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 Nitriles

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Naming Nitriles

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3:55 minutes

Problem 1f

Textbook Question

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.
(f) CH₃CH(OH)CH₂CN

Verified step by step guidance

Step 1: Analyze the problem and identify the functional groups in each compound. Carboxylic acid derivatives include esters, amides, and anhydrides. For each compound, locate the functional group and any substituents attached to the main chain or aromatic ring.

Step 2: For compound (a) PhCOOCH2CH(CH3)2, identify the ester functional group. The aromatic ring (Ph) is attached to the carbonyl group, and the alkyl group is isopropylmethyl. Use the common naming convention (alkyl group + benzoate) and the IUPAC naming convention (alkyl benzenecarboxylate).

Step 3: For compound (b) PhOCHO, identify the aldehyde functional group attached to the aromatic ring. The common name is benzaldehyde, and the IUPAC name is benzenecarbaldehyde.

Step 4: For compound (c) PhCH(CH3)COOCH3, identify the ester functional group. The aromatic ring (Ph) is attached to a chain with a methyl substituent and a methoxy group. Use the common naming convention (alkyl group + phenylacetate) and the IUPAC naming convention (methyl 2-phenylpropanoate).

Step 5: For compound (d) PhNHCOCH2CH(CH3)2, identify the amide functional group. The aromatic ring (Ph) is attached to the nitrogen atom, and the alkyl group is isopropylmethyl. Use the common naming convention (alkyl group + benzamide) and the IUPAC naming convention (N-phenyl-2-methylpropanamide).

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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 include compounds such as esters, amides, and anhydrides, which are derived from carboxylic acids. They retain the carboxyl functional group (–COOH) but have different substituents replacing the hydroxyl group (–OH). Understanding the structure and reactivity of these derivatives is crucial for naming and synthesizing organic compounds.

IUPAC Nomenclature

The International Union of Pure and Applied Chemistry (IUPAC) nomenclature provides a systematic method for naming organic compounds. It involves identifying the longest carbon chain, determining the functional groups, and applying specific rules for naming based on the structure. Familiarity with IUPAC rules is essential for accurately naming carboxylic acid derivatives and other organic molecules.

Common Names vs. IUPAC Names

Common names are often simpler and more widely recognized names for compounds, while IUPAC names follow a standardized set of rules. For example, acetic acid is the common name for ethanoic acid. Understanding both naming conventions is important for effective communication in organic chemistry, as different contexts may require different naming styles.

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