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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3:22 minutes

Problem 48i

Textbook Question

Draw a structure for each of the following:
i. 3-methylbutanenitrile

Verified step by step guidance

Step 1: Understand the name of the compound. The name '3-methylbutanenitrile' indicates that the compound is a nitrile (contains a -C≡N group) and has a butane backbone (a four-carbon chain). The '3-methyl' prefix means there is a methyl (-CH₃) group attached to the third carbon of the main chain.

Step 2: Start by drawing the main chain. Draw a straight chain of four carbon atoms to represent the butane backbone.

Step 3: Add the nitrile group (-C≡N) to the first carbon of the chain. This is implied because the compound is named 'butanenitrile,' and the nitrile group is always at the end of the chain unless otherwise specified.

Step 4: Place the methyl group (-CH₃) on the third carbon of the chain. Number the carbon atoms in the chain starting from the carbon attached to the nitrile group to ensure proper placement.

Step 5: Verify the structure by ensuring that all carbon atoms have four bonds and that the functional groups and substituents are correctly placed according to the IUPAC name.

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Key Concepts

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

Nitriles

Nitriles are organic compounds that contain a cyano group (-C≡N), which consists of a carbon atom triple-bonded to a nitrogen atom. They are derived from carboxylic acids by replacing the -OH group with a -CN group. Nitriles are important in organic synthesis and can be converted into various functional groups, such as amines and carboxylic acids.

Alkyl Groups

Alkyl groups are hydrocarbon substituents derived from alkanes by removing one hydrogen atom. They are characterized by their carbon chain length and branching. In the case of 3-methylbutanenitrile, the '3-methyl' indicates a methyl group attached to the third carbon of a butane chain, which is crucial for determining the compound's structure and properties.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for identifying the longest carbon chain, numbering the chain, and naming substituents. Understanding IUPAC rules is essential for accurately interpreting and drawing chemical structures, such as recognizing that '3-methylbutanenitrile' indicates a butane backbone with a methyl group at the third position and a nitrile functional group.

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