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

20. Phenols

Phenol Acidity

Organic Chemistry

20. Phenols

Phenol Acidity

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13:38 minutes

Problem 60

Textbook Question

Sulpiride is an antipsychotic. Provide the reagents (a) and (b) used to complete the synthesis.

Verified step by step guidance

Step 1: Analyze the first transformation. The starting material is a sulfonamide with a hydroxyl group. The product has an additional carbonyl group adjacent to the hydroxyl group, suggesting an acylation reaction. Consider using an acyl chloride or anhydride as reagent (a) to introduce the acyl group.

Step 2: Consider the mechanism for the acylation. The hydroxyl group can act as a nucleophile, attacking the electrophilic carbonyl carbon of the acyl chloride or anhydride, leading to the formation of an ester linkage.

Step 3: Analyze the second transformation. The intermediate product has a carbonyl group and the final product has an additional nitrogen-containing ring structure. This suggests a nucleophilic substitution reaction where the nitrogen atom of the ring structure attacks the carbonyl carbon.

Step 4: Consider the mechanism for the nucleophilic substitution. The nitrogen atom in the ring structure can act as a nucleophile, attacking the electrophilic carbonyl carbon, leading to the formation of an amide linkage.

Step 5: Identify reagent (b) as a nitrogen-containing compound, such as a cyclic amine, that can undergo nucleophilic attack on the carbonyl group to form the final product, Sulpiride.

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Key Concepts

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

Sulfonamide Chemistry

Sulfonamides are a class of organic compounds characterized by the presence of a sulfonyl group attached to an amine. They are crucial in pharmaceuticals due to their antibacterial properties. Understanding the reactivity and synthesis of sulfonamides is essential for designing drugs like Sulpiride, which involves the transformation of sulfonamide precursors.

Amide Bond Formation

Amide bond formation is a fundamental reaction in organic chemistry, often used in the synthesis of pharmaceuticals. It involves the reaction between a carboxylic acid derivative and an amine, forming an amide linkage. This process is key in the synthesis of Sulpiride, where amide bonds are formed to build the drug's complex structure.

Reagent Selection in Organic Synthesis

Choosing appropriate reagents is critical in organic synthesis to achieve desired transformations efficiently. Reagents are selected based on their ability to facilitate specific chemical reactions, such as oxidation, reduction, or functional group interconversion. In the synthesis of Sulpiride, selecting reagents (a) and (b) is crucial for progressing through the synthetic pathway to achieve the final product.

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Predict the products formed when m-cresol (m-methylphenol) reacts with

(a) NaOH and then ethyl bromide

Textbook Question

Predict the major products of the following reactions.

(b) phenol + tert-butyl chloride + AlCl₃

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The dye alizarin normally forms an orange solution when dissolved. However, if KOEt is added to the solution, it turns blue very rapidly. Rationalize this result.

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Rationalize the fact that 1,4-dihydroxybenzene melts at a significantly higher temperature than 1,2-diydroxybenzene.

Textbook Question

Phenol is synthesized from cumene via the scheme shown. Suggest the mechanism for each step of the reaction shown. [The oxygens have been screened in blue and orange to assist you.]

Textbook Question

Though the nitro group is electron-withdrawing by resonance, when in the meta position, it doesn’t communicate by resonance with the phenoxide anion. And yet, the pKₐ value of m-nitrophenol is lowered from 10 (the pKₐ value of unsubstituted phenol) to 8.4. Explain this observation.

Textbook Question

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

(c)

Textbook Question

The following reaction proceeds in good yield, despite requiring high temperature and high concentration. Identify the product you’d expect to obtain in this reaction.

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