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

Chirality

Organic Chemistry

5. Chirality

Chirality

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Problem 12e

Textbook Question

Identify the following molecules as chiral or achiral. If chiral, draw the nonsuperimposable mirror image and verify its nonsuperimposability.
(e)

Verified step by step guidance

Step 1: Analyze the molecular structure provided in the image. The molecule is a benzene ring with two substituents: one methyl group and one ethyl group attached to adjacent carbon atoms on the ring.

Step 2: Determine if the molecule has a plane of symmetry. A molecule is achiral if it has a plane of symmetry, meaning one half of the molecule is a mirror image of the other half.

Step 3: Observe the substituents on the benzene ring. The methyl and ethyl groups are positioned such that the molecule has a plane of symmetry passing through the benzene ring and the substituents. This symmetry indicates that the molecule is achiral.

Step 4: Since the molecule is achiral, it does not have nonsuperimposable mirror images. Chiral molecules lack symmetry and have stereocenters, which this molecule does not possess.

Step 5: Conclude that the molecule is achiral based on the analysis of symmetry and the absence of stereocenters.

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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. A chiral molecule typically has a carbon atom bonded to four different substituents, leading to two distinct forms known as enantiomers. Understanding chirality is crucial for determining the optical activity of compounds, which is important in fields like pharmaceuticals.

Nonsuperimposable Mirror Images

Nonsuperimposable mirror images are pairs of structures that cannot be aligned perfectly, even when rotated or flipped. This concept is central to chirality, as chiral molecules possess such mirror images, known as enantiomers. To verify nonsuperimposability, one can use models or drawings to demonstrate that the two forms cannot be made to coincide.

Achirality

Achirality describes molecules that are superimposable on their mirror images, meaning they do not have a distinct left or right form. Achiral molecules often have a plane of symmetry or identical substituents around a central atom, which eliminates the possibility of forming enantiomers. Recognizing achiral structures is essential for distinguishing them from chiral ones in organic chemistry.

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Related Practice

Textbook Question

Classify the following objects and molecules as chiral or achiral.

(l)

Textbook Question

Identify the following molecules as chiral or achiral. If chiral, draw the nonsuperimposable mirror image and verify its nonsuperimposability.

(c)

Textbook Question

Classify the following objects and molecules as chiral or achiral.

(k)

Textbook Question

As we learned in Chapter 2, we don't need to show hydrogens bonded to carbons when drawing organic molecules using line-angle formulas. At asymmetric centers, however, we often show the hydrogen. Why? When might it be unnecessary to show the hydrogen at a chiral center?

Textbook Question

Classify the following objects and molecules as chiral or achiral.

(a) <IMAGE>

Textbook Question

Classify the following objects and molecules as chiral or achiral.

Textbook Question

Determine whether the following objects are chiral or achiral.

Textbook Question

The chiral BINAP ligand shown in Figure 8-8 contains no asymmetric carbon atoms. Explain how this ligand is chiral.

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