JEE · NEET Previous Year Question

An organic compound " P " of molecular formula gives positive Iodoform test but negative Tollen's test. When " P " is treated with dilute acid, it produces " Q ". " Q " gives positive Tollen's test and also iodoform test. The structure of " P " is:

Topic: JEE PYQ

Answer: A. Full step-by-step solution below.

  1. A
  2. B
  3. C
  4. D

Correct answer: A

Solution

(a) P gives positive iodoform (has ) but negative Tollen's (no -CHO).
Q (after acid hydrolysis) gives both tests, meaning Q has both and -CHO .
This indicates P has an acetal protecting an aldehyde group.
Option (a):
Has positive iodoform
Has acetal , no free aldehyde → negative Tollen's
Hydrolysis:
gives both iodoform and Tollen's test
Molecular formula:

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