Question

An alkene ‘A’ with molecular formula C9H10 on reductive ozonolysis gives two carbonyl

compounds ‘B’ and ‘C’. ‘B’ undergoes Cannizzaro reaction, where as ‘C’ undergoes aldol

condensation. When ‘B’ and ‘C’ are mixed and treated with dilute NaOH forms ‘D’ which

readily get dehydrated to form ‘E’. The trans isomer of ‘E’ is a main constituent of cinnamomum

zeylancium bark oil and used as flavoring agent in chewing gum, candy and beverages.

Identify A, B, C, D and E.​

Answer 1

Answer:

Compound B gives positive Fehling's test. It shows that it is an aldehyde and gives iodoform test which shows it has -COCH3 group. Compounds C is a ketone because it does not give Fehling's test but gives iodoform test which shows its also has -COCH3 groups.