Chapter 109 of 2362 min read

Isomerism: structural and stereo

Why this is asked: Cis/trans and E/Z don't always agree — E/Z is assigned by CIP priority, cis/trans by which groups simply look alike, so a compound can be "cis" by eye but "E" by priority. Meso compounds are the other classic trap: chiral centres present, but an internal plane of symmetry cancels the optical rotation, so 2ⁿ overcounts the stereoisomers whenever a meso form exists — tartaric acid is the standard example.

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Test yourself

•Which one of the following compounds can exist as cis–trans isomers?
•The total number of possible isomers (both structural as well as stereoisomers) of cyclic ethers of molecular formula $C_{4} H_{8} O$ is:

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