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

4. Alkanes and Cycloalkanes

IUPAC Naming

Organic Chemistry

4. Alkanes and Cycloalkanes

IUPAC Naming

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3:17 minutes

Problem 14c

Textbook Question

Draw the structure and give the systematic name for a compound with molecular formula C₅H₁₂ that has
(c) one tertiary hydrogen

Verified step by step guidance

Step 1: Understand the problem. The molecular formula C5H12 corresponds to an alkane (a saturated hydrocarbon). The problem specifies that the compound must have one tertiary hydrogen. A tertiary hydrogen is a hydrogen atom attached to a carbon that is itself bonded to three other carbons.

Step 2: Identify possible structures for C5H12. Since it is an alkane, the structure must follow the general formula CnH2n+2. For C5H12, there are three possible isomers: n-pentane, isopentane (2-methylbutane), and neopentane (2,2-dimethylpropane).

Step 3: Determine which structure contains a tertiary hydrogen. A tertiary hydrogen is only present in a structure where a carbon is bonded to three other carbons. Analyze each isomer: n-pentane has no tertiary carbons, neopentane has no tertiary hydrogens, but 2-methylbutane has one tertiary hydrogen on the central carbon.

Step 4: Draw the structure of 2-methylbutane. Start with a four-carbon chain (butane) and add a methyl group (-CH3) to the second carbon. Ensure that the structure satisfies the molecular formula C5H12 and includes one tertiary hydrogen.

Step 5: Provide the systematic name. The compound is named 2-methylbutane because the longest continuous chain has four carbons (butane), and a methyl group is attached to the second carbon. Verify that the structure matches the requirements of the problem.

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Key Concepts

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

Tertiary Hydrogen

A tertiary hydrogen is a hydrogen atom that is attached to a carbon atom, which in turn is bonded to three other carbon atoms. In organic chemistry, identifying tertiary hydrogens is crucial for understanding the reactivity and stability of molecules, particularly in reactions involving free radicals or carbocation formation.

Molecular Formula and Structure

The molecular formula C5H12 indicates that the compound contains five carbon atoms and twelve hydrogen atoms. This formula suggests that the compound is likely a saturated hydrocarbon, specifically an alkane, which can be represented by various structural isomers. Drawing the correct structure is essential for determining the compound's properties and systematic name.

Systematic Naming (IUPAC Nomenclature)

IUPAC nomenclature is a standardized system for naming chemical compounds based on their structure. For alkanes, the name is derived from the longest continuous carbon chain, with prefixes indicating the number of carbons and suffixes denoting the type of compound. Understanding this system is vital for accurately naming the compound with the given molecular formula and structural characteristics.

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