An organic compound "P" of molecular formula C6H12O3 gives positive iodoform test but negative Tollens' test. When "P" is treated with dilute acid, it produces "Q". "Q" gives positive Tollens' test and also iodoform test. The structure of "P" is :
- H- O \|C-CH2-CH2- OCH3 |CH-OCH3
- CH3- O \|C- OCH3 |CH- OCH3 |CH2
- CH3- O \|C-CH2- OCH3 |CH-OCH3
- CH3- O \|C- OCH3 | OCH3 |C-CH3
Answer
(3) CH3- O \|C-CH2- OCH3 |CH-OCH3
Solution
P gives a positive iodoform test P contains CH3-CO-.
P gives a negative Tollens' test P has no free –CHO group.
Q (formed by dilute acid) gives a positive Tollens' test a –CHO group is set free on hydrolysis P contains an acetal group, -CH(OCH3)2.
For option (3): CH3COCH2CH(OCH3)2 ( C6H12O3 ✓)
CH3COCH2CH(OCH3)2 + H2O H+ CH3COCH2CHO + 2CH3OH
Q = CH3COCH2CHO has –CHO (Tollens' test positive) and CH3CO- (iodoform test positive). ✓
(1) has a free –CHO group (Tollens' test positive) and no CH3CO- group.
(2) contains only ether linkages, which are not hydrolysed by dilute acid no aldehyde is formed.
(4) is a ketal; hydrolysis gives CH3COCOCH3, a diketone with no –CHO group.
Answer: (3)