Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.
Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.
Solution and Explanation
The reaction of Williamson synthesis involves SN2 attack of an alkoxide ion on a primary alkyl halide. But if secondary or tertiary alkyl halides are taken in place of primary alkyl halides, then elimination would compete over substitution. As a result, alkenes would be produced. This is because alkoxides are nucleophiles as well as strong bases. Hence, they react with alkyl halides, which results in an elimination reaction.
Top Questions on Alcohols, Phenols And Ethers
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Concepts Used:
Classification - Alcohols, Phenols and Ethers
Alcohols, phenols, and ethers are organic compounds that can be classified based on their molecular structure and functional groups.
Classification of Alcohols:
- Alcohols can be classified as primary, secondary, or tertiary, based on the number of alkyl groups attached to the carbon atom bearing the hydroxyl group.
- Primary alcohols have one alkyl group attached to the carbon, secondary alcohols have two, and tertiary alcohols have three.
Classification of Phenols:
- Phenols can be classified based on the number and position of the hydroxyl groups attached to the aromatic ring.
- Monohydroxy phenols have one hydroxyl group, while dihydroxy phenols have two.
- Polyhydroxy phenols have more than two hydroxyl groups.
- Resorcinol and catechol are examples of dihydroxy phenols, while tannins are examples of polyhydroxy phenols.
Classification of Ethers:
- Ethers can be classified based on the nature of the alkyl or aryl groups attached to the oxygen atom.
- Simple ethers have two alkyl or aryl groups, while mixed ethers have one alkyl and one aryl group.
- Crown ethers are cyclic ethers that contain multiple ether groups and are used as complexing agents.
In summary, alcohols, phenols, and ethers can be classified based on their molecular structure and functional groups. Understanding the classification of these compounds is important for predicting their reactivity and understanding their potential applications in various fields, including chemistry, biology, and industry.