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

22. Carboxylic Acid Derivatives: NAS

Naming Esters

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Naming Esters

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4:09 minutes

Problem 42a,b,c

Textbook Question

Draw structures to correspond with the following common and systematic names:
(a) phenyl formate
(b) cyclohexyl benzoate
(c) cyclopentyl phenylacetate

Verified step by step guidance

Identify the functional group in each compound name. For esters, the name is derived from the alcohol and carboxylic acid components. The first part of the name corresponds to the alcohol-derived alkyl or aryl group, and the second part corresponds to the acid-derived portion.

For (a) phenyl formate: The 'phenyl' group is a benzene ring (C₆H₅), and 'formate' comes from formic acid (HCOOH). Replace the hydrogen in formic acid with the phenyl group to form the ester structure.

For (b) cyclohexyl benzoate: The 'cyclohexyl' group is a six-membered cycloalkane (C₆H₁₁), and 'benzoate' comes from benzoic acid (C₆H₅COOH). Replace the hydrogen in benzoic acid with the cyclohexyl group to form the ester structure.

For (c) cyclopentyl phenylacetate: The 'cyclopentyl' group is a five-membered cycloalkane (C₅H₉), and 'phenylacetate' comes from phenylacetic acid (C₆H₅CH₂COOH). Replace the hydrogen in phenylacetic acid with the cyclopentyl group to form the ester structure.

Draw the structures for each compound by combining the alcohol-derived group and the acid-derived group, ensuring the ester functional group (-COO-) is correctly formed in each case.

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Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, recognizing functional groups such as esters, phenols, and carboxylic acids is essential for drawing structures based on names. For example, phenyl formate contains a phenyl group and an ester functional group derived from formic acid.

Nomenclature Rules

IUPAC nomenclature provides a systematic way to name organic compounds based on their structure. Understanding the rules for naming compounds, including the identification of the longest carbon chain and the correct suffixes for functional groups, is crucial for translating names into chemical structures. For instance, 'benzoate' indicates the presence of a benzoic acid derivative, guiding the structure's construction.

Structural Representation

Structural representation involves depicting the arrangement of atoms within a molecule, including bonds and functional groups. This can be done through various methods such as Lewis structures, condensed formulas, or skeletal structures. Accurately representing the structures corresponding to names like cyclohexyl benzoate requires an understanding of how to illustrate cyclic and acyclic components effectively.

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