10. Addition Reactions

Which of the following correctly represents the products formed when 1-butene undergoes oxidative cleavage with hot, concentrated ${\mathrm{KMnO}}_4$ under acidic conditions?

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

Predict the product of the following reaction.

What alkene would give only a ketone with three carbons as a product of oxidative cleavage?

Predict the major products of the following reactions.

(b) (Z)-3-methyloct-3-ene + warm, concentrated KMnO₄

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(k)

The sex attractant of the housefly has the formula C₂₃H₄₆. When treated with warm potassium permanganate, this pheromone gives two products: CH₃(CH₂)₁₂COOH and CH₃(CH₂)₇COOH. Suggest a structure for this sex attractant. Explain which part of the structure is uncertain.

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(b) hex-3-ene → propanoic acid

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

(e) hot, concentrated potassium permanganate

Predict the major products of the following reactions.

(e) 1-ethylcycloheptene + warm, concentrated KMnO₄

Unknown X, C₅H₉Br does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C₅H₈. Unlike X, Y decolorizes bromine and changes KMnO₄ from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C₅H₈O₂. Propose consistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

An unknown compound decolorizes bromine in carbon tetrachloride, and it undergoes catalytic reduction to give decalin. When treated with warm, concentrated potassium permanganate, this compound gives cis-cyclohexane-1,2-dicarboxylic acid and oxalic acid. Propose a structure for the unknown compound.