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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3:08 minutes

Problem 8e,f

Textbook Question

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(e) tert-butyl acetate
(f) diallyl succinate

Verified step by step guidance

Identify the esterification reaction: Esters are typically synthesized via a reaction between an acyl chloride and an alcohol in the presence of a base (e.g., pyridine) to neutralize the HCl byproduct.

For tert-butyl acetate: Recognize that the ester is composed of the tert-butyl group (from tert-butyl alcohol) and the acetate group (from acetic acid or its derivative). The acyl chloride needed is acetyl chloride (CH₃COCl), and the alcohol is tert-butyl alcohol ((CH₃)₃COH).

Write the reaction for tert-butyl acetate synthesis: Combine acetyl chloride (CH₃COCl) with tert-butyl alcohol ((CH₃)₃COH) in the presence of a base like pyridine. The reaction proceeds as follows:

CH₃COCl + (CH₃)₃COH → CH₃COO(C(CH₃)₃) + HCl

For diallyl succinate: Recognize that the ester is derived from succinic acid (or its derivative) and allyl alcohol. The acyl chloride needed is succinyl chloride (ClCO(CH₂)₂COCl), and the alcohol is allyl alcohol (CH₂=CHCH₂OH).

Write the reaction for diallyl succinate synthesis: Combine succinyl chloride (ClCO(CH₂)₂COCl) with two equivalents of allyl alcohol (CH₂=CHCH₂OH) in the presence of a base like pyridine. The reaction proceeds as follows:

ClCO(CH₂)₂COCl + 2CH₂=CHCH₂OH → (CH₂=CHCH₂OCO(CH₂)₂COOCH₂CH=CH₂) + 2HCl

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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, also known as acid chlorides, are reactive compounds derived from carboxylic acids by replacing the hydroxyl group (-OH) with a chlorine atom. They are highly reactive and serve as key intermediates in organic synthesis, particularly in the formation of esters and amides. Their reactivity allows them to easily react with alcohols to form esters through nucleophilic acyl substitution.

Esterification Reaction

Esterification is a chemical reaction that forms an ester from an alcohol and an acid (or acyl chloride). In this process, the hydroxyl group of the acid and a hydrogen atom from the alcohol are eliminated, resulting in the formation of an ester and water. This reaction is typically catalyzed by an acid and is crucial for synthesizing various esters, including those mentioned in the question.

Synthesis of Diallyl Succinate

Diallyl succinate is a diester formed from succinic acid and allyl alcohol. The synthesis involves the reaction of succinic acid's acyl chloride with two equivalents of allyl alcohol, leading to the formation of the diester. Understanding the structure of succinic acid and the reactivity of allyl alcohol is essential for successfully synthesizing this compound through esterification.

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Related Practice

Textbook Question

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

(b)

Textbook Question

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

(c)

Textbook Question

Propose a second mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the other oxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.

Textbook Question

Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an S_N2 reaction?

Textbook Question

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(a) N,N-dimethylacetamide

(b) acetanilide (PhNHCOCH₃)

Textbook Question

Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl acetate and (ii) N,N-diethylacetamide.

Textbook Question

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(e) cyclohexylamine → N-cyclohexylacetamide

(f) bromocyclohexane → dicyclohexylmethanol

Textbook Question

Predict the products of the following reactions.

(a)

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Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.(e) tert-butyl acetate(f) diallyl succinate

Key Concepts

Acyl Chlorides

Esterification Reaction

Synthesis of Diallyl Succinate

Watch next

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.
(e) tert-butyl acetate
(f) diallyl succinate