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
Anisole can be prepared by the action of methyl iodide on sodium phenate. The reaction is called:
MediumKCET 2008
View SolutionWhat is the product of the reaction between $CH_3ONa$ and $CH_3CH_2Br$?
$CH_3ONa + CH_3CH_2Br \rightarrow$ ?
$CH_3ONa + CH_3CH_2Br \rightarrow$ ?
Give the common and $\rm {IUPAC}$ names for the following ether compounds:
$(i) \ CH_3OCH_3$
$(ii) \ C_2H_5OC_2H_5$
$(iii) \ C_6H_5OC_6H_5$
$(iv) \ CH_3OCH_2CH_2CH_3$
$(v) \ CH_3OCH(CH_3)_2$
$(vi) \ C_6H_5OCH_3$
$(vii) \ C_6H_5OCH_2CH_3$
$(viii) \ C_6H_5O(CH_2)_6CH_3$
$(ix) \ C_6H_5OCH_2CH_2CH(CH_3)_2$
$(x) \ CH_3OCH_2CH_2OCH_3$
$(xi) \ C_2H_5OCH_2CH_2OC_2H_5$
$(xii) \ CH_3OCH_2CH_2CH_2OCH_3$
$(xiii) \ CH_3OCH_2CH_2OC_2H_5$
$(xiv) \ \text{Cyclohexyl methyl ether}$
$(i) \ CH_3OCH_3$
$(ii) \ C_2H_5OC_2H_5$
$(iii) \ C_6H_5OC_6H_5$
$(iv) \ CH_3OCH_2CH_2CH_3$
$(v) \ CH_3OCH(CH_3)_2$
$(vi) \ C_6H_5OCH_3$
$(vii) \ C_6H_5OCH_2CH_3$
$(viii) \ C_6H_5O(CH_2)_6CH_3$
$(ix) \ C_6H_5OCH_2CH_2CH(CH_3)_2$
$(x) \ CH_3OCH_2CH_2OCH_3$
$(xi) \ C_2H_5OCH_2CH_2OC_2H_5$
$(xii) \ CH_3OCH_2CH_2CH_2OCH_3$
$(xiii) \ CH_3OCH_2CH_2OC_2H_5$
$(xiv) \ \text{Cyclohexyl methyl ether}$
Medium
View Solution$C_2H_5-Br + CH_3ONa \to A \xrightarrow[{(cold)}]{{HI}} B,$ product $B$ is
Difficult
View SolutionEtherates are:
Difficult
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