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Organic Chemistry

Why acetanilide is more para directing than aniline in bromination?


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August 06, 2008 1:53AM

The -NHCOR group is less powerfully activating then the -NH2 group. In addition, the degree of steric hindrance is much greater in the case of a -NHCOR group, such as is found in acetanilide. This results in the compound being much more para directing. For an example, see Morrison and Boyd 's text "Organic Chemistry", sixth edition, Page 848.