Which of the following reagents/ reactions will convert 'A' to 'B'?
(A)PCC oxidation
(B)Ozonolysis
(C)BH3,H2O2/−OH followed by PCC oxidation✓ Correct
(D)HBr, hydrolysis followed by oxidation by K2Cr2O7.
Answer: (C)
Solution
The conversion requires anti-Markovnikov hydration of the alkene followed by oxidation. Hydroboration-oxidation (BH3,H2O2/−OH) adds OH in anti-Markovnikov fashion to give a primary alcohol, which is then oxidized by PCC to the aldehyde shown in B.
JEE Main · 2022 · 24 Jun 2022 · Shift 2 · Single correct option