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

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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3:50 minutes

Problem 59a

Textbook Question

What products would you expect to obtain from the following reactions?
a. malonic acid + 2 acetyl chloride

Verified step by step guidance

Step 1: Recognize the functional groups in the reactants. Malonic acid contains two carboxylic acid groups (-COOH), and acetyl chloride is an acid chloride (-COCl). Acid chlorides are highly reactive and can undergo acylation reactions with nucleophiles like the hydroxyl groups in malonic acid.

Step 2: Understand the reaction mechanism. The hydroxyl group (-OH) of malonic acid will act as a nucleophile and attack the carbonyl carbon of acetyl chloride. This results in the formation of an ester bond and the release of HCl as a byproduct.

Step 3: Consider the stoichiometry of the reaction. Since there are two hydroxyl groups in malonic acid and two molecules of acetyl chloride, each hydroxyl group can react with one acetyl chloride molecule, leading to the formation of a diester.

Step 4: Write the structure of the product. The product will be a diester where both carboxylic acid groups of malonic acid are converted into ester groups by reacting with acetyl chloride. The general structure will be CH2(COOR)2, where R is the acetyl group (CH3CO).

Step 5: Account for byproducts. Each reaction between a hydroxyl group and acetyl chloride releases HCl as a byproduct. Since two acetyl chloride molecules are used, two molecules of HCl will be produced in this reaction.

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Key Concepts

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

Malonic Acid

Malonic acid is a dicarboxylic acid with the formula C3H4O4. It contains two carboxyl groups (-COOH) and is commonly used in organic synthesis. Its structure allows it to undergo various reactions, including esterification and acylation, making it a versatile building block in the synthesis of more complex molecules.

Acyl Chlorides

Acyl chlorides, also known as acid chlorides, are derivatives of carboxylic acids where the hydroxyl group is replaced by a chlorine atom. They are highly reactive and are often used in acylation reactions to introduce acyl groups into organic compounds. In the presence of nucleophiles, acyl chlorides readily react to form esters, amides, or other acyl derivatives.

Reactions of Malonic Acid with Acyl Chlorides

When malonic acid reacts with acyl chlorides, it typically undergoes a reaction known as acylation, leading to the formation of malonic acid derivatives. In this case, two acetyl chlorides would introduce two acetyl groups into the malonic acid structure, resulting in the formation of a diacetyl derivative. This reaction is significant in synthetic organic chemistry for constructing complex molecules.

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