A student is given one compound among the following compounds that gives positive test with Tollens' reagent. [figure] The compound is :
- B
- D
- A
- C
Answer
(4) C
Solution
Tollens' test is given by compounds having a free –CHO group (or giving one easily in solution).
C is a cyclic hemiacetal (2-hydroxytetrahydrofuran, –O–CH(OH)– in the ring). In solution it is in equilibrium with its open-chain form, 4-hydroxybutanal:
C4H8O2 (cyclic hemiacetal) HO-CH2-CH2-CH2-CHO
The free –CHO group reduces Tollens' reagent to a silver mirror positive test.
A is a cyclic acetal (–O–CH(OCH3)–); acetals are stable in basic medium and do not open negative.
B is an ether and D is a simple secondary alcohol (OH on C-3, not on the carbon next to ring O) no –CHO, negative.
The compound is C.
Answer: (4)