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.
(a) hex-1-yne

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.

(d) 2-methylhex-3-yne

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

Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C₈H₁₂.

(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethyl sulfide, gives octanedioic acid, HOOC–(CH₂)₆–COOH. Draw the structure of W.

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.

(b) hex-2-yne

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.

(c) hex-3-yne

Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(a) oct-4-yne → butanoic acid

(b) trans-cyclodecene → decanedioic acid

When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

Predict the products of reaction of pent-1-yne with the following reagents.

g. cold, dilute KMnO₄

h. warm, concd. KMnO₄, NaOH

i. Na, liquid ammonia