Ethylene oxide when treated with Grignard reagent yields:
A
Secondary alcohol
B
Tertiary alcohol
C
Cyclopropyl alcohol
D
Primary alcohol
Step-by-Step Solution
The reaction involves the nucleophilic attack of the Grignard reagent (RMgX) on the strained epoxide ring of ethylene oxide (oxirane).
Mechanism: The alkyl group (R−) of the Grignard reagent acts as a nucleophile and attacks one of the carbon atoms of the ethylene oxide ring, causing the ring to open. This forms a magnesium alkoxide intermediate.
Hydrolysis: Subsequent acid hydrolysis of the intermediate yields a primary alcohol.
Chain Lengthening: The resulting primary alcohol has a carbon chain that is two carbon atoms longer than the alkyl group of the original Grignard reagent.
Reaction: Ethylene oxideCH2−O−CH2+RMgX→R−CH2−CH2−OMgXH3O+Primary AlcoholR−CH2−CH2−OH
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