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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2:45 minutes

Problem 10b

Textbook Question

Draw skeletal structures for each pair of isomers in Problem 7
b.

Verified step by step guidance

Analyze the given structure: The compound contains a double bond (C=C) and a chlorine atom (Cl) attached to one of the carbons in the chain. This suggests the possibility of geometric (cis/trans) isomerism due to the double bond.

Understand the concept of geometric isomerism: Geometric isomers occur when there is restricted rotation around a double bond, and the substituents on the double-bonded carbons are arranged differently in space. For this compound, the chlorine atom and the ethyl group (CH2CH3) can be positioned either on the same side (cis) or opposite sides (trans) of the double bond.

Draw the skeletal structure for the cis isomer: In the cis isomer, the chlorine atom and the ethyl group are on the same side of the double bond. Represent the double bond as two parallel lines, and ensure the substituents are positioned correctly.

Draw the skeletal structure for the trans isomer: In the trans isomer, the chlorine atom and the ethyl group are on opposite sides of the double bond. Again, represent the double bond as two parallel lines, and position the substituents accordingly.

Verify the structures: Ensure that both skeletal structures maintain the correct connectivity of atoms and the correct placement of substituents relative to the double bond. Confirm that the cis and trans isomers are distinct and follow the rules of geometric isomerism.

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Key Concepts

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

Isomerism

Isomerism refers to the phenomenon where two or more compounds have the same molecular formula but different structural arrangements or spatial orientations. This can lead to distinct physical and chemical properties. The two main types of isomers are structural isomers, which differ in the connectivity of atoms, and stereoisomers, which have the same connectivity but differ in the spatial arrangement of atoms.

Skeletal Structures

Skeletal structures, also known as line-angle formulas, are a simplified way of representing organic molecules. In these diagrams, carbon atoms are represented by the ends and intersections of lines, while hydrogen atoms are often omitted for clarity. This method allows chemists to visualize the molecular framework quickly, focusing on functional groups and connectivity without cluttering the diagram with hydrogen atoms.

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. Common functional groups include hydroxyl (-OH), carboxyl (-COOH), and amino (-NH2) groups, and recognizing these groups is essential for understanding the behavior of isomers and their potential reactions.

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Textbook Question

Given the name, draw the structure of the following alkenes.

(b) ((Z)-1-cyclohexyl-2-methylhept-2-ene

Textbook Question

Draw the cis and trans isomers for the following:

a. 1-bromo-4-chlorocyclohexane

Textbook Question

Disregarding stereoisomers, draw the structures of all alkenes with molecular formula C₅H₁₀. Which ones can exist as cis–trans isomers?

Textbook Question

α-Farnesene is a dodecatetraene found in the waxy coating of apple skins. What is its systematic name? Include E and Z where necessary to indicate the configuration of the double bonds.

Textbook Question

Why does cis-2-butene have a higher boiling point than trans-2-butene?

Textbook Question

Imines can exist as stereoisomers. The isomers are named using the E,Z system of nomenclature (Section 4.2 ). The lone pair has the lowest priority.

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Draw the structure of each of the following compounds:

a. the (E)-hydrazone of benzaldehyde

b. the (Z)-oxime of propiophenone

Textbook Question

Draw and name all stereoisomers of 3-chlorohepta-2,4-diene

a. using the cis-trans nomenclature.

Textbook Question