Numerical answer
The compound (hepta-2,5-dien-4-ol) is considered with all its possible configurational stereoisomers, counting enantiomers and diastereomers separately. The total number of distinct stereoisomers is ______.
Show answer and solution
Answer: 4
There are two bonds, each of which can be or , and one carbinol carbon, , carrying , and two propenyl arms. Take the combinations of double-bond geometry. In the and isomers the two arms at are identical, so is not stereogenic and each molecule is achiral with a mirror plane. This gives 1 isomer each, so 2 in total. In the combination one arm is an -propenyl and the other a -propenyl group. These arms are diastereomorphic (not mirror images), so carries four different groups and is a genuine stereocentre; by the CIP rule it can be or . The molecule has no mirror plane, so it exists as a pair of enantiomers, and . The combination is the same molecule as read from the other end, so it adds nothing new. Total .
Saved on this device. Sign in or create a free account to keep it on every device.