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## Q. 7.1

assigning E and Z Configurations to Substituted alkenes

Assign E or Z configuration to the double bond in the following compound:

S t r a t e g y
Look at the two substituents connected to each double-bond carbon, and determine their ranking using the Cahn–Ingold–Prelog rules. Then see whether the two higher-ranked groups are on the same or opposite sides of the double bond.

## Verified Solution

The left-hand carbon has –H and $–CH_3$ substituents, of which $–CH_3$ ranks higher by sequence rule 1. The right-hand carbon has $–CH(CH_3)_2$ and $–CH_2OH$ substituents, which are equivalent by rule 1. By rule 2, however, $–CH_2OH$ ranks higher than $–CH(CH_3)_2$ because the substituent $–CH_2OH$ has an oxygen
as its highest second atom, but $–CH(CH_3)_2$ has a carbon as its highest second atom. The two higher-ranked groups are on the same side of the double bond, so we assign Z configuration.