Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

10. Addition Reactions

Acid-Catalyzed Hydration

Organic Chemistry

10. Addition Reactions

Acid-Catalyzed Hydration

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1:52 minutes

Problem 99

Textbook Question

When fumarate reacts with D₂O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti addition of D₂O?

Verified step by step guidance

Step 1: Analyze the structure of fumarate, which is a trans-alkene with two carboxylate groups (-COO⁻) and two hydrogens attached to the double bond. The trans configuration means the substituents on the double bond are on opposite sides.

Step 2: Observe the product structure. The addition of D2O results in the formation of a single isomer where the deuterium (D) and hydroxyl (OH) groups are added to the carbons of the former double bond. Both D and OH are added to the same face of the molecule.

Step 3: Recall the difference between syn and anti addition. Syn addition occurs when both groups are added to the same face of the double bond, while anti addition occurs when the groups are added to opposite faces.

Step 4: Based on the product structure, where both D and OH are added to the same face, the reaction catalyzed by fumarase is a syn addition of D2O.

Step 5: Conclude that the enzyme fumarase specifically catalyzes a stereospecific syn addition of D2O to fumarate, resulting in the observed single isomer product.

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Key Concepts

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

Fumarate and Fumarase

Fumarate is a dicarboxylic acid and an important intermediate in the citric acid cycle. Fumarase is an enzyme that catalyzes the reversible hydration of fumarate to malate. Understanding the structure of fumarate and the role of fumarase is crucial for analyzing how the enzyme facilitates the addition of water (D2O) to fumarate.

Addition Reactions

Addition reactions involve the addition of atoms or groups to a molecule, typically across a double bond. In the context of fumarate reacting with D2O, it is important to determine whether the addition occurs in a syn (same side) or anti (opposite sides) manner, as this affects the stereochemistry of the product formed.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the case of fumarate and D2O, understanding whether the enzyme catalyzes a syn or anti addition is essential for predicting the stereochemical outcome of the reaction and the specific isomer produced.

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Related Practice

Textbook Question

Propose a mechanism to show how 3,3-dimethylbut-1-ene reacts with dilute aqueous H₂SO₄ to give 2,3-dimethylbutan-2-ol and a small amount of 2,3-dimethylbut-2-ene.

HINT: When predicting products for electrophilic additions, first draw the structure of the carbocation (or other intermediate) that results from electrophilic attack.