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

EAS:Retrosynthesis

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

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4:46 minutes

Problem 44

Textbook Question

Provide the necessary reagents next to the arrows.

Verified step by step guidance

Analyze the reaction scheme provided. Identify the starting material, the intermediate(s), and the final product. This will help you determine the type of reaction(s) involved (e.g., substitution, elimination, addition, oxidation, reduction, etc.).

Determine the functional group transformations occurring in each step. For example, if an alcohol is converted to a ketone, this suggests an oxidation reaction.

Based on the functional group transformation, select the appropriate reagent(s). For example, if an alkene is being converted to an alcohol, reagents like BH₃/THF followed by H₂O₂/NaOH (hydroboration-oxidation) or Hg(OAc)₂/H₂O followed by NaBH₄ (oxymercuration-demercuration) might be used.

Consider the reaction conditions (e.g., temperature, solvent, and stereochemistry). For example, if stereospecificity is required, choose reagents that provide the desired stereochemical outcome.

Write the reagents next to the arrows in the reaction scheme, ensuring they correspond to the transformations occurring in each step. Double-check that the reagents are appropriate for the specific reaction type and conditions.

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Key Concepts

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

Reagents in Organic Reactions

Reagents are substances that are added to a chemical reaction to cause a transformation. In organic chemistry, they can include acids, bases, oxidizing agents, reducing agents, and catalysts. Understanding the role of each reagent is crucial for predicting the outcome of a reaction and determining the necessary conditions for the reaction to proceed.

Reaction Mechanisms

A reaction mechanism describes the step-by-step process by which reactants are converted into products. It includes the breaking and forming of bonds, the movement of electrons, and the intermediates formed during the reaction. Familiarity with mechanisms helps in understanding how reagents interact and the specific conditions required for a reaction to occur.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. They determine the reactivity and properties of organic compounds. Recognizing functional groups is essential for predicting how different reagents will interact with a substrate in a reaction.

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Benzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acyl chloride was used in the Friedel–Crafts acylation?

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Beginning with benzene, synthesize the benzyl bromide shown.

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Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.

(d)

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Phenolphthalein, a common nonprescription laxative, is also an acid–base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

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Textbook Question

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