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Before Modern Spectroscopic Methods Were Developed,structures of Many Complex Amines

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Before modern spectroscopic methods were developed,structures of many complex amines were elucidated by examining the products obtained during Hofmann elimination of their quaternary ammonium hydroxides.The typical procedure involved the following steps,repeated as necessary,depending on whether the amine was primary,secondary or tertiary,until the final product was nitrogen-free: i)CH3I (excess); ii)Ag2O,H2O; iii)heat.What product(s)is (are)likely to be formed if 3,4-dimethylpiperidine is subjected to the above procedure?

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The reaction sequence would need to be r...

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