The major organic product in the reaction, CH3—O—CH(CH3)2+HI→Product is:
A
CH3OH+(CH3)2CHI
B
ICH2OCH(CH3)2
C
CH3OC(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 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 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 (only 3 H atoms) than the isopropyl group (−CH(CH3)2, which has two methyl groups creating steric bulk).
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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