10. Addition Reactions

Predict the product of the following reaction.

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. <IMAGE>

e. hot, concentrated potassium permanganate

Predict the major products of the following reactions.

e. 1-ethylcycloheptene + warm, concentrated KMnO4

Problem-Solving Hint: Three reagents oxidize the pi bond of an alkene but leave the sigma bond intact: (a) cold, dilute KMnO4; (b) OsO4-H2O2; and (c) RCO3H epoxidation.

Two reagents break the double bond entirely, giving carbonyl groups: (a) warm, concentrated KMnO4 and (b) O3 followed by (CH3)2S.

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.

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