Give the major products that are formed by heating each of the following ethers with $HI$.
$(i)$ $CH_3-CH_2-CH(CH_3)-CH_2-O-CH_2-CH_3$
$(ii)$ $CH_3-CH_2-CH_2-O-C(CH_3)_2-CH_2-CH_3$
$(iii)$ $C_6H_5-CH_2-O-C_6H_5$
$(i)$ $CH_3-CH_2-CH(CH_3)-CH_2-O-CH_2-CH_3$
$(ii)$ $CH_3-CH_2-CH_2-O-C(CH_3)_2-CH_2-CH_3$
$(iii)$ $C_6H_5-CH_2-O-C_6H_5$
(N/A) $(i)$ The reaction follows $S_N2$ mechanism because the alkyl groups are primary. The smaller alkyl group forms the alkyl iodide. Products: $CH_3-CH_2-CH(CH_3)-CH_2OH + CH_3CH_2I$.
$(ii)$ The reaction follows $S_N1$ mechanism because the ether contains a tertiary alkyl group. The tertiary carbocation is more stable. Products: $CH_3CH_2CH_2OH + CH_3CH_2-C(CH_3)_2I$.
$(iii)$ The cleavage occurs at the $C-O$ bond where the benzyl carbocation is formed,which is resonance stabilized. Products: $C_6H_5CH_2I + C_6H_5OH$.
$(ii)$ The reaction follows $S_N1$ mechanism because the ether contains a tertiary alkyl group. The tertiary carbocation is more stable. Products: $CH_3CH_2CH_2OH + CH_3CH_2-C(CH_3)_2I$.
$(iii)$ The cleavage occurs at the $C-O$ bond where the benzyl carbocation is formed,which is resonance stabilized. Products: $C_6H_5CH_2I + C_6H_5OH$.
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Similar Questions
The products formed when diethyl ether is reacted with cold $HI$ are
Which of the following compounds is formed when ether is dissolved in cold concentrated sulphuric acid?
What are $A$ and $B$ in the following reaction?
$CH_3-CH_2-CH_2-O-C(CH_3)_2-CH_2-CH_3 \xrightarrow{HI} A + B$
$CH_3-CH_2-CH_2-O-C(CH_3)_2-CH_2-CH_3 \xrightarrow{HI} A + B$
The following are possible syntheses of phenyl propyl ether. Which one would work?
$(i)$ $C_6H_5OH$ $\xrightarrow{KNH_2}$ $\xrightarrow{CH_3CH_2CH_2Br}$
(ii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaOH}$ $\xrightarrow{C_6H_5Br}$
(iii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaH}$ $\xrightarrow{C_6H_5Br}$
$(i)$ $C_6H_5OH$ $\xrightarrow{KNH_2}$ $\xrightarrow{CH_3CH_2CH_2Br}$
(ii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaOH}$ $\xrightarrow{C_6H_5Br}$
(iii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaH}$ $\xrightarrow{C_6H_5Br}$
Medium
View SolutionThe oxygen atom in an ether is:
Medium
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