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The configurations of the double bonds in the following molecule are :

A dienoic acid: CO2H-CH=CH- attached to a tetrasubstituted alkene carrying two cyclobutyl groups and a phenyl group

  • A.2E, 4E
  • B.2E, 4Z
  • C.2Z, 4E
  • D.2Z, 4Z

Answer: B

The configurations are 2E, 4Z.

Number the chain from the carboxyl carbon (C-1). At the C-2=C-3 double bond, the carboxyl group on C-2 and the rest of the chain on C-3 lie on opposite sides of the bond as drawn, so it is E.

At C-4=C-5, compare the substituents by CIP priority. On C-4: the cyclobutyl carbon (C, C, H) versus C-3 of the chain (C, C, H with a duplicated carbon); at the next sphere the chain wins because its branch leads to C-2 bearing (C, C, H), while the ring branch leads only to CH2 groups. On C-5: phenyl (C, C, C) beats cyclobutyl (C, C, H). The higher-priority groups, the C-3 chain and the phenyl, are on the same side of the double bond, so it is Z.

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