(a) In 1884 Perkin achieved a successful synthesis of cyclopropanecarboxylic acid from sodiomalonic ester and 1, 2-dibromoethane. Outline the reactions involved in this synthesis.
(b) In 1885 Perkin synthesized five-membered carbocyclic compounds D and E in the following way:

where D and E are diastereomers; D can be resolved into enantiomeric forms while E cannot. What are the structures of A-E?
(c) Ten years later Perkin was able to synthesize 1, 4-dibromobutane; he later used this compound and diethyl malonate to prepare cyclopentanecarboxylic acid. Show the reactions involved.

Transcribed Image Text:

O C 2 EtONa Br OEtB Na Et heat, D (C,HiooE CHio0,) (1) HO H.o