Give an explanation for each of the following facts. (a) The barrier to internal

Chapter 23, Problem 23.59

(choose chapter or problem)

Give an explanation for each of the following facts. (a) The barrier to internal rotation about the N-phenyl bond in N-methyl-p-nitroaniline is considerably higher (4246 kJ mol1 , or 1011 kcal mol1 ) than that in N-methylaniline itself (about 25 kJ mol1 , or 6 kcal mol1 ). (b) Cis- and trans-1,3-dimethylpyrrolidine rapidly interconvert. (c) CH3NHCH2NHCH3 is unstable in aqueous solution. (d) The following compound exists as the enamine isomer shown rather than as an imine: (e) Diazotization of 2,4-cyclopentadien-1-amine gives a diazonium salt, which, unlike most aliphatic diazonium ions, is relatively stable and does not decompose to a carbocation.

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