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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5:07 minutes

Problem 1a,b,c

Textbook Question

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(a) PhCOOCH₂CH(CH₃)₂
(b) PhOCHO
(c) PhCH(CH₃)COOCH₃

Verified step by step guidance

Step 1: Analyze the structure in part (a), PhCOOCH2CH(CH3)2. This is an ester derived from benzoic acid (PhCOOH) and isopropyl alcohol (CH2CH(CH3)2). The common name is formed by naming the alcohol part first (isopropyl) followed by the acid part (benzoate). The IUPAC name is formed by naming the alcohol part as 'isopropyl' and the acid part as 'benzoate'.

Step 2: Examine the structure in part (b), PhOCHO. This is an aromatic aldehyde derivative where the benzene ring (Ph) is attached to a formyl group (-CHO). The common name is benzaldehyde. The IUPAC name is also benzaldehyde, as it is a simple aromatic aldehyde.

Step 3: Analyze the structure in part (c), PhCH(CH3)COOCH3. This is an ester derived from 2-phenylpropanoic acid (PhCH(CH3)COOH) and methanol (CH3OH). The common name is formed by naming the alcohol part first (methyl) followed by the acid part (2-phenylpropanoate). The IUPAC name is methyl 2-phenylpropanoate.

Step 4: For each structure, ensure you understand the naming conventions for carboxylic acid derivatives. Esters are named by identifying the alcohol-derived alkyl group first, followed by the acid-derived part with the suffix '-oate'. Aldehydes are named by replacing the '-e' in the parent alkane name with '-al'.

Step 5: Practice identifying functional groups and naming similar compounds to reinforce your understanding of carboxylic acid derivative nomenclature. Pay attention to the substituents and their positions on the parent chain or ring.

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Key Concepts

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

Carboxylic Acid Derivatives

Carboxylic acid derivatives are compounds that are derived from carboxylic acids by replacing the hydroxyl group (-OH) with another functional group. Common derivatives include esters, amides, anhydrides, and acyl chlorides. Understanding the structure and reactivity of these derivatives is crucial for naming and identifying them correctly.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for naming based on the structure of the molecule, including the longest carbon chain, functional groups, and substituents. Familiarity with these rules is essential for accurately naming carboxylic acid derivatives and distinguishing between common and systematic names.

Common Names vs. IUPAC Names

Common names are traditional names that may not follow systematic naming conventions, while IUPAC names are derived from a set of standardized rules. For carboxylic acid derivatives, common names often reflect historical usage or structural features, whereas IUPAC names provide a clear, unambiguous description of the compound's structure. Recognizing both naming conventions is important for effective communication in organic chemistry.

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