Dolbier HW Solutions 518

Dolbier HW Solutions 518 - 612 AMINES 22.15 The principal...

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22.15 The principal resonance forms of N -nitrosodimethylamine are All atoms (except hydrogen) have octets of electrons in each of these structures. Other resonance forms are less stable because they do not have a full complement of electrons around each atom. 22.16 Deamination of 1,1-dimethylpropylamine gives products that result from 1,1-dimethylpropyl cation. 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 carbocation rearrangement is indicated. Once formed, 1,1-dimethylpropyl cation loses a proton to form an alkene or is captured by water to give an alcohol. 22.17 Phenols may be prepared by diazotization of the corresponding aniline derivative. The problem simpli f es itself, therefore, to the preparation of m -bromoaniline. Recognizing that arylamines are
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