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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4:56 minutes

Problem 4(1)

Textbook Question

Draw skeletal structures for the compounds in Problem 3, including any cis–trans isomers.
1.

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 (geometric) isomerism is possible. Cis–trans isomerism occurs when there is restricted rotation around a double bond and two different groups are attached to each carbon of the double bond.

Draw the skeletal structure for each compound, representing carbon atoms as vertices and omitting hydrogen atoms bonded to carbons for simplicity. Use double lines for double bonds and ensure correct placement of 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 each structure clearly to distinguish between the isomers.

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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 that depict the arrangement of atoms without showing all the hydrogen atoms explicitly. In these diagrams, carbon atoms are represented by vertices or ends of lines, while bonds between them are shown as lines. This method allows chemists to visualize complex molecules more easily and focus on functional groups and connectivity.

Cis-Trans Isomerism

Cis-trans isomerism, also known as geometric isomerism, occurs in compounds with restricted rotation around a double bond or within a ring structure. In cis isomers, substituents are on the same side of the double bond or ring, while in trans isomers, they are on opposite sides. This difference in spatial arrangement can significantly affect the physical and chemical properties of the compounds, making it essential to identify both forms when drawing structures.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. They determine the properties and reactivity of organic compounds. Recognizing functional groups is crucial when drawing skeletal structures, as they influence the overall structure and behavior of the molecule, including its potential isomers.

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Related Practice

Textbook Question

Draw a structure for each compound (includes old and new names).

d. 1,3-cyclohexadiene

e. cycloocta-1,4-diene

f. (Z)-3-methyl-2-octene

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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: