Illustrate with examples the limitations of Williamson synthesis for the preparation of certain type of ethers.

Solution

Williamson synthesisinvolves S_N2 attack may an alkoxide ion on primary alkyl halide. Better result are obtained if the alkyl halides is primary. In case of secondary and tertiary alkyl halide, elimination competes over substitution.
(i) If the alkyl halide is tertiary, then the major product is an alkene and alkoxide then acts as a strong base not as a nucelophile.
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(ii) Chlorobenzene does not give Williamson’s synthesis due to partial double bond character of C—Cl bond. So, aromatic ether are prepared from sodium phenoxide.

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Some More Questions From Alcohols, Phenols and Ethers Chapter

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Alcohols, Phenols And Ethers

Illustrate with examples the limitations of Williamson synthesis for the preparation of certain type of ethers.

Some More Questions From Alcohols, Phenols and Ethers Chapter

Classify the following as primary, secondary and tertiary alcohols:

Classify the following as primary, secondary and tertiary alcohols:

Classify the following as primary, secondary and tertiary alcohols:

Identify allylic alcohols in the above examples.

Name the following compounds according to IUPAC system.

Name the following compounds according to IUPAC system.

Name the following compounds according to IUPAC system.

Name the following compounds according to IUPAC system.

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