The reaction of an ether with hot concentrated HI involves the cleavage of the C-O bond. The mechanism depends on the nature of the alkyl groups attached to the oxygen.
- Mechanism Check: The ether is 1-ethoxy-2-methylpropane. The alkyl groups attached to the oxygen are ethyl (−CH2CH3) and isobutyl (−CH2CH(CH3)2). Both alkyl groups are primary.
- SN2 Pathway: When both alkyl groups are primary or secondary, the reaction proceeds via an SN2 mechanism involving the attack of the nucleophile (I−) on the less sterically hindered carbon atom.
- Steric Hindrance: The ethyl group (CH3CH2−) is less sterically hindered than the isobutyl group ((CH3)2CHCH2−), which has branching at the β-carbon.
- Product Formation: The iodide ion attacks the ethyl group to form ethyl iodide (CH3CH2I). The proton (H+) remains with the oxygen on the isobutyl group to form isobutyl alcohol ((CH3)2CHCH2OH).
Therefore, the products are Isobutyl alcohol and Ethyl iodide.