back to directory
NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

The major organic product in the reaction, CH3OCH(CH3)2+HIProductCH_3 — O — CH(CH_3)_2 + HI \rightarrow \text{Product} is:

A

CH3OH+(CH3)2CHICH_3OH + (CH_3)_2CHI

B

ICH2OCH(CH3)2ICH_2OCH(CH_3)_2

C

CH3OC(CH3)2CH_3OC(CH_3)_2

D

CH3I+(CH3)2CHOHCH_3I + (CH_3)_2CHOH

Step-by-Step Solution

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

  1. Protonation: The first step is the protonation of the ether oxygen to form an oxonium ion: [CH3OH+CH(CH3)2][CH_3-OH^+-CH(CH_3)_2].
  2. Mechanism Selection: The reaction pathway depends on the nature of the alkyl groups. Neither group is tertiary (methyl is primary, isopropyl is secondary), so the reaction generally follows an SN2S_N2 mechanism.
  3. Nucleophilic Attack: In an SN2S_N2 reaction, the nucleophile (II^-) attacks the less sterically hindered carbon atom. The methyl group (CH3CH_3-) is much less hindered (only 3 H atoms) than the isopropyl group (CH(CH3)2-CH(CH_3)_2, which has two methyl groups creating steric bulk).
  4. Product Formation: The iodide ion attacks the methyl carbon, breaking the CH3OCH_3-O bond. This results in the formation of methyl iodide (CH3ICH_3I) and isopropyl alcohol ((CH3)2CHOH(CH_3)_2CHOH).

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 Ethersorganicproductreactionrightarrowtextproduct

More Alcohols, Phenols and Ethers Questions

View all

This neet chemistry practice question is part of the TopperSquare free question bank. TopperSquare offers 15,000+ chapter-wise NEET MCQs across Physics, Chemistry, and Biology with detailed step-by-step explanations, full mock tests, NEET PYQs (2010–2024), and an AI-powered performance analytics dashboard. browse all neet practice questions → · practice chemistry sets →