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Acid catalysis is not necessary for this step the

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Unformatted text preview: aldehyde, formaldehyde (methanal CH2=O). NH CH2=O N NHMe CH2 H Me N CH2=O N Me NHMe Purpose of the problem Extension of simple acetal chemistry into related reactions with nitrogen. Suggested solution Both reactions start in the same way by attack of a nitrogen nucleophile on formaldehyde. Acid catalysis is not necessary for this step. The first reaction ends with the formation of the iminium ion by acid- catalysed dehydration. NH CH2 O O N N OH H N OH2 H Me as above NHMe CH2 In the other reaction a second amino group is waiting to capture the iminium ion by cyclisation to form a stable five- membered ring. NHMe iminium formed N N CH2 NHMe Me N N Me 3 4 Solutions Manual to accompany Organic Chemistry 2e PROBLEM 4 In the textbook (p. 104) we showed you a selective hydrolysis of an...
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