'x' is the product which is obtained from propanenitrile and stannous chloride in the presence of hydrochloric acid followed by hydrolysis. 'y' is the product which is obtained from the but-2-ene by the ozonolysis followed by hydrolysis. From the following, which product is not obtained when one mole of 'x' and one mole of 'y' react with each other in the presence of alkali followed by heating?
- 2-Methylpent-2-enal
- 2-Methylbut-2-enal
- 3-Methylbut-2-enal
- Pent-2-enal
Answer
(3) 3-Methylbut-2-enal
Solution
Stephen reaction: CH3CH2C N [H3O+]SnCl2/HCl CH3CH2CHO x = propanal
Ozonolysis: CH3CH=CHCH3 [Zn/H2O]O3 2 CH3CHO y = ethanal
Both have α-hydrogens, so dilute alkali and heat give four aldol condensation products:
Ethanal + ethanal CH3CH=CHCHO (but-2-enal)
Propanal + propanal CH3CH2CH=C(CH3)CHO (2-methylpent-2-enal)
Enolate of propanal + ethanal CH3CH=C(CH3)CHO (2-methylbut-2-enal)
Enolate of ethanal + propanal CH3CH2CH=CHCHO (pent-2-enal)
3-Methylbut-2-enal, (CH3)2C=CHCHO, would need acetone as the carbonyl partner, so it is not formed.
Answer: (3)