Directions: This section contains 1 paragraph. Based upon the paragraph, 3 multiple choice questions have to be answered. Each question has 4 choices (a), (b), (c) and (d), out of which ONLY ONE is correct. Passage I Alkenes undergo a variety of reactions like hydrogenation, halogenation, oxidation, epoxidation and so on. The double bond of the alkenes acts as electron donor. An unsaturated hydrocarbon gave, on treatment with alkaline \(\mathrm{KMnO}_{4}\) under hot conditions, one mole of adipic acid. The unsaturated hydrocarbon could be (a) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) (b) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}_{2}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)

Step by step solution

01

Analyze the provided unsaturated hydrocarbons

From the options provided, let's assign each hydrocarbon a letter to work with them easily: (a) X = \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) (b) Y = \(\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}_{2}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)

02

Write down the molecular formula of adipic acid

Adipic acid has the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{4}\).

03

Perform KMnO4 oxidation on each hydrocarbon

Oxidation through alkaline KMnO4 at hot conditions breaks both double and triple bonds in alkenes and alkynes, respectively, and adds an equal number of hydroxyl groups to the carbons involved. Now, let's perform this oxidation on each hydrocarbon: (a) X: \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C}(\mathrm{OH})_{2}-\mathrm{C}(\mathrm{OH})_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) (b) Y: \(\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}_{2}-\mathrm{C}(\mathrm{OH})_{2}-\mathrm{C}(\mathrm{OH})_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)

04

Compare the oxidation products with adipic acid

As we compare the products of each hydrocarbon after oxidation with adipic acid, we find that only the (b) hydrocarbon, Y, yields adipic acid after oxidation. Therefore, the unsaturated hydrocarbon that yields adipic acid when treated with alkaline KMnO4 under hot conditions is: Answer: (b) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{CH}_{2}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\)

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