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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2:10 minutes

Problem 17c

Textbook Question

Identify the following substituted cycloalkanes as cis or trans.
(c)

Verified step by step guidance

Step 1: Understand the terms 'cis' and 'trans' in the context of substituted cycloalkanes. 'Cis' means that the substituents are on the same side of the cycloalkane ring, while 'trans' means that the substituents are on opposite sides of the ring.

Step 2: Examine the structure of the substituted cycloalkane provided in the problem. Identify the positions of the substituents on the ring and determine whether they are on the same side or opposite sides.

Step 3: Use wedge (solid triangle) and dash (dashed line) notation to determine the spatial orientation of the substituents. A wedge indicates that the substituent is coming out of the plane (towards you), while a dash indicates that the substituent is going into the plane (away from you).

Step 4: Compare the orientation of the substituents. If both substituents are represented by wedges or both by dashes, the molecule is 'cis'. If one substituent is a wedge and the other is a dash, the molecule is 'trans'.

Step 5: Assign the correct stereochemical descriptor (cis or trans) to the substituted cycloalkane based on your analysis in the previous steps.

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Key Concepts

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

Cis-Trans Isomerism

Cis-trans isomerism, also known as geometric isomerism, occurs in compounds with restricted rotation around a bond, typically in alkenes or cyclic structures. 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 spatial arrangement significantly affects the physical and chemical properties of the compounds.

Cycloalkanes

Cycloalkanes are saturated hydrocarbons with carbon atoms arranged in a ring structure. They can exhibit cis-trans isomerism when there are two or more substituents on the ring. The ability to classify these compounds as cis or trans depends on the relative positions of the substituents on the ring, which influences their stability and reactivity.

Substituent Priority

In determining whether a substituted cycloalkane is cis or trans, the priority of substituents is crucial. The Cahn-Ingold-Prelog priority rules help establish which substituents are considered higher priority based on atomic number and connectivity. This prioritization aids in accurately identifying the geometric configuration of the compound, which is essential for proper classification.

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Textbook Question

Name the following:

Textbook Question

Name the following:

Textbook Question

Draw the condensed structure for each of the following:

a. (Z)-1,3,5-tribromo-2-pentene

b. (Z)-3-methyl-2-heptene

c. (E)-1,2-dibromo-3-isopropyl-2-hexene

Textbook Question

Identify the following substituted cycloalkanes as cis or trans.

(a)

Textbook Question

For the compound 1-ethyl-3-isopropylcyclopentane,

(a) draw two different cis and two different trans isomers.

Textbook Question

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

b. using the E-Z nomenclature.

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.

c. 3-bromo-2-methylhex-3-ene

d. penta-1,3-diene

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.

a. 3-bromo-2-chloropent-2-ene

b. 3-ethylhexa-2,4-diene

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Identify the following substituted cycloalkanes as cis or trans. (c)

Key Concepts

Cis-Trans Isomerism

Cycloalkanes

Substituent Priority

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Identify the following substituted cycloalkanes as cis or trans.
(c)