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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

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}

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersethylenetreatedgrignardreagentyields

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