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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

The major products C and D formed in the following reaction respectively are: CH3CH2CH2OC(CH3)3+Excess HIΔC+DCH_3CH_2CH_2-O-C(CH_3)_3 + \text{Excess } HI \xrightarrow{\Delta} C + D

A

H3CCH2CH2IH_3C-CH_2-CH_2-I and IC(CH3)3I-C(CH_3)_3

B

H3CCH2CH2OHH_3C-CH_2-CH_2-OH and IC(CH3)3I-C(CH_3)_3

C

H3CCH2CH2IH_3C-CH_2-CH_2-I and HOC(CH3)3HO-C(CH_3)_3

D

H3CCH2CH2OHH_3C-CH_2-CH_2-OH and HOC(CH3)3HO-C(CH_3)_3

Step-by-Step Solution

The reaction of an ether with hydrogen iodide (HI) involves the cleavage of the C-O bond.

  1. Mechanism (First Cleavage): The ether contains a primary propyl group and a tertiary butyl group. When one of the alkyl groups is tertiary, the reaction proceeds via an SN1S_N1 mechanism due to the stability of the tertiary carbocation . Protonation of the oxygen is followed by the cleavage of the bond between oxygen and the tertiary carbon, forming the stable tert-butyl carbocation and propyl alcohol. The iodide ion attacks the carbocation to form tert-butyl iodide (IC(CH3)3I-C(CH_3)_3).
  2. Effect of Excess HI: The reaction mixture contains Excess HI. The alcohol formed in the first step (propyl alcohol, H3CCH2CH2OHH_3C-CH_2-CH_2-OH) reacts further with HI. The hydroxyl group is replaced by iodine via nucleophilic substitution : ROH+HIRI+H2OR-OH + HI \rightarrow R-I + H_2O. This converts propyl alcohol to propyl iodide (H3CCH2CH2IH_3C-CH_2-CH_2-I).
  3. Conclusion: Both alkyl groups are converted to their corresponding iodides.

Products: H3CCH2CH2IH_3C-CH_2-CH_2-I + IC(CH3)3I-C(CH_3)_3

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 Ethersproductsformedfollowingreactionrespectively

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