22.15The principal resonance forms of N-nitrosodimethylamine areAll atoms (except hydrogen) have octets of electrons in each of these structures. Other resonanceforms are less stable because they do not have a full complement of electrons around each atom.22.16Deamination of 1,1-dimethylpropylamine gives products that result from 1,1-dimethylpropylcation. Because 2,2-dimethylpropylamine gives the same products, it is likely that 1,1-dimethyl-propyl cation is formed from 2,2-dimethylpropylamine by way of its diazonium ion. A carbocationrearrangement is indicated.Once formed, 1,1-dimethylpropyl cation loses a proton to form an alkene or is captured by water togive an alcohol.22.17Phenols may be prepared by diazotization of the corresponding aniline derivative. The problemsimplifes itself, therefore, to the preparation of m-bromoaniline. Recognizing that arylamines are
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