JEE Advanced levelSingle correct optionDifficulty 3 of 3o4146
Propanal (2 mol) is treated with dilute NaOH and heated. The product obtained after dehydration is
A2-methylpent-2-enal
B3-methylpent-2-enal
Chex-2-enal
D2-methylpent-2-en-1-ol
Answer: A
The enolate of propanal adds to a second propanal to give 3-hydroxy-2-methylpentanal. Its alpha carbon still has one H, so E1cB loss of OHX− gives the conjugated aldehyde CHX3CHX2CH=C(CHX3)CHO, 2-methylpent-2-enal.