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The reaction: CH3CH(CH3)CH2OCH2CH3+HIheated?CH_3-CH(CH_3)-CH_2-O-CH_2-CH_3 + HI \xrightarrow{\text{heated}} ? Which of the following compounds will be formed?

A

CH3CH(CH3)CH2I+CH3CH2OHCH_3-CH(CH_3)-CH_2-I + CH_3CH_2OH

B

CH3CH(CH3)CH3+CH3CH2OHCH_3-CH(CH_3)-CH_3 + CH_3CH_2OH

C

CH3CH(CH3)CH2OH+CH3CH3CH_3-CH(CH_3)-CH_2OH + CH_3CH_3

D

CH3CH(CH3)CH2OH+CH3CH2ICH_3-CH(CH_3)-CH_2OH + CH_3-CH_2-I

Step-by-Step Solution

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.

  1. Mechanism Check: The ether is 1-ethoxy-2-methylpropane. The alkyl groups attached to the oxygen are ethyl (CH2CH3-CH_2CH_3) and isobutyl (CH2CH(CH3)2-CH_2CH(CH_3)_2). Both alkyl groups are primary.
  2. SN2 Pathway: When both alkyl groups are primary or secondary, the reaction proceeds via an SN2 mechanism involving the attack of the nucleophile (II^-) on the less sterically hindered carbon atom.
  3. Steric Hindrance: The ethyl group (CH3CH2CH_3CH_2-) is less sterically hindered than the isobutyl group ((CH3)2CHCH2(CH_3)_2CHCH_2-), which has branching at the β\beta-carbon.
  4. Product Formation: The iodide ion attacks the ethyl group to form ethyl iodide (CH3CH2ICH_3CH_2I). The proton (H+H^+) remains with the oxygen on the isobutyl group to form isobutyl alcohol ((CH3)2CHCH2OH(CH_3)_2CHCH_2OH).

Therefore, the products are Isobutyl alcohol and Ethyl iodide.

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