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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3:01 minutes

Problem 6a

Textbook Question

Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.

Verified step by step guidance

Step 1: Identify the reactants and the product. Benzyl alcohol (C6H5CH2OH) reacts with acetyl chloride (CH3COCl) to form benzyl acetate (C6H5CH2OCOCH3). This is an esterification reaction where the hydroxyl group (-OH) of benzyl alcohol is replaced by an acetyl group (-COCH3).

Step 2: Recognize the role of acetyl chloride as an acylating agent. Acetyl chloride is highly reactive due to the presence of the carbonyl group (C=O) and the chlorine atom, which makes the carbonyl carbon electrophilic and susceptible to nucleophilic attack.

Step 3: Mechanism initiation: The lone pair of electrons on the oxygen atom of benzyl alcohol attacks the electrophilic carbonyl carbon of acetyl chloride. This forms a tetrahedral intermediate, and the chlorine atom is still attached to the carbonyl carbon.

Step 4: Collapse of the tetrahedral intermediate: The intermediate collapses, expelling the chloride ion (Cl⁻) as a leaving group. This results in the formation of the ester bond between the benzyl alcohol and the acetyl group.

Step 5: Final step: The chloride ion (Cl⁻) may react with a proton (H⁺) from the reaction medium to form HCl as a byproduct. The final product is benzyl acetate (C6H5CH2OCOCH3), an ester.

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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 an electrophilic carbonyl carbon, leading to the substitution of a leaving group. In this case, benzyl alcohol acts as the nucleophile, attacking the carbonyl carbon of acetyl chloride, which is a reactive acyl chloride. This mechanism is crucial for understanding how esters, like benzyl acetate, are formed from alcohols and acyl chlorides.

Role of Leaving Groups

In organic reactions, leaving groups are atoms or groups that can depart with a pair of electrons, facilitating the formation of new bonds. In the reaction between benzyl alcohol and acetyl chloride, the chloride ion (Cl-) is the leaving group. A good leaving group is essential for the reaction to proceed efficiently, as it stabilizes the transition state and allows the nucleophile to bond with the electrophile.

Formation of Esters

The formation of esters is a key reaction in organic chemistry, typically involving the reaction of an alcohol with a carboxylic acid or an acyl chloride. In this case, benzyl alcohol reacts with acetyl chloride to produce benzyl acetate. This reaction is significant in both synthetic organic chemistry and industrial applications, as esters are widely used in fragrances, flavorings, and as solvents.

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Textbook Question

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.

(a) ethyl propionate

(b) phenyl 3-methylhexanoate

Textbook Question

Which of the following proposed reactions would take place quickly under mild conditions?

(a)

(b)

(c)

(d)

(e)

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Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.

Textbook Question

Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.

Textbook Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(g)

Textbook Question

Show how you would use an acid chloride as an intermediate to synthesize.

(a) N-phenylbenzamide (PhCONHPh) from benzoic acid and aniline.

Textbook Question

Show how you would convert the following starting materials to the indicated nitriles:

(a) phenylacetic acid → phenylacetonitrile

Textbook Question

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

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