2001 AIPMT HydrocarbonsOzonolysis of Alkenes Easy Question 2 of 2 in Ozonolysis of Alkenes

Which alkene on ozonolysis gives $CH_3CH_2CHO$ and $CH_3COCH_3$ : -

A $CH_3CH_2CH=C(CH_3)_2$
B $CH_3CH_2CH=CHCH_2CH_3$
C $CH_3CH_2CH=CHCH_3$
D $(CH_3)_2C=CHCH_3$

The answer is A.

Solution

In ozonolysis, the C=C double bond is cleaved and each carbon of the double bond becomes a C=O group.
To find the alkene, remove the oxygen atoms from the two carbonyl compounds and join the two carbonyl carbons by a double bond.
$CH_3CH_2CH=O$ + $O=C(CH_3)_2$ $\Rightarrow$ $CH_3CH_2CH=C(CH_3)_2$ (2-methylpent-2-ene)
Check: $CH_3CH_2CH=C(CH_3)_2 \xrightarrow{(i)\ O_3\ (ii)\ Zn/H_2O} CH_3CH_2CHO + CH_3COCH_3$
So the alkene is $CH_3CH_2CH=C(CH_3)_2$.

Concept Working backward from ozonolysis products

Ozonolysis of Alkenes in past papers

2 questions from this chapter have appeared across 2 exam years.