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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3:34 minutes

Problem 8b

Textbook Question

Draw the structures of the following compounds.
b. 5-(1,2,2-trimethylpropyl)nonane

Verified step by step guidance

Identify the parent chain: The parent chain is 'nonane', which means it is a straight chain alkane with 9 carbon atoms.

Locate the substituent: The substituent is '5-(1,2,2-trimethylpropyl)', which means it is attached to the 5th carbon of the nonane chain.

Understand the substituent structure: '1,2,2-trimethylpropyl' indicates a propyl group (3 carbon atoms) with three methyl groups attached. The numbering suggests that two methyl groups are attached to the second carbon and one methyl group is attached to the first carbon of the propyl group.

Draw the substituent: Start with a propyl group and add the methyl groups according to the given positions. The structure will have a central carbon with two methyl groups and another carbon with one methyl group.

Combine the structures: Attach the '1,2,2-trimethylpropyl' group to the 5th carbon of the nonane chain, ensuring that the overall structure maintains the correct connectivity and branching.

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Key Concepts

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

IUPAC Nomenclature

IUPAC nomenclature is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry. It ensures that each compound has a unique name, which describes its structure. Understanding the rules of IUPAC nomenclature is essential for interpreting and constructing chemical names and structures.

Alkane Structure

Alkanes are saturated hydrocarbons consisting of carbon and hydrogen atoms with single bonds. Their general formula is CnH2n+2. Recognizing the structure of alkanes, including linear and branched forms, is crucial for drawing and understanding compounds like nonane, which is a nine-carbon alkane.

Substituents in Organic Chemistry

Substituents are atoms or groups of atoms that replace hydrogen atoms in a hydrocarbon chain. In organic chemistry, identifying and correctly positioning substituents, such as the 1,2,2-trimethylpropyl group in the given compound, is vital for accurately drawing the molecular structure and understanding its chemical properties.

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Textbook Question

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly.

e. 2-cyclohexylbutane

f. 2,3-diethylcyclopentane

Textbook Question

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly.

c. 5-chloro-4-methylhexane

d. 2-dimethylbutane

Textbook Question

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly.

d. 4-isobutylheptane

e. 2-bromo-3-ethylbutane

f. 2,3-diethyl-5-isopropylheptane

Textbook Question

Draw the structures of the following compounds.

c. 3,3-diethyl-4-(2,2-dimethylpropyl)octane

Textbook Question

Provide IUPAC names for the following compounds.

(d)

(e)

(f)

Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

h. 5-ethyl-2-methylhexane

Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

g. 3,3-dichlorooctane

Textbook Question

Draw a condensed structure and a skeletal structure for each of the following:

l. 5-isopropyldecane

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