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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0:56 minutes

Problem 42h

Textbook Question

Draw structures to correspond with the following common and systematic names:
(h) γ-hydroxyvaleronitrile

Verified step by step guidance

Understand the name 'γ-hydroxyvaleronitrile': The name indicates that the compound is a nitrile (contains a -C≡N group) and has a hydroxy (-OH) group attached to the γ-carbon of a valeric acid derivative. Valeric acid is a five-carbon chain carboxylic acid, so the parent chain here will also have five carbons.

Identify the γ-carbon: In organic nomenclature, the α-carbon is the first carbon attached to the functional group (in this case, the nitrile group), the β-carbon is the second, and the γ-carbon is the third carbon away from the nitrile group.

Place the functional groups: Attach the nitrile group (-C≡N) to the first carbon of the chain. Then, place the hydroxy group (-OH) on the γ-carbon (the third carbon in the chain).

Complete the structure: Add hydrogens to the remaining carbons to satisfy the valency of carbon (four bonds per carbon atom). Ensure the structure is consistent with the molecular formula.

Verify the structure: Double-check that the structure matches the name 'γ-hydroxyvaleronitrile' by confirming the placement of the nitrile group, the hydroxy group, and the five-carbon chain.

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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 the case of γ-hydroxyvaleronitrile, the hydroxyl (-OH) group is a functional group that indicates the presence of alcohol, while the nitrile (-C≡N) group signifies the presence of a cyano group. Understanding these functional groups is essential for drawing the correct structure.

Nomenclature in Organic Chemistry

Nomenclature refers to the systematic naming of chemical compounds based on established rules. The name γ-hydroxyvaleronitrile indicates the structure's components: 'valeronitrile' suggests a five-carbon chain with a nitrile group, while 'γ-hydroxy' specifies that the hydroxyl group is attached to the gamma carbon (the fourth carbon in the chain). Familiarity with IUPAC nomenclature is crucial for accurately interpreting and constructing molecular structures.

Structural Representation of Molecules

Structural representation involves depicting the arrangement of atoms within a molecule, including bonds and functional groups. For γ-hydroxyvaleronitrile, one must illustrate the carbon backbone, the hydroxyl group, and the nitrile group correctly. Understanding how to represent these elements visually is vital for conveying the molecule's identity and properties effectively.

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