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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

The reaction: CH3CH(CH3)CH2OCH2CH3+HIheated?CH_3-CH(CH_3)-CH_2-O-CH_2-CH_3 + HI \xrightarrow{\text{heated}} ? Which of the following compounds will be formed?

A

CH3CH(CH3)CH2I+CH3CH2OHCH_3-CH(CH_3)-CH_2-I + CH_3CH_2OH

B

CH3CH(CH3)CH3+CH3CH2OHCH_3-CH(CH_3)-CH_3 + CH_3CH_2OH

C

CH3CH(CH3)CH2OH+CH3CH3CH_3-CH(CH_3)-CH_2OH + CH_3CH_3

D

CH3CH(CH3)CH2OH+CH3CH2ICH_3-CH(CH_3)-CH_2OH + CH_3-CH_2-I

Step-by-Step Solution

The reaction of an ether with hot concentrated HI involves the cleavage of the C-O bond. The mechanism depends on the nature of the alkyl groups attached to the oxygen.

  1. Mechanism Check: The ether is 1-ethoxy-2-methylpropane. The alkyl groups attached to the oxygen are ethyl (CH2CH3-CH_2CH_3) and isobutyl (CH2CH(CH3)2-CH_2CH(CH_3)_2). Both alkyl groups are primary.
  2. SN2 Pathway: When both alkyl groups are primary or secondary, the reaction proceeds via an SN2 mechanism involving the attack of the nucleophile (II^-) on the less sterically hindered carbon atom.
  3. Steric Hindrance: The ethyl group (CH3CH2CH_3CH_2-) is less sterically hindered than the isobutyl group ((CH3)2CHCH2(CH_3)_2CHCH_2-), which has branching at the β\beta-carbon.
  4. Product Formation: The iodide ion attacks the ethyl group to form ethyl iodide (CH3CH2ICH_3CH_2I). The proton (H+H^+) remains with the oxygen on the isobutyl group to form isobutyl alcohol ((CH3)2CHCH2OH(CH_3)_2CHCH_2OH).

Therefore, the products are Isobutyl alcohol and Ethyl iodide.

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 Ethersreactionchchchchochchxrightarrowtextheatedfollowingcompounds

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