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 $CH_3CH_2CH=C(CH_3)_2$.
ConceptWorking backward from ozonolysis products
Ozonolysis of Alkenes in past papers
2 questions from this chapter have appeared across 2 exam years.