Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO₄ and (2) warm basic KMnO₄, then dilute acid.
(e) cyclodecyne

Verified step by step guidance

1. Identify the functional group in cyclodecyne. Cyclodecyne is an alkyne, which contains a triple bond between two carbon atoms in a 10-membered ring structure.
2. Understand the reaction with dilute, neutral KMnO4. This reagent typically adds hydroxyl groups (-OH) across the triple bond, resulting in a dihydroxylated intermediate (a vicinal diol).
3. Understand the reaction with warm, basic KMnO4 followed by dilute acid. Under these conditions, the triple bond undergoes oxidative cleavage, breaking the bond completely and forming carboxylic acids at the ends of the cleaved bond.
4. Apply the oxidative cleavage to cyclodecyne. Since the triple bond is part of a ring, breaking it will open the ring, resulting in a linear structure with carboxylic acid groups at both ends.
5. Summarize the products: (1) Reaction with dilute, neutral KMnO4 produces a vicinal diol. (2) Reaction with warm, basic KMnO4 followed by dilute acid produces a dicarboxylic acid (a linear molecule with carboxylic acid groups at both ends).

Key Concepts

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In organic chemistry, these reactions often lead to the formation of alcohols, ketones, or carboxylic acids. Understanding how different reagents, like KMnO4, act as oxidizing agents is crucial for predicting the products of reactions involving unsaturated hydrocarbons.

KMnO4 as an Oxidizing Agent

Potassium permanganate (KMnO4) is a strong oxidizing agent used in organic synthesis. In dilute, neutral conditions, it typically oxidizes alkenes and alkynes to form diols, while in warm basic conditions, it can cleave double or triple bonds, leading to the formation of carboxylic acids or ketones. The specific conditions dictate the extent and type of oxidation that occurs.

Cyclodecyne Structure and Reactivity

Cyclodecyne is a cyclic alkyne with a triple bond in its structure, which makes it more reactive than alkenes or alkanes. The presence of the triple bond allows for various reactions, including oxidation. Understanding the structure and reactivity of cyclodecyne is essential for predicting the products formed when it undergoes treatment with KMnO4 under different conditions.