The major organic product in the reaction, CH3—O—CH(CH3)2+HI→Product is:
A
CH3OH+(CH3)2CHI
B
ICH3OCH(CH3)2
C
CH3OCl(CH3)2
D
CH3I+(CH3)2CHOH
Step-by-Step Solution
The reaction of an ether with hydrogen iodide (HI) involves the cleavage of the C-O bond.
Protonation: The first step is the protonation of the ether oxygen to form an oxonium ion: [CH3−OH+−CH(CH3)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 SN2 mechanism.
Nucleophilic Attack: In an SN2 reaction, the nucleophile (I−) attacks the less sterically hindered carbon atom . The methyl group (CH3−) is much less hindered than the isopropyl group (−CH(CH3)2).
Product Formation: The iodide ion attacks the methyl carbon, breaking the CH3−O bond. This results in the formation of methyl iodide (CH3I) and isopropyl alcohol ((CH3)2CHOH).
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