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NEET CHEMISTRYMedium

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 (RMgXRMgX) on the strained epoxide ring of ethylene oxide (oxirane).

  1. Mechanism: The alkyl group (RR^-) 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.
  2. Hydrolysis: Subsequent acid hydrolysis of the intermediate yields a primary alcohol.
  3. 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: CH2OCH2Ethylene oxide+RMgXRCH2CH2OMgXH3O+RCH2CH2OHPrimary Alcohol\underset{\text{Ethylene oxide}}{CH_2-O-CH_2} + RMgX \rightarrow R-CH_2-CH_2-OMgX \xrightarrow{H_3O^+} \underset{\text{Primary Alcohol}}{R-CH_2-CH_2-OH}
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