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

26. Amines

Amine Alkylation

Organic Chemistry

26. Amines

Amine Alkylation

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3:24 minutes

Problem 53a

Textbook Question

Two widely used pain relievers are aspirin and acetaminophen. Show how you would synthesize these drugs from phenol.

Verified step by step guidance

Step 1: Begin with phenol (C₆H₅OH) as the starting material. Phenol has a hydroxyl (-OH) group attached to a benzene ring, which can be functionalized to create both aspirin and acetaminophen.

Step 2: To synthesize acetaminophen, first convert phenol into para-aminophenol. This can be achieved by nitration of phenol to form para-nitrophenol, followed by reduction of the nitro group (-NO₂) to an amine group (-NH₂).

Step 3: Acetylate the para-aminophenol by reacting it with acetic anhydride (CH₃CO)₂O. This introduces the acetyl group (-COCH₃) to the amine group, forming acetaminophen (C₆H₄OHNHCOCH₃).

Step 4: To synthesize aspirin, first convert phenol into salicylic acid. This can be done by Kolbe-Schmitt reaction, where phenol reacts with carbon dioxide (CO₂) under basic conditions to form salicylic acid (C₆H₄OHCOOH).

Step 5: Acetylate salicylic acid by reacting it with acetic anhydride (CH₃CO)₂O. This introduces the acetyl group (-COCH₃) to the hydroxyl group, forming aspirin (C₆H₄COOHCOCH₃).

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Key Concepts

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

Phenol

Phenol is an aromatic compound characterized by a hydroxyl group (-OH) attached to a benzene ring. It serves as a key starting material in organic synthesis, particularly for the production of various pharmaceuticals, including aspirin and acetaminophen. Understanding its reactivity and functional group transformations is essential for synthesizing these drugs.

Acetaminophen Synthesis

Acetaminophen, or paracetamol, can be synthesized from phenol through a two-step process: first, phenol is converted to an aniline derivative via nitration and reduction, followed by acetylation of the amine group. This process highlights the importance of functional group transformations in organic synthesis, particularly in drug development.

Aspirin Synthesis

Aspirin, or acetylsalicylic acid, can be synthesized from phenol by first converting it to salicylic acid through a hydroxylation reaction, followed by acetylation of the hydroxyl group. This synthesis pathway illustrates the significance of esterification reactions in organic chemistry, particularly in the context of creating analgesic compounds.

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Textbook Question

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(c) The pK_b of this compound is −2.3, making it not only a stronger base than a typical aniline, but even stronger than hydroxide ion. Explain its remarkable basicity.

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Textbook Question

Rank the amines in each set in order of increasing basicity.

(d)

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Textbook Question

Within each structure, rank the indicated nitrogens by increasing basicity.

(f)

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Textbook Question

Predict the products of the following reactions.

(d)

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Textbook Question

Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA.

b. Explain why it can cross-link DNA.

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Textbook Question

In Section 10.12, we saw that S-adenosylmethionine (SAM) methylates the nitrogen atom of noradrenaline to form adrenaline, a more potent hormone. If SAM methylates an OH group attached to the benzene ring instead, it completely destroys noradrenaline's activity.

b. Which reaction is more apt to occur, methylation on nitrogen or methylation on oxygen?

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Textbook Question

Dimethylamine, (CH₃)₂NH, has a molecular weight of 45 and a boiling point of 7.4 °C. Trimethylamine, (CH₃)₃N, has a higher molecular weight (59) but a lower boiling point (3.5 °C). Explain this apparent discrepancy.

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Textbook Question

Rank the following substituted anilines from most basic to least basic:

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