Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.
(N/A) The Williamson synthesis involves the $S_{N}2$ attack of an alkoxide ion on a primary alkyl halide.
For example: $(CH_3)_3CONa + CH_3Cl \rightarrow (CH_3)_3COCH_3 + NaCl$
However,if secondary or tertiary alkyl halides are used instead of primary alkyl halides,elimination competes with substitution.
As a result,alkenes are produced instead of ethers because alkoxides act as both nucleophiles and strong bases.
For example: $(CH_3)_3CCl + NaOCH_3 \rightarrow CH_3-C(CH_3)=CH_2 + CH_3OH + NaCl$
For example: $(CH_3)_3CONa + CH_3Cl \rightarrow (CH_3)_3COCH_3 + NaCl$
However,if secondary or tertiary alkyl halides are used instead of primary alkyl halides,elimination competes with substitution.
As a result,alkenes are produced instead of ethers because alkoxides act as both nucleophiles and strong bases.
For example: $(CH_3)_3CCl + NaOCH_3 \rightarrow CH_3-C(CH_3)=CH_2 + CH_3OH + NaCl$
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Similar Questions
The products formed in the following reaction are $C_6H_5-OCH_3 + HI \xrightarrow{\text{heat}}$
MediumIIT 1995
View SolutionConsider the following reaction.
$C_6H_5-O-CH_2-C_6H_5 + HI \rightarrow \text{Product}$
Statement $I$ : In the above reaction, the product formed will be a mixture of benzyl alcohol and iodobenzene.
Statement $II$ : In the above reaction, the $-O-CH_2-$ bond is cleaved to give the product.
In the light of the above statements, choose the correct answer from the options given below:
$C_6H_5-O-CH_2-C_6H_5 + HI \rightarrow \text{Product}$
Statement $I$ : In the above reaction, the product formed will be a mixture of benzyl alcohol and iodobenzene.
Statement $II$ : In the above reaction, the $-O-CH_2-$ bond is cleaved to give the product.
In the light of the above statements, choose the correct answer from the options given below:
Predict the major product for the following reaction:
$m-CH_3O-C_6H_4-CH_2CH_2-O-CH(CH_3)Ph \xrightarrow{HI (excess), \text{heat}} ?$
$m-CH_3O-C_6H_4-CH_2CH_2-O-CH(CH_3)Ph \xrightarrow{HI (excess), \text{heat}} ?$
Difficult
View SolutionGiven below are two statements: one is labelled as Assertion $(A)$ and the other is labelled as Reason $(R).$
Assertion $(A):$ Synthesis of ethyl phenyl ether may be achieved by Williamson synthesis.
Reason $(R):$ Reaction of bromobenzene with sodium ethoxide yields ethyl phenyl ether.
In the light of the above statements,choose the most appropriate answer from the options given below:
Assertion $(A):$ Synthesis of ethyl phenyl ether may be achieved by Williamson synthesis.
Reason $(R):$ Reaction of bromobenzene with sodium ethoxide yields ethyl phenyl ether.
In the light of the above statements,choose the most appropriate answer from the options given below:
For the reaction: $CH_3-CH(CH_3)-O-CH_3 + HI \rightarrow X + Y$,identify $X$ and $Y$.
Medium
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