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

Cis vs Trans

Organic Chemistry

4. Alkanes and Cycloalkanes

Cis vs Trans

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3:22 minutes

Problem 4(2)

Textbook Question

Draw skeletal structures for the compounds in Problem 3, including any cis–trans isomers.
2.

Verified step by step guidance

Identify the compounds mentioned in Problem 3. If the problem refers to specific compounds, ensure you understand their molecular formulas, functional groups, and structural features.

For each compound, determine the main carbon chain (the longest continuous chain of carbon atoms) and identify any substituents or functional groups attached to it.

If the compound contains double bonds, assess whether cis–trans isomerism (geometric isomerism) is possible. This occurs when there are two different groups attached to each carbon of the double bond and the double bond is not at the end of the chain.

Draw the skeletal structure for each compound. Use zigzag lines to represent the carbon chain, omitting hydrogen atoms bonded to carbons for simplicity. Clearly indicate any functional groups or substituents.

For compounds with cis–trans isomerism, draw both the cis isomer (where substituents on the double-bonded carbons are on the same side) and the trans isomer (where substituents are on opposite sides). Label them appropriately.

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Key Concepts

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

Skeletal Structures

Skeletal structures, or line-angle formulas, are simplified representations of organic molecules where carbon atoms are implied at the ends and intersections of lines. This notation omits hydrogen atoms attached to carbons, making it easier to visualize complex molecules. Understanding how to draw and interpret these structures is essential for analyzing organic compounds.

Cis-Trans Isomerism

Cis-trans isomerism, a type of geometric isomerism, occurs in compounds with restricted rotation around a double bond or a ring structure. In cis isomers, substituents are on the same side, while in trans isomers, they are on opposite sides. Recognizing these configurations is crucial for understanding the physical and chemical properties of the compounds.

Functional Groups

Functional groups are specific groups of atoms within molecules that determine the chemical reactivity and properties of those molecules. Common functional groups include hydroxyl (-OH), carboxyl (-COOH), and amine (-NH2) groups. Identifying functional groups in skeletal structures helps predict the behavior of organic compounds in reactions.

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Related Practice

Textbook Question

Determine which compounds show cis-trans isomerism. Draw and label the isomers, using both the cis-trans and E-Z nomenclatures where applicable.

a. pent-1-ene

b. pent-2-ene

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Textbook Question

Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers.

b. 1-ethyl-3-methylcycloheptane

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Textbook Question

Draw the molecular orbital picture of trans-but-2-ene.

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Textbook Question

Draw skeletal structures for the compounds in Problem 3, including any cis–trans isomers.

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Textbook Question

a. Draw the condensed structures and give the systematic names for all the alkenes with molecular formula C₆H₁₂, ignoring stereoisomers. (Hint: There are 13.)

b. Which of the alkenes have E and Z isomers?

c. Which of the alkenes is the most stable?

d. Which of the alkenes is the least stable?

For those compounds that can exist as cis and trans isomers, draw and label the isomers.

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Textbook Question

Draw the cis and trans isomers for the following: