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

19. Reactions of Aromatics: EAS and Beyond

Diazo Retrosynthesis

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Diazo Retrosynthesis

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2:30 minutes

Problem 35

Textbook Question

Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?

Verified step by step guidance

Identify the structure of temozolomide and locate the amide bonds present in the molecule. Amide bonds are characterized by the functional group \( \text{C=O} \) (carbonyl) directly bonded to a nitrogen atom (\( \text{N} \)).

Understand the mechanism of hydrolysis. In the first step of the conversion, hydrolysis typically involves the cleavage of an amide bond by the addition of water (\( \text{H}_2\text{O} \)), breaking it into a carboxylic acid derivative and an amine or ammonia.

Analyze the reaction pathway of temozolomide to methyldiazonium. The hydrolysis step specifically targets the amide bond that leads to the formation of the intermediate compound necessary for the generation of methyldiazonium.

Determine which amide bond in temozolomide is positioned to undergo hydrolysis based on the electronic and steric environment. The bond most susceptible to hydrolysis is typically the one that facilitates the formation of a stable intermediate or product.

Conclude that the amide bond hydrolyzed in the first step is the one that directly contributes to the release of the methyldiazonium ion precursor, as this is the key transformation in the reaction pathway.

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Key Concepts

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

Amide Bond

An amide bond is a functional group characterized by a carbonyl group (C=O) directly attached to a nitrogen atom (N). It is formed through a reaction between a carboxylic acid and an amine, resulting in the release of water. Understanding the structure and reactivity of amide bonds is crucial for predicting their behavior in chemical reactions, such as hydrolysis.

Hydrolysis

Hydrolysis is a chemical reaction involving the breakdown of a compound by water. In the context of amides, hydrolysis typically results in the formation of a carboxylic acid and an amine. This reaction can be catalyzed by acids or bases and is essential for understanding the conversion processes in organic chemistry, including the transformation of temozolomide.

Temozolomide Conversion

Temozolomide is an alkylating agent used in cancer treatment, which undergoes conversion to methyldiazonium through a series of chemical reactions. The initial step involves the hydrolysis of an amide bond, leading to the formation of reactive intermediates. Understanding this conversion is vital for grasping the drug's mechanism of action and its therapeutic implications.

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Textbook Question

Draw the structure of the activated benzene ring and the diazonium ion used in the synthesis of each of the following compounds, whose structures can be found on page 607.

b. methyl orange

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Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.

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Show how you would convert aniline to the following compounds.

Textbook Question

Show how you would convert aniline to the following compounds.

(g) phenol

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Conversion of t-butylbenzene to a phenol results in two products when the reaction occurs through the benzyne mechanism. Devise a sequence involving a diazonium ion in which only one phenol product is produced.

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Synthesize the dye shown starting with aniline and naphthol using reactions from Chapters 23 and 24. [Hint. Start by identifying how each substituent might be installed and then plan the order of their introduction.]

Textbook Question

Draw the structure of the activated benzene ring and the diazonium ion used in the synthesis of each of the following compounds, whose structures can be found on page 607.

b. methyl orange

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