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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2:56 minutes

Problem 13a

Textbook Question

Write the mechanism for each of the following reactions:
a. the reaction of acetyl chloride with water to form acetic acid

Verified step by step guidance

Identify the functional groups involved: Acetyl chloride (CH3COCl) is an acid chloride, and water (H2O) is a nucleophile. Acid chlorides are highly reactive due to the electron-withdrawing nature of the chlorine atom, making the carbonyl carbon highly electrophilic.

Step 1: Nucleophilic attack. The lone pair of electrons on the oxygen atom of water attacks the electrophilic carbonyl carbon of acetyl chloride. This forms a tetrahedral intermediate where the carbon is bonded to the original groups (CH3, Cl, and OH2+).

Step 2: Collapse of the tetrahedral intermediate. The negatively charged oxygen from the water attack donates its lone pair back to reform the carbonyl group, causing the chloride ion (Cl⁻) to leave as a leaving group. This step generates acetic acid (CH3COOH) and a chloride ion.

Step 3: Proton transfer. The intermediate acetic acid molecule may initially have an extra proton on the hydroxyl group (OH2+). A proton transfer occurs, either intramolecularly or with the help of another water molecule, to neutralize the charge and form the final acetic acid product.

Review the overall reaction: The reaction converts acetyl chloride (CH3COCl) and water (H2O) into acetic acid (CH3COOH) and hydrochloric acid (HCl). This is a nucleophilic acyl substitution reaction, where the chloride group is replaced by a hydroxyl group.

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Key Concepts

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

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of the acyl group. In the case of acetyl chloride reacting with water, water acts as the nucleophile, attacking the carbonyl carbon of acetyl chloride, resulting in the formation of acetic acid and hydrochloric acid.

Acyl Chlorides

Acyl chlorides, also known as acid chlorides, are reactive compounds derived from carboxylic acids by replacing the hydroxyl group with a chlorine atom. They are highly reactive due to the presence of the electronegative chlorine atom, which makes the carbonyl carbon more susceptible to nucleophilic attack. Understanding their reactivity is crucial for predicting the outcome of reactions involving acyl chlorides.

Hydrolysis Reactions

Hydrolysis reactions involve the reaction of a compound with water, leading to the breakdown of that compound. In organic chemistry, hydrolysis is often used to convert acyl chlorides into carboxylic acids. This reaction is typically exothermic and can be catalyzed by the presence of acids or bases, although in this case, water alone suffices to facilitate the conversion of acetyl chloride to acetic acid.

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Write the mechanism for each of the following reactions:a. the reaction of acetyl chloride with water to form acetic acid

Key Concepts

Nucleophilic Acyl Substitution

Acyl Chlorides

Hydrolysis Reactions

Watch next

Write the mechanism for each of the following reactions:
a. the reaction of acetyl chloride with water to form acetic acid