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Chapter 25: Carbohydrates
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Alkylation of Carbohydrates
Reaction type: Nucleophilic Substitution (SN2)
Summary
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The -OH groups in carbohydrates react
readily with alkylating agents to give ethers via a simple SN2
reaction.
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Methylation can be achieved using methyl iodide, CH3I, and silver
oxide Ag2O.
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Benzylation can be achieved using benzyl halides (Cl, Br, I), C6H5CH2X
and a base such as NaH or Ag2O.
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These reactions are often used in carbohydrate chemistry since the products
act as protecting groups for the
reactive -OH functional group.
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The -OR group at the acetal center can be converted back
to an -OH with aqueous acid.
Related Reactions