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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9:32 minutes

Problem 67h

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

Verified step by step guidance

Step 1: Begin by identifying the longest continuous carbon chain in the given structure. This chain will serve as the parent chain and determine the base name of the compound. Count the number of carbons in this chain to assign the correct alkane name.

Step 2: Number the parent chain starting from the end closest to the first substituent group. This ensures that the substituents are assigned the lowest possible locants (numbers).

Step 3: Identify and name all substituents attached to the parent chain. Substituents are named based on the number of carbons they contain, with the suffix '-yl' added to the alkane name (e.g., methyl, ethyl).

Step 4: Combine the substituent names with their respective locants and arrange them alphabetically. Ensure that the locants are correctly assigned based on the numbering of the parent chain. If the numbering results in a tie, the substituent that comes first alphabetically gets the lower number.

Step 5: Check the given name '5-ethyl-2-methylhexane' against the systematic naming rules. If the numbering of the substituents does not follow the lowest-locant rule, correct the name accordingly. For example, if the parent chain was misnumbered, renumber it and adjust the substituent locants to reflect the correct systematic name.

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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 for naming organic chemical compounds. It provides rules for identifying the longest carbon chain, naming substituents, and determining the correct order of naming based on the position of functional groups. Understanding these rules is essential for accurately naming compounds and avoiding misnomers.

Alkane Structure

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. Their general formula is CnH2n+2, where 'n' is the number of carbon atoms. Recognizing the structure of alkanes helps in identifying the correct parent chain and substituents when naming compounds.

Substituent Naming and Positioning

Substituents are groups attached to the main carbon chain and are named based on their structure. The position of each substituent is indicated by a number corresponding to the carbon atom it is attached to. Correctly identifying and numbering these substituents is crucial for accurate systematic naming.

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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

Draw the structures of the following compounds.

b. 5-(1,2,2-trimethylpropyl)nonane

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.

g. 3,3-dichlorooctane

Textbook Question

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

l. 5-isopropyldecane

Textbook Question

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

k. 3,4-dimethyloctane

Textbook Question

What is each compound's systematic name?

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