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

5. Chirality

Constitutional Isomers vs. Stereoisomers

Organic Chemistry

5. Chirality

Constitutional Isomers vs. Stereoisomers

Previous problemNext problem

6:19 minutes

Problem 18b

Textbook Question

For the compound 1-ethyl-3-isopropylcyclopentane,

(b) What is the stereochemical relationship between the cis isomers?

Verified step by step guidance

Step 1: Identify the compound structure. The compound 1-ethyl-3-isopropylcyclopentane consists of a cyclopentane ring with an ethyl group at position 1 and an isopropyl group at position 3. The stereochemical relationship between the cis isomers depends on the spatial arrangement of these substituents.

Step 2: Define 'cis isomers.' Cis isomers occur when two substituents are on the same side of the cyclopentane ring. In this case, both the ethyl and isopropyl groups are positioned on the same face of the ring.

Step 3: Analyze the stereochemical relationship. Cis isomers of 1-ethyl-3-isopropylcyclopentane are diastereomers. Diastereomers are stereoisomers that are not mirror images of each other and have different physical and chemical properties.

Step 4: Examine the provided images. The images show two different cis configurations of the compound. The substituents are on the same side of the ring, but the spatial arrangement of the groups differs, confirming that they are diastereomers.

Step 5: Conclude the stereochemical relationship. The cis isomers of 1-ethyl-3-isopropylcyclopentane are diastereomers due to their distinct spatial arrangements while being on the same side of the ring.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 a double bond or 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 spatial arrangement can significantly affect the physical and chemical properties of the compounds.

Chirality

Chirality refers to the geometric property of a molecule having non-superimposable mirror images, much like left and right hands. A chiral molecule typically has a carbon atom bonded to four different substituents, creating two enantiomers. Understanding chirality is crucial for determining the stereochemical relationships between isomers, including whether they are identical, enantiomers, or diastereomers.

Stereochemical Relationships

Stereochemical relationships describe how different stereoisomers relate to one another in terms of their spatial arrangement. This includes identifying whether isomers are enantiomers (mirror images), diastereomers (not mirror images but different), or identical. Analyzing these relationships is essential for understanding the reactivity and properties of the compounds, especially in organic chemistry.

Watch next

Master Determining when molecules are different. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

For each of the following molecules, identify all stereocenters and draw all possible stereoisomers.

(b)

Textbook Question

Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice.Build molecular models of any of these examples that seem difficult to youe. Chlorocyclohexanef. Cis-1,2-dichlorocyclobutane

Textbook Question

Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice. Build molecular models of any of these examples that seem difficult to you.

(e) chlorocyclohexane

(f) cis-1,2-dichlorocyclobutane

Textbook Question

For each pair, give the relationship between the two compounds. Making models will be helpful.

(a) (2R,3S)-2,3-dibromohexane and (2S,3R)-2,3-dibromohexane

(b) (2R,3S)-2,3-dibromohexane and (2R,3R)-2,3-dibromohexane

Textbook Question

(a) Give the products expected when (+)@glyceraldehyde reacts with HCN.(b) What is the relationship between the products? How might they be separated?(c) Are the products optically active? Explain.

Textbook Question

(a) Give the products expected when (+)-glyceraldehyde reacts with HCN.

(b) What is the relationship between the products? How might they be separated?

Textbook Question