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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 65b
Chapter 8, Problem 65b

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
b. fumaric acid to meso-tartaric acid.

Verified step by step guidance
1
Step 1: Recognize that fumaric acid is the trans isomer of butenedioic acid, and meso-tartaric acid is a dihydroxy derivative with two hydroxyl groups added to the carbon-carbon double bond.
Step 2: Understand that the conversion involves the addition of hydroxyl groups (OH) to the double bond in fumaric acid. This reaction is typically achieved through a hydroxylation process using a reagent such as potassium permanganate (KMnO₄) or osmium tetroxide (OsO₄).
Step 3: During hydroxylation, the addition of hydroxyl groups occurs in a syn fashion, meaning both hydroxyl groups are added to the same side of the molecule. This is crucial for forming the meso compound, which has internal symmetry.
Step 4: Analyze the stereochemistry of the product. Since fumaric acid is trans, the hydroxyl groups added to the double bond will result in a meso-tartaric acid structure, where the molecule has a plane of symmetry and is optically inactive.
Step 5: Verify the structure of meso-tartaric acid, which has the formula HOOC-CH(OH)-CH(OH)-COOH. Ensure that the hydroxyl groups are positioned on adjacent carbons and the molecule exhibits internal symmetry.

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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 in compounds with restricted rotation around a double bond, 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 recognizing how structural differences influence chemical behavior.
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Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical properties and reactions. Meso-tartaric acid, which has two stereocenters but is achiral due to its internal plane of symmetry, exemplifies the importance of stereochemistry in determining the optical activity of compounds. This concept is essential for understanding how to convert fumaric acid into meso-tartaric acid.
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Hydroxylation Reaction

Hydroxylation is a chemical reaction that introduces hydroxyl (-OH) groups into a molecule, often through the addition of water across a double bond. In the conversion of fumaric acid to meso-tartaric acid, hydroxylation occurs at the double bond, resulting in the formation of two new hydroxyl groups. This reaction is a key step in synthesizing tartaric acid from fumaric acid.
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Related Practice
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

a. fumaric acid to (±)-tartaric acid.

b. fumaric acid to meso-tartaric acid.

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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 following cyclization has been observed in the oxymercuration-demercuration of this unsaturated alcohol. Propose a mechanism for this reaction.

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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.

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Textbook Question

Propose a mechanism for the following reaction.

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