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(A)(C(9)H(12)O)underset(Hot KMnO(4))over...

(A)`(C_(9)H_(12)O)underset(Hot KMnO_(4))overset([O])(rarr) PhCOOH`
i. (A) does not decolourise `Br_(2)` in `C Cl_(4)`, reacts with Na to give a colourless and odourless gas (B).
ii. (A) does not give iodoform test.
iii. (A) is a chiral compound and oxidation of (A) with `CrO_(3)//Py` gives a chiral compound (C ).
iv. The colour of `Cr_(2)O_(7)^(2-)` change to blue-green when added to compound (A).
The structure of compound (A) is:

A

a.

B

b.

C

c.

D

d.

Text Solution

Verified by Experts

The correct Answer is:
C
`DU` in `A=((2n_(C )+2)-n_(H))/2=((2xx4+2)-8)/2=1^(@)`
(Due to `(-COOH)` group)
Compount (B) is unstable and losed `CO_(2)`, it shows (B) must contain beta-keto acid, which account for three oxygen atoms in (A) and (B).
(A) must contain beta-hydroxy acid which on oxidation with `PC C` gives (B) `(beta-"keto acid")`.
Therefore, structure of (A) `implies`

Conversion of `MeCHO` to `MeCOMe` (Acetone):
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