1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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

25. Condensation Chemistry

Condensation Reactions

Organic Chemistry

25. Condensation Chemistry

Condensation Reactions

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3:23 minutes

Problem 17Bruice - 8th Edition

Textbook Question

Draw the products of the following reactions: d.

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Identify the functional groups in the reactant: a chloro group, an ester group, and a nitro group.

Recognize that the hydroxide ion (OH-) is a strong nucleophile and base.

Determine the most likely site for nucleophilic attack: the carbonyl carbon of the ester group.

Predict the nucleophilic acyl substitution mechanism, where the hydroxide ion attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate.

Consider the elimination of the leaving group (chloride ion) and the formation of the carboxylate anion as the final product.

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Key Concepts

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

Condensation Reactions

Condensation reactions involve the combination of two molecules with the loss of a small molecule, often water. In organic chemistry, these reactions are crucial for forming larger, more complex molecules from simpler ones. Understanding the mechanism of condensation is essential for predicting the products formed, especially when functional groups like -OH and -Cl are involved.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is significant for introducing various substituents, such as nitro or halogen groups, onto the aromatic system. Recognizing the reactivity of different substituents is vital for predicting the outcome of reactions involving aromatic compounds.

Functional Groups and Their Reactivity

Functional groups are specific groups of atoms within molecules that determine the chemical reactivity and properties of those molecules. In the given reaction, the presence of chlorine (Cl) and nitro (NO2) groups influences the reactivity of the compound. Understanding how different functional groups interact and their roles in chemical reactions is essential for predicting the products of organic reactions.