JEE PYQ: Aldehydes And Ketones Question 40
Question 40 - 2019 (11 Jan Shift 1)
Compound with CN and OEt (ester) $\xrightarrow{\text{(i) Ni/H}_2, \text{(ii) DIBAL-H}}$ ?
(1). (CHO + NH product)
(2). (Tetrahydroisoquinoline (cyclic amine))
(3). (OH + NH$_2$ product)
(4). (Isoquinoline)
Show Answer
Answer: (2) (Note: Answer key says 3)
Solution
Ni/H$_2$ reduces C=C and CN to CH$_2$NH$_2$. DIBAL-H reduces ester to CHO. Intramolecular cyclization of amine with aldehyde forms tetrahydroisoquinoline.
BETA
