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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2:02 minutes

Problem 50a

Textbook Question

Predict the products of the following reactions.
(a)

Verified step by step guidance

Step 1: Identify the functional groups in the reactants. The first reactant is benzoyl chloride (C6H5COCl), which contains an acyl chloride group. The second reactant is cyclohexanol, which contains a hydroxyl (-OH) group.

Step 2: Recognize the type of reaction. This is a nucleophilic acyl substitution reaction, where the hydroxyl group of cyclohexanol acts as a nucleophile and attacks the carbonyl carbon of benzoyl chloride.

Step 3: Describe the mechanism. The nucleophilic attack occurs as the lone pair of electrons on the oxygen atom of the hydroxyl group attacks the electrophilic carbonyl carbon of benzoyl chloride. This leads to the formation of a tetrahedral intermediate.

Step 4: Explain the elimination step. The tetrahedral intermediate collapses, expelling the chloride ion (Cl⁻) as a leaving group and forming an ester bond between the benzoyl group and cyclohexanol.

Step 5: Predict the product. The final product is cyclohexyl benzoate (C6H5COO-cyclohexyl), an ester formed by the reaction of benzoyl chloride and cyclohexanol.

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Key Concepts

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

Carboxylic Acid Derivatives

Carboxylic acid derivatives, such as acyl chlorides, esters, and anhydrides, are compounds that can be derived from carboxylic acids. They retain the carbonyl (C=O) group and can undergo nucleophilic acyl substitution reactions. In this reaction, the acyl chloride reacts with an alcohol, where the alcohol acts as a nucleophile, attacking the carbonyl carbon and leading to the formation of an ester.

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the electrophilic carbon of a carbonyl group in a carboxylic acid derivative. This process typically involves the formation of a tetrahedral intermediate, followed by the elimination of a leaving group, such as chloride in the case of acyl chlorides. This reaction is crucial for synthesizing esters and other derivatives.

Reaction Mechanism

Understanding the reaction mechanism is essential for predicting the products of organic reactions. It involves a step-by-step description of how reactants transform into products, including the movement of electrons and the formation and breaking of bonds. In this case, the mechanism will illustrate how the nucleophile (alcohol) attacks the electrophilic carbon of the acyl chloride, leading to the formation of an ester and the release of hydrochloric acid.

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Predict the products of the following reactions.(a)

Key Concepts

Carboxylic Acid Derivatives

Nucleophilic Acyl Substitution

Reaction Mechanism

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Predict the products of the following reactions.
(a)