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

Carboxylic Acid Derivatives

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid Derivatives

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4:34 minutes

Problem 57d

Textbook Question

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.
(d)

Verified step by step guidance

Step 1: Protect the phenolic hydroxyl groups of gallic acid by methylation. Use a methylating agent such as dimethyl sulfate or methyl iodide in the presence of a base like potassium carbonate to convert the hydroxyl groups into methoxy groups. This will yield trimethoxybenzoic acid.

Step 2: Reduce the carboxylic acid group of trimethoxybenzoic acid to an aldehyde. This can be accomplished using a reagent like diisobutylaluminum hydride (DIBAL-H) under controlled conditions to selectively reduce the carboxylic acid to an aldehyde, forming trimethoxybenzaldehyde.

Step 3: Perform a reductive amination reaction to introduce the ethylamine group. React trimethoxybenzaldehyde with ethylamine in the presence of a reducing agent such as sodium cyanoborohydride (NaBH3CN) or hydrogen gas with a catalyst like palladium on carbon (Pd/C). This will yield mescaline.

Step 4: Purify the product using techniques such as recrystallization or chromatography to isolate mescaline from any side products or unreacted starting materials.

Step 5: Confirm the structure of mescaline using spectroscopic methods such as NMR (nuclear magnetic resonance) and IR (infrared spectroscopy) to ensure the synthesis was successful.

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Key Concepts

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

Multistep Synthesis

Multistep synthesis involves a series of chemical reactions that transform a starting material into a desired product through intermediate compounds. Each step typically requires specific reagents and conditions, and understanding the reactivity of functional groups is crucial for planning the sequence of reactions effectively.

Reagents and Reaction Conditions

Reagents are substances used to bring about a chemical reaction, while reaction conditions include temperature, pressure, and solvent choice. Selecting the appropriate reagents and optimizing conditions are essential for achieving high yields and desired selectivity in each step of the synthesis.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another during a chemical reaction. This concept is vital in organic synthesis, as it allows chemists to modify the structure and properties of molecules, facilitating the construction of complex organic compounds from simpler precursors.

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Related Practice

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(a)

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(b)

Textbook Question

Show how you would accomplish the following syntheses in good yields.

(h)

Textbook Question

Show how you would accomplish the following multistep syntheses, using the indicated starting material and any necessary reagents.

(c)

Textbook Question

Peroxyacetic acid (bp = 105 °C) has a lower boiling point than acetic acid (bp = 118 °C), even though peroxyacetic acid has a higher molecular weight. Explain why peroxyacetic acid is more volatile than acetic acid.

Multiple Choice

Which of the following is NOT a carboxylic acid derivative?

Textbook Question

For each heterocyclic compound,

(i) explain what type of acid derivative is present.

(a)

(b)

(c)

Textbook Question

The structures of four useful polymers are shown, together with some of their best-known products. In each case,

(i) determine the kind of polymer (polyamide, polyester, etc.).

(c)