Which of the following products could be produced by oxidative cleavage of an $\mathrm{alkyne}$?

• A. $\mathrm{Alkanes}$
• B. $\mathrm{Alcohols}$
• C. $\mathrm{Aldehydes}$
• D. $\mathrm{Carboxylic} \mathrm{acids}$

Answer: (D)

Verified step by step guidance

1. Understand that oxidative cleavage of an alkyne involves breaking the triple bond completely, typically using strong oxidizing agents like potassium permanganate (KMnO\_4) or ozone (O\_3) followed by oxidative workup.
2. Recall that when an alkyne undergoes oxidative cleavage, each carbon of the triple bond is converted into a carboxylic acid group if it is bonded to at least one hydrogen; if the carbon is terminal (bonded to a hydrogen), it forms carbon dioxide instead.
3. Recognize that alkanes and alcohols are not typical products of oxidative cleavage because the process involves breaking bonds and adding oxygen, which leads to oxidation rather than reduction or simple substitution.
4. Note that aldehydes are generally not stable products of alkyne oxidative cleavage because the oxidation proceeds beyond the aldehyde stage to form carboxylic acids.
5. Conclude that the main products of oxidative cleavage of alkynes are carboxylic acids, which is consistent with the strong oxidative conditions that fully oxidize the carbon atoms involved in the triple bond.