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

(a) hex-1-yne (b) hex-2-yne (c) hex-3-yne

(d) 2-methylhex-3-yne (e) cyclodecyne

Alkyne is oxidized using the oxidizing agent, e.g., potassium dichromate (KMnO₄), by supplying nascent oxygen.

Alkyne can oxidize in acidic and basic mediums using potassium dichromate(KMnO₄) reagent.

Alkyne, when reacted with cold aqueous potassium permanganate under neutral conditions, results in the formation of - diketone while the terminal alkyne forms keto-acid.

(a) Treating hex-1-yne with dilute, neutral KMnO₄forms 2-oxohexanoic acid.

(b) Treating hex-2-yne with dilute, neutral KMnO₄ forms 2-oxopentanoic acid.

(d) Treating 2-methylhex-3-yne with dilute, neutral KMnO₄ forms 2-methylhexane-3,4-dione.

(e) Treating cyclodecyne with dilute, neutral KMnO₄ forms cyclo-1,2-dione.

Alkyne when react with warm basic then dilute acid forms carboxylic acid while the terminal alkyne form carboxylic acid and carbon dioxide are released out.

(b)Treating hex-2-yne with warm basic KMnO₄ then dilute acid forms acetic acid and butyric acid.

(c) Treating hex-3-yne with warm basic KMnO₄ then dilute acid forms two equivalent propionic acids.

(d) Treating 2-methylhex-3-yne with warm basic KMnO₄ then dilute acid forms isobutyric acid and propionic acid.

Formation of isobutyric acid and propionic acid

(e) Treating cyclodecyne with warm basic KMnO₄ then dilute acid forms decanedioic acid.

Formation of decanedioic acid