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Ch.8 - Reactions of Alkenes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.8 - Reactions of AlkenesProblem 65a,b
Chapter 8, Problem 65a,b

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.
Structural formulas of fumaric acid, maleic acid, and tartaric acid, illustrating their chemical structures and relationships.
Show how you would convert
a. fumaric acid to (±)-tartaric acid.
b. fumaric acid to meso-tartaric acid.

Verified step by step guidance
1
Step 1: Recognize the structural difference between fumaric acid (trans-butenedioic acid) and tartaric acid. Fumaric acid has a double bond between the two central carbons, while tartaric acid has hydroxyl (-OH) groups attached to these carbons, making it a dihydroxy derivative.
Step 2: To convert fumaric acid to (+/-)-tartaric acid, perform a hydroxylation reaction. Use a reagent such as potassium permanganate (KMnO₄) or osmium tetroxide (OsO₄) in the presence of water. These reagents add hydroxyl groups across the double bond in a syn addition manner, resulting in a racemic mixture of tartaric acid.
Step 3: To convert fumaric acid to meso-tartaric acid, use a similar hydroxylation reaction but ensure the reaction conditions favor the formation of the meso compound. The meso form arises due to the symmetrical addition of hydroxyl groups across the double bond, leading to a molecule with internal symmetry.
Step 4: Understand the stereochemistry involved. The racemic tartaric acid contains both enantiomers (R,R and S,S configurations), while meso-tartaric acid is achiral due to its plane of symmetry.
Step 5: Verify the product by analyzing the stereochemistry and symmetry of the resulting tartaric acid. The meso-tartaric acid will have identical groups on both sides of the molecule, while the racemic tartaric acid will consist of two non-superimposable mirror images.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Geometric Isomerism

Geometric isomerism occurs due to the restricted rotation around double bonds, leading to different spatial arrangements of atoms. In the case of fumaric acid (trans) and maleic acid (cis), the positioning of the carboxylic acid groups relative to the double bond defines their distinct properties and reactivity. Understanding this concept is crucial for predicting the outcomes of reactions involving these isomers.
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Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. Tartaric acid, which can exist in multiple stereoisomeric forms, including meso and enantiomers, exemplifies the importance of stereochemistry in organic reactions. Recognizing the stereochemical configurations is essential for converting fumaric acid to the desired tartaric acid forms.
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Reactions of Alkenes

The conversion of fumaric acid to tartaric acid involves reactions typical of alkenes, such as hydration or oxidation. These reactions can introduce functional groups or change the configuration of the molecule. Familiarity with the mechanisms of these reactions, including the addition of water across the double bond, is vital for successfully synthesizing tartaric acid from fumaric acid.
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Related Practice
Textbook Question

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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Textbook Question

In contact with a platinum catalyst, an unknown alkene reacts with three equivalents of hydrogen gas to give 1-isopropyl-4-methylcyclohexane. When the unknown alkene is ozonized and reduced, the products are the following:

Deduce the structure of the unknown alkene.

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Textbook Question

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

c. maleic acid to (±)-tartaric acid.

2
views
Textbook Question

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.

1
views
Textbook Question

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.

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Textbook Question

Propose a mechanism for the following reaction.

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