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

Test 2:Stereocenter Test

Organic Chemistry

5. Chirality

Test 2:Stereocenter Test

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Problem 16

Textbook Question

A molecule of the type shown here is discussed in greater detail in Section 6.5.1. Draw the mirror image. Is it superimposable? Switch the spatial orientation at both asymmetric centers. Have you generated a new molecule?

Verified step by step guidance

Step 1: Identify the asymmetric centers in the molecule. In the given structure, the two carbon atoms bonded to bromine (Br) and hydrogen (H) are asymmetric centers because they are bonded to four different groups.

Step 2: Draw the mirror image of the molecule. To do this, reflect the spatial orientation of the substituents (Br and H) at each asymmetric center across a vertical plane. For example, if Br is coming out of the plane (wedge), it will go into the plane (dash) in the mirror image, and vice versa for H.

Step 3: Determine if the mirror image is superimposable on the original molecule. Superimposability means that the mirror image can be aligned perfectly with the original molecule in three-dimensional space. If the molecule is chiral, the mirror image will not be superimposable.

Step 4: Switch the spatial orientation at both asymmetric centers. This involves interchanging the positions of the substituents (Br and H) at each asymmetric center. For example, if Br is on a wedge and H is on a dash, swap their positions.

Step 5: Analyze whether the new molecule generated by switching the spatial orientation at both asymmetric centers is identical to the original molecule or a different molecule. If the new molecule is not superimposable on the original, it is a stereoisomer (specifically, an enantiomer).

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Key Concepts

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

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image, much like how left and right hands are mirror images but cannot be perfectly aligned. Molecules with chirality typically contain one or more asymmetric centers, usually carbon atoms bonded to four different substituents, leading to two distinct enantiomers.

Asymmetric Centers

Asymmetric centers, or chiral centers, are atoms in a molecule that are bonded to four different groups or atoms. The presence of these centers is crucial for determining the chirality of a molecule, as they create the potential for two non-superimposable mirror images, known as enantiomers, which can exhibit different chemical properties and biological activities.

Stereoisomerism

Stereoisomerism is a form of isomerism where molecules have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This includes enantiomers, which are stereoisomers that are mirror images of each other, and diastereomers, which are not. Understanding stereoisomerism is essential for predicting the behavior and reactivity of chiral molecules in chemical reactions.

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Related Practice

Textbook Question

Which of the following has an asymmetric center?

CHBr₂Cl, BHFCl, CH₃CHCl₂, CHFBrCl, BeHCl

Textbook Question

Of all the possible cyclooctanes that have one chloro substituent and one methyl substituent, which ones do not have any asymmetric centers?

Textbook Question

Explain why compound A has two stereoisomers but compounds B and C exist as single compounds.

Textbook Question

The following four structures are naturally occurring optically active compounds. Star (*) the asymmetric carbon atoms in these structures.

Textbook Question

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

(e)

Textbook Question

Tetracycline is called a broad-spectrum antibiotic because it is active against a wide variety of bacteria. How many asymmetric centers does tetracycline have?

Textbook Question

a. How many asymmetric centers does the following compound have?

b. How many stereocenters does it have?

Textbook Question

The following compound has only one asymmetric center. Why then does it have four stereoisomers?

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