JEE Main · 2023 · 15 Apr 2023 · Shift 1 · Hydrocarbons

The product formed in the following multistep reaction is:

(A)(see structure)
✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)

Answer: (A)

Solution

Propene first undergoes hydroboration with diborane followed by oxidation with alkaline hydrogen peroxide; water adds against Markovnikov's rule, placing the hydroxyl on the terminal carbon to give propan-1-ol. PCC is a mild oxidant that converts this primary alcohol to the aldehyde propanal without over-oxidation to the acid. Addition of methylmagnesium bromide to propanal, followed by aqueous work-up, lengthens the chain by one carbon and gives a secondary alcohol. The product is butan-2-ol,

C H_{3} C H_{2} CH (OH) C H_{3}

JEE Main · 2023 · 15 Apr 2023 · Shift 1 · Single correct option

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