Which of the following sets of products is formed when $1-\text{butene}$ undergoes ozonolysis followed by reductive workup ($\text{Zn}/\text{AcOH}$)?

• A. $\text{butanone}$ and $\text{carbon} \text{dioxide}$
• B. $\text{ethanal}$ and $\text{ethanal}$
• C. $\text{acetic} \text{acid}$ and $\text{acetaldehyde}$
• D. $\text{propanal}$ and $\text{formaldehyde}$

Answer: (D)

Verified step by step guidance

1. Identify the structure of 1-butene. It is an alkene with the double bond between the first and second carbon atoms: CH2=CH-CH2-CH3.
2. Recall that ozonolysis cleaves the carbon-carbon double bond and forms carbonyl compounds (aldehydes or ketones) at the site of the double bond.
3. Write the cleavage of the double bond in 1-butene: the bond between C1 and C2 breaks, resulting in two fragments. The first fragment is the carbon at C1 with its substituents, and the second fragment is the carbon at C2 with the rest of the chain.
4. Determine the products formed from each fragment after reductive workup (using Zn/AcOH), which converts ozonides into aldehydes or ketones without further oxidation.
5. Assign the products: the fragment from C1 becomes formaldehyde (HCHO) because it is a terminal CH2 group, and the fragment from C2 to C4 becomes propanal (CH3CH2CHO), an aldehyde with three carbons.