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

What is the Relationship Between Isomers?

Organic Chemistry

5. Chirality

What is the Relationship Between Isomers?

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8:44 minutes

Problem 90c(1,2,3,4)

Textbook Question

Identify
1. constitutional isomers
2. stereoisomers
3. cis–trans isomers
4. chiral compounds

Verified step by step guidance

Step 1: Constitutional isomers are compounds that have the same molecular formula but differ in the connectivity of their atoms. Analyze the structures provided to identify compounds with different connectivity, such as ethylcyclopentane and 1,1-dimethylcyclopentane, which differ in how the substituents are attached to the cyclopentane ring.

Step 2: Stereoisomers are compounds that have the same molecular formula and connectivity but differ in the spatial arrangement of atoms. Look for pairs of compounds where the substituents are arranged differently in 3D space, such as cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane.

Step 3: Cis–trans isomers are a specific type of stereoisomers that occur due to restricted rotation, often around a ring or double bond. Identify pairs of compounds where substituents are on the same side (cis) or opposite sides (trans) of the cyclopentane ring, such as cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane.

Step 4: Chiral compounds are molecules that are non-superimposable on their mirror images, often due to the presence of a chiral center (a carbon atom bonded to four different groups). Examine each structure to identify chiral centers, such as in trans-1,2-dimethylcyclopentane, where the spatial arrangement of substituents creates chirality.

Step 5: Summarize the findings by categorizing each compound into the appropriate groups (constitutional isomers, stereoisomers, cis–trans isomers, and chiral compounds) based on the analysis performed 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.

Constitutional Isomers

Constitutional isomers are compounds that have the same molecular formula but differ in the connectivity of their atoms. This means that the atoms are bonded together in different ways, leading to distinct structural formulas. For example, ethylcyclopentane and 1,1-dimethylcyclopentane both have the formula C7H14 but differ in how their carbon atoms are arranged.

Stereoisomers

Stereoisomers are compounds that have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This category includes cis-trans isomers and enantiomers. For instance, the cis- and trans- forms of 1,2-dimethylcyclopentane are stereoisomers because they have the same connectivity but differ in the orientation of their substituents around the ring.

Cis-Trans Isomers

Cis-trans isomers are a specific type of stereoisomer where the relative positions of substituents differ around a double bond or a ring structure. In cis isomers, similar groups are on the same side, while in trans isomers, they are on opposite sides. This distinction can significantly affect the physical and chemical properties of the compounds, as seen in the examples of cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane.

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Textbook Question

Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers?

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Textbook Question

Do the following structures represent identical compounds or a pair of enantiomers?

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Textbook Question

When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:

(a) Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetric carbon atom. (Using your models may be helpful.)

(b) Determine the relationship between the two stereoisomers you have drawn

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Textbook Question

What type of isomerism is indicated by each of the following pairs of molecules? Be as specific as possible.

(a)

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Textbook Question

Draw the mirror image of the following molecule. Then, using the mirror image generated, switch the spatial orientation at the asymmetric center. Is the final structure the enantiomer of the original? If not, what is it?

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Textbook Question

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

(h)

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Textbook Question

Make a model and draw a three-dimensional structure for each compound. Then draw the mirror image of your original structure and determine whether the mirror image is the same compound. Label each structure as being chiral or achiral, and label pairs of enantiomers.

(e)

(f)

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Textbook Question

For the molecules shown,

(i) count the number of stereocenters present and

(ii) draw all possible stereoisomers.

(iii) Identify the relationships between stereoisomers as enantiomers or diastereomers.

(a)

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