JEE PYQ: Aldehydes And Ketones Question 10
Question 10 - 2021 (26 Feb Shift 2)
Identify A: $p$-methoxybenzaldehyde $\xrightarrow{\text{(i) HCHO, NaOH}}$ $\xrightarrow{\text{(ii) CH}_3\text{CH}_2\text{Br, NaH, DMF}}$ $\xrightarrow{\text{(iii) HI, }\Delta}$ A
(1). ($p$-HO-C$_6$H$_4$-C(=O)-OCH$_2$CH$_3$)
(2). ($p$-CH$_3$O-C$_6$H$_4$-CH$_2$OH)
(3). ($p$-CH$_3$O-C$_6$H$_4$-CH$_2$I (or the HI cleavage product))
(4). ($p$-HO-C$_6$H$_4$-CH$_2$OH)
Show Answer
Answer: (3)
Solution
Crossed Cannizzaro with HCHO/NaOH gives benzyl alcohol + HCOONa. Williamson ether synthesis with CH$_3$CH$_2$Br/NaH gives ethyl ether. HI/$\Delta$ cleaves the ether.
BETA
