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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5:38 minutes

Problem 44a,b,c

Textbook Question

Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.
(a) ethanol
(b) sodium acetate
(c) aniline

Verified step by step guidance

Step 1: Recognize the functional group in benzoyl chloride (PhCOCl). It contains an acyl chloride group (-COCl), which is highly reactive and undergoes nucleophilic acyl substitution reactions.

Step 2: For reaction (a) with ethanol: Ethanol (CH3CH2OH) acts as a nucleophile. The lone pair on the oxygen atom of ethanol attacks the carbonyl carbon of benzoyl chloride, leading to the formation of an intermediate tetrahedral structure. The chloride ion (Cl⁻) is then eliminated, resulting in the formation of ethyl benzoate (PhCOOCH2CH3).

Step 3: For reaction (b) with sodium acetate: Sodium acetate (CH3COONa) contains the acetate ion (CH3COO⁻), which acts as a nucleophile. The acetate ion attacks the carbonyl carbon of benzoyl chloride, forming an intermediate. The chloride ion (Cl⁻) is displaced, leading to the formation of acetic anhydride (PhCOOCOCH3).

Step 4: For reaction (c) with aniline: Aniline (PhNH2) is a nucleophilic amine. The lone pair on the nitrogen atom of aniline attacks the carbonyl carbon of benzoyl chloride, forming an intermediate. The chloride ion (Cl⁻) is eliminated, resulting in the formation of N-phenylbenzamide (PhCONHPh).

Step 5: Summarize the reactions: (a) Ethanol forms ethyl benzoate, (b) Sodium acetate forms acetic anhydride, and (c) Aniline forms N-phenylbenzamide. These are all examples of nucleophilic acyl substitution reactions.

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Key Concepts

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

Acyl Chlorides

Acyl chlorides, such as benzoyl chloride, are reactive compounds that contain a carbonyl group (C=O) bonded to a chlorine atom. They are known for their ability to undergo nucleophilic acyl substitution reactions, where the chlorine atom is replaced by a nucleophile. Understanding the reactivity of acyl chlorides is crucial for predicting the products of their reactions with various nucleophiles.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, leading to the replacement of a leaving group. In the case of benzoyl chloride, the nucleophile can be an alcohol, an amine, or a carboxylate ion, each resulting in different products. Recognizing the nature of the nucleophile is essential for predicting the outcome of the reaction.

Product Formation

The formation of products in organic reactions depends on the nature of the reactants and the reaction conditions. For benzoyl chloride, the products formed when reacting with ethanol, sodium acetate, and aniline will vary based on the nucleophilic character of each reagent. Understanding how to identify and predict these products is key to mastering organic synthesis and reaction mechanisms.

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