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

Naming Alkenes

Organic Chemistry

4. Alkanes and Cycloalkanes

Naming Alkenes

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2:19 minutes

Problem 26d,e,f

Textbook Question

Write structural formulas for the following compounds (includes both old- and new-style names).
(d) cyclohexylacetylene
(e) 5-methyl-3-octyne
(f) trans-3,5-dibromocyclodecyne

Verified step by step guidance

Step 1: Understand the naming conventions used in organic chemistry. Cyclohexylacetylene is a compound where a cyclohexyl group is attached to an acetylene group. The cyclohexyl group is a six-carbon ring, and acetylene is a two-carbon alkyne (triple bond).

Step 2: Draw the cyclohexyl group. This is a six-membered carbon ring, which can be represented as a hexagon. Each vertex of the hexagon represents a carbon atom.

Step 3: Attach the acetylene group to the cyclohexyl ring. Acetylene is represented as \( \text{C} \equiv \text{C} \), a linear structure with a triple bond between two carbon atoms. Connect one of the carbon atoms of the acetylene to one of the carbon atoms in the cyclohexyl ring.

Step 4: For 5-methyl-3-octyne, start by drawing the octane backbone, which is a straight chain of eight carbon atoms. Number the carbon atoms from 1 to 8.

Step 5: Add the substituents to the octane chain. At carbon 3, introduce a triple bond (alkyne), represented as \( \text{C} \equiv \text{C} \). At carbon 5, add a methyl group (\( \text{CH}_3 \)). Ensure the structure reflects the correct positioning of the triple bond and the methyl group.

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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 provides a standardized way to name compounds based on their structure, ensuring clear communication. Understanding IUPAC rules is essential for interpreting and writing chemical names, such as identifying the longest carbon chain, functional groups, and substituents.

Alkynes

Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond, characterized by the suffix '-yne' in their names. They are unsaturated compounds with the general formula CnH2n-2. Recognizing the presence of a triple bond is crucial for drawing structural formulas, as it affects the geometry and reactivity of the molecule, such as in cyclohexylacetylene and 5-methyl-3-octyne.

Cis-Trans Isomerism

Cis-trans isomerism, also known as geometric isomerism, occurs in alkenes and alkynes where restricted rotation around a double or triple bond leads to different spatial arrangements of substituents. In trans-3,5-dibromocyclodecyne, the 'trans' designation indicates that the bromine atoms are on opposite sides of the cyclodecyne ring, affecting the compound's physical and chemical properties.

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