)
on ozonolysis gives a mixture of two compounds 'B' and 'C? Compound 'B' gives
positive Fehling's test and also forms iodo form on treatment with 
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:
(i)
Since compound 'B' gives Fehling's test, therefore, it must be aldehyde.
Further since aldehyde 'B' gives iodoform on treatment with 
and NaOH, therefore, 'B'
must be acetaldehyde 
.
(ii) Since alkene 'A' (MP
) contains five carbon
atoms and one of the products of ozonolysis is ?B? which contains two carbon
atoms, therefore, the other product of ozonolys is, i.e., 'C' must contain three
carbon atoms,
(iii) Since compound 'C' does not give Fehling's test, it must be
a ketone. Further since ketone 'C' contain three carbon atoms and gives
iodoform on treatment with and
NaOH, therefore, ketone 'C' must be acetone
(iv) Write the products of ozonolysis, i.e., 'B' and 'C' 
side by side with their
C = O groups facing each other. Remove the oxygen atoms and join the remaining
fragments by a doubles bond, the structure of alkene 'A' is
2-methylbut-2-ene.
(v) Formation of iodoform from 'B' and 'C' may be
explained as follows :
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