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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4:04 minutes

Problem 8i

Textbook Question

Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.
(i)

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Identify the structure of cyclodeca-1,5-diene. It is a 10-membered carbon ring with two double bonds located at the 1st and 5th positions.

Determine if the compound can exhibit geometric isomerism. Geometric isomerism occurs in alkenes when there are different substituents on the carbon atoms involved in the double bond, allowing for cis-trans or E-Z isomerism.

For cyclodeca-1,5-diene, examine the double bonds. Each double bond in a ring can potentially show geometric isomerism if the ring is large enough to allow for different spatial arrangements.

Draw the possible geometric isomers. For each double bond, consider the spatial arrangement of the substituents around the double bond. In a ring, this can be more complex due to the ring's constraints.

Assign the E-Z configuration to each double bond. Use the Cahn-Ingold-Prelog priority rules to determine the priority of the substituents attached to the double-bonded carbons. Assign 'E' if the higher priority groups are on opposite sides and 'Z' if they are on the same side.

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Key Concepts

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

Geometric Isomerism

Geometric isomerism, also known as cis-trans isomerism, occurs in compounds with restricted rotation around a bond, typically a double bond or within a ring structure. This results in different spatial arrangements of substituents, leading to distinct isomers. Understanding geometric isomerism is crucial for identifying and drawing all possible isomers of a compound.

E-Z Nomenclature

The E-Z system is a method of naming geometric isomers based on the priority of substituents attached to the double-bonded carbons. 'E' (from the German 'entgegen') indicates that the higher priority groups are on opposite sides, while 'Z' (from 'zusammen') means they are on the same side. This system provides a clear and systematic way to name and differentiate isomers.

Cycloalkenes

Cycloalkenes are cyclic hydrocarbons containing one or more carbon-carbon double bonds. The presence of a ring structure can restrict rotation, making geometric isomerism possible. In cycloalkenes like cyclodeca-1,5-diene, the size of the ring and the position of the double bonds are critical factors in determining the possibility and number of geometric isomers.

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Related Practice

Textbook Question

Label each structure as Z, E, or neither.

(a)

(b)

(c)

(d)

Textbook Question

1. Determine which of the following compounds show cis-trans isomerism.

2. Draw and name the cis and trans (or Z and E) isomers of those that do.

e. 2,3-dimethylpent-2-ene

f. 3,4-dibromocyclopentene

Textbook Question

1. Determine which of the following compounds show cis-trans isomerism.

2. Draw and name the cis and trans (or Z and E) isomers of those that do.

a. hex-3-ene

b.buta-1,3-diene

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.

c. hex-3-ene

d. 1,1-dibromopropene

Textbook Question

Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.

(g)

(h)

Textbook Question

Some of the following examples can show geometric isomerism, and some cannot. For the ones that can, draw all the geometric isomers, and assign complete names using the E-Z system.

e. 3-ethyl-5-methyloct-3-ene

f. 3,7-dichloroocta-2,5-diene

Textbook Question

1. Determine which of the following compounds show cis-trans isomerism.

2. Draw and name the cis and trans (or Z and E) isomers of those that do.

c. hexa-2,4-diene

d. 3-methylpent-2-ene

Textbook Question

Give a correct name for each compound.

(c)

(d)

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