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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5:47 minutes

Problem 12e

Textbook Question

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
e.

Verified step by step guidance

Step 1: Identify the functional group in the target compound. The compound contains an ester functional group, specifically ethyl pentyl ester.

Step 2: Recognize that acetyl chloride (CH3COCl) is an acyl chloride, which is reactive and can be converted into an ester through nucleophilic acyl substitution.

Step 3: Determine the neutral nucleophile required to form the ester. To synthesize the target compound, the nucleophile must be cyclopentanol (C5H9OH), as it provides the cyclopentyl group in the ester.

Step 4: Outline the reaction mechanism. Acetyl chloride reacts with cyclopentanol in the presence of a base (such as pyridine) to neutralize the HCl byproduct. The nucleophilic oxygen of cyclopentanol attacks the carbonyl carbon of acetyl chloride, forming the ester bond.

Step 5: Ensure proper reaction conditions. The reaction should be carried out under anhydrous conditions to prevent hydrolysis of acetyl chloride, and a base like pyridine is used to absorb the HCl formed during the reaction.

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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 in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, such as an acid chloride, leading to the replacement of a leaving group (like chloride) with the nucleophile. This reaction is crucial for synthesizing various organic compounds, including esters and amides.

Acetyl Chloride

Acetyl chloride is an acyl chloride derived from acetic acid, characterized by the presence of a carbonyl group (C=O) and a chlorine atom. It is a reactive electrophile commonly used in organic synthesis to introduce acetyl groups into nucleophiles, facilitating the formation of esters and other derivatives through nucleophilic acyl substitution.

Neutral Nucleophiles

Neutral nucleophiles are species that possess a lone pair of electrons and can donate them to electrophiles without carrying a formal charge. Examples include alcohols, amines, and water. In the context of nucleophilic acyl substitution, a neutral nucleophile can effectively attack the carbonyl carbon of acetyl chloride, leading to the formation of a new compound.

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Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds? e.

Key Concepts

Nucleophilic Acyl Substitution

Acetyl Chloride

Neutral Nucleophiles

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Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?
e.