Question Details

Find out product (X)

Options

A

B

C

D

Correct Answer :

Ph - CH2 - CH2 - CH2 - OH

Solution :

The correct answer is:
PhCH2CH2CH2OH

Let us break down the reaction sequence step-by-step:

Step 1: Hydroboration-Oxidation of Styrene
The starting material shown in the image is styrene:
PhCH=CH2
When treated with diborane in tetrahydrofuran (B2H6/THF) followed by alkaline hydrogen peroxide (H2O2/OH), the alkene undergoes hydroboration-oxidation. This reaction is an anti-Markovnikov addition of water across the double bond, where the hydroxyl group (OH) attaches to the less substituted terminal carbon. This yields 2-phenylethan-1-ol:
PhCH2CH2OH

Step 2: Substitution with HBr
The alcohol 2-phenylethan-1-ol is then treated with hydrobromic acid (HBr). The hydroxyl group is protonated to form water (a good leaving group), which is substituted by the bromide ion (Br). This converts the alcohol into an alkyl halide, 2-phenylethyl bromide:
PhCH2CH2Br

Step 3: Grignard Reagent Formation
The alkyl halide is reacted with metallic magnesium (Mg) in dry ether. The magnesium inserts into the carbon-halogen bond to form a nucleophilic Grignard reagent, 2-phenylethylmagnesium bromide:
PhCH2CH2MgBr

Step 4: Reaction with Formaldehyde (HCHO)
The nucleophilic carbon of the Grignard reagent attacks the electrophilic carbonyl carbon of formaldehyde (HCHO). This nucleophilic addition adds one carbon atom to the chain and forms an alkoxide intermediate:
PhCH2CH2CH2OMgBr+
Subsequent acidic workup protonates the alkoxide, yielding the primary alcohol product (X), 3-phenylpropan-1-ol:
PhCH2CH2CH2OH

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