?Compounds that contain a carbon–nitrogen double bond are capable of stereoisomerism

Chapter 18, Problem 18.26

(choose chapter or problem)

Compounds that contain a carbon–nitrogen double bond are capable of stereoisomerism much like that seen in alkenes. The structures

are stereoisomeric. Specifying stereochemistry in these systems is best done by using E–Z descriptors and considering the nitrogen lone pair to be the lowest priority group. Write the structures, clearly showing stereochemistry, of the following:

(a) (Z)-CH3CH=NCH3

(b) (E)-Acetaldehyde oxime

(c) (Z)-2-Butanone hydrazone

(d) (E)-Acetophenone semicarbazone

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