Most amides are reduced to amines with lithium aluminum hydride (Section 21.9); however
Chapter 21, Problem 21.41(choose chapter or problem)
Most amides are reduced to amines with lithium aluminum hydride (Section 21.9); however, N-methoxy-N-methylamides are an exception. The initial reduction product is a cyclic intermediate that is hydrolyzed to an aldehyde on workup. H O N O AlH2 O N O CH3 O CH3 CH3 H3O+ LiAlH4 N-Methoxy-Nmethylcyclohexanecarboxamide N-methoxy-N-methylamides are readily synthesized from carboxylic acids, by reaction ofthe acyl chloride with N,O-dimethylhydroxylamine (CH3ONHCH3).(a) How many equivalents of LiAlH4 are required for the reduction of the amide?(b) Write a series of equations to show the preparation of cyclohexanecarbaldehyde fromthe appropriate carboxylic acid and any other necessary reagents.(c) Would you expect the amide shown here to undergo reduction with lithium aluminumhydride to give the same product? Why or why not?
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