Provide a reasonable explanation for each of the following observations:
(a) 4-Methylpiperidine has a higher boiling point than N-methylpiperidine.

(b) Two isomeric quaternary ammonium salts are formed in comparable amounts when 4- tert-butyl-N-methylpiperidine is treated with benzyl chloride. (Building a molecular model will help.)

(c) When tetramethylammonium hydroxide is heated at 130°C, trimethylamine and methanol are formed.
(d) The major product formed on treatment of 1-propanamine with sodium nitrite in dilute hydrochloric acid is 2-propanol.

Transcribed Image Text:

70«О HN CH3 CH,N 4-Methylpiperidine N-Methylpiperidine (bp 129°C) (bp 106 C) CH N C(CH3)3 4-tert-Butyl-N-methylpiperidine