Reductive ozonolysis (O$_3$, then Zn/H$_2$O) of $2$-methylbut-$2$-ene gives:
ATwo molecules of propanaldehyde
BAcetaldehyde + propanaldehyde
CTwo molecules of acetone
DAcetone + acetaldehyde
Answer & Solution
Correct answer: D. Acetone + acetaldehyde
2-methylbut-2-ene is $\mathrm{(CH_3)_2C=CH-CH_3}$. Ozonolysis cleaves the C=C
giving two carbonyl fragments — one from each side of the original double bond.
Left fragment $(CH_3)_2C{=}O$
→ **acetone** (a ketone, since that carbon had two methyl groups).
Right fragment $CH_3-CH{=}O$
→ **acetaldehyde** (an aldehyde, since that carbon had one H).
Reductive workup (Zn/H₂O) is what preserves the aldehyde
oxidative workup (H₂O₂) would over-oxidise it to a carboxylic acid.
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