Which of the following products are formed when $\mathrm{cyclohexene}$ undergoes ozonolysis followed by reductive workup with ${\mathrm{Zn}}_{H}O$?

• A. Cyclohexanone
• B. $O_2$ and ${\mathrm{CO}}_2$
• C. Adipic acid
• D. Hexane-1,6-dial (a dialdehyde)

Answer: (D)

Verified step by step guidance

1. Identify the structure of cyclohexene: it is a six-membered ring containing one double bond between two carbon atoms.
2. Recall that ozonolysis cleaves double bonds by breaking the C=C bond and forming carbonyl compounds at the cleavage sites.
3. Write the general ozonolysis reaction for an alkene followed by reductive workup (using Zn/H2O), which converts the ozonide intermediate into aldehydes or ketones without further oxidation:
4. \[ \text{Alkene} \xrightarrow{O_3} \text{Ozonide} \xrightarrow{Zn/H_2O} \text{Aldehydes or Ketones} \]
5. Apply this to cyclohexene: the double bond is cleaved, opening the ring and producing two aldehyde groups at the carbons where the double bond was, resulting in hexane-1,6-dial (a dialdehyde).
6. Confirm that no further oxidation occurs under reductive workup conditions, so products like adipic acid (a dicarboxylic acid) or CO2 and O2 are not formed.