Para-nitrosation of N,N-dimethylaniline (C-nitrosation) is believed to take place through an electrophilic attack by N+O ions. (a)

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Para-nitrosation of N,N-dimethylaniline (C-nitrosation) is believed to take place through an electrophilic attack by N+O ions.

(a) Show how N+O ions might be formed in an aqueous solution of NaNO2 and HCl.

(b) Write a mechanism for p-nitrosation of N,N-dimethylaniline.

(c) Tertiary aromatic amines and phenols undergo C-nitrosation reactions, whereas most other benzene derivatives do not. How can you account for this difference?

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Organic Chemistry

ISBN: 978-1118133576

11th edition

Authors: Graham Solomons, Craig Fryhle, Scott Snyder

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