow{1. \text{Zn-Hg/HCl}, 2. \text{H}_3\text{PO}_4}$ B
(1) A = keto-acid; B = anthracenedione
(2) A = keto-acid; B = anthracenone
(3) A = keto-acid; B = different anthracenone
(4) A = keto-acid; B = yet another isomer
Show Answer
Answer: (2)
Solution
Friedel-Crafts acylation gives keto-acid (A), Clemmensen reduction then intramolecular cyclization with $\text{H}_3\text{PO}_4$ gives anthracenone (B).
BETA
