[murendi]

Compound A, C9H16 was found to be optically active. On catalytic reduction over palladium catalyst, 2 equivalents of hydrogen were absorbed to yield compound B. Ozonolysis of compound A gave two compounds. One compound was identified as acetaldehyde, CH3CHO. The other compound C, was an optically active dialdehyde, C5H8O2. Formulate reactions and draw structures for compounds A, B and C. Plz help don't know how to work this out.

[Archer]

Ozonolysis of compound A gave two compounds. One compound was identified as acetaldehyde, CH3CHO.

Start by working out what functional group would give acetaldehyde by ozonolysis. There are two types of ozonolysis work up, which one is being used here?

[murendi]

I know that: A has 2 double bonds. Both of these will be cleaved by ozonolysis leaving carbonyl fragments. The five carbon dialdehyde has lost 4 carbons so one C5 unit must be produced together with two acetaldehydeunits Both A and C are optically active
A is CH3CH=CHCH(CH3)CH2CH=CHCH3
B is the saturated derivative
C is O=CHCH(CH3)CH2CH=O
But don't know what to do next.

[Archer]

I don't see anything wrong with what you have done so far.


Now go look up ozonolysis mechanisms online.