Question

An alkene ‘A’ (Mol. formula $C_5{H}_{1}0)$ on ozonolysis gives a mixture of two compounds ‘B’ and ‘C’. Compound ‘B’ gives positive Fehling’s test and also forms iodoform on treatment with $I_2$ and$NaOH.$ Compound ‘C’ does not give Fehling’s test but forms iodoform. Identify the compounds A, B and C. Write the reaction for ozonolysis and formation of iodoform from B and C.

Answer 1

Identifying A, B and C

The described ozonolysis reaction is:


$B\to$ Gives positive Fehling’s test and iodoform test on treatment with $I_2$and $NaOH.$
$C\to$ Does not give Fehling’s test but forms iodoform.
Compound B gives positive Fehling’s test, this shows that it is an aldehyde, and it gives iodoform test which signifies that it has $-COC{H}_3$ group as well.

Thus, structure of B


Compound C does not give Fehling’s test which signifies that it is a ketone and since it gives iodoform test thus it has $-COC{H}_3$ group.