a. Isomers (A) and (B), `C_(10)H_(12)O`, are isolated form the oil of bay leaf. They are insoluble in aq. NaOH and decolourise `Br_(2)//CCI_(4)` and `KMnO_(4)`. Each is vigorously oxidised to p-anisic acid, `(p-MeOC_(6)H_(4)COOH)`. Ozonolysis (A) and (B).
b. Give the structure of a third isomer (C) that is also oxidised to p-anisic as do (A) and (B).
c. Suggest a chemical reaction that can distinguish (C) from (A) and (B).

Explanation

a.
i. Five DU in A and B `(C:H=1:1)` suggest benzene ring (4 DU) and one `(C=C)` bond, since it decolou-rises `Br_(2)` solution and cold alkaline `KMnO_(4)` solution.
ii. (A) and (B) `overset (O_(3)//Red) rarr` Same product
It suggests that (A) and (B) are geometrical isomers.
iii. (A) and (B) `overset ([O]) rarr`

b.
c.