The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert
a. fumaric acid to (±)-tartaric acid.
b. fumaric acid to meso-tartaric 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.

d. a mixture of osmic acid and hydrogen peroxide

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert

b. fumaric acid to meso-tartaric acid.

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(e)

Predict the major products of the following reactions.

f. 1-ethylcycloheptene + cold, dilute KMnO₄

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

c. 1-(hydroxymethyl)cyclohexanol

What stereoisomers are obtained from the reaction of each of the following alkenes with OsO₄ followed by aqueous H₂O₂?

a. trans-2-butene

b. cis-2-butene

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(f)

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(a)