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NEET CHEMISTRYMedium

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

ICH3OCH(CH3)2ICH_3OCH(CH_3)_2

C

CH3OCl(CH3)2CH_3OCl(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 pathway depends on the nature of the alkyl groups. Neither group is tertiary (methyl is primary, isopropyl is secondary), so the reaction 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 than the isopropyl group (CH(CH3)2-CH(CH_3)_2).
  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).
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