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 3:Disubstituted Cycloalkanes

Organic Chemistry

5. Chirality

Test 3:Disubstituted Cycloalkanes

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4:39 minutes

Problem 5

Textbook Question

For each compound, determine whether the molecule has an internal mirror plane of symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the molecule. If the molecule does not have an internal mirror plane, determine whether the structure is chiral.a. Methaneb. cis-1,2-dibromocyclobutanec. trans-1,2-dibromocyclobutane

Verified step by step guidance

Identify the molecular geometry and symmetry elements of each compound.

For methane (CH₄), recognize that it is a tetrahedral molecule with high symmetry, including multiple mirror planes.

For cis-1,2-dibromocyclobutane, draw the cyclobutane ring in a three-dimensional perspective and place the bromine atoms on the same side of the ring. Check for a mirror plane that bisects the molecule.

For trans-1,2-dibromocyclobutane, draw the cyclobutane ring in a three-dimensional perspective and place the bromine atoms on opposite sides of the ring. Check for any mirror planes and assess chirality.

Determine the presence of a mirror plane for each compound and conclude whether each molecule is chiral or achiral based on the presence or absence of symmetry.

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Key Concepts

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

Symmetry in Molecules

Symmetry in molecules refers to the arrangement of atoms in a way that allows for a mirror image to be created. A molecule has an internal mirror plane of symmetry if it can be divided into two identical halves by a plane. This concept is crucial for determining the symmetry properties of a compound, which can influence its physical and chemical behavior.

Chirality

Chirality is a property of a molecule that makes it non-superimposable on its mirror image, much like left and right hands. A chiral molecule typically has no internal mirror plane of symmetry and often contains a carbon atom bonded to four different substituents. Understanding chirality is essential for predicting the optical activity of compounds and their interactions in biological systems.

Cyclic Compounds and Isomerism

Cyclic compounds, such as cyclobutane, can exhibit different forms of isomerism, including cis and trans configurations. The arrangement of substituents around the ring can affect the molecule's symmetry and chirality. Recognizing these isomeric forms is important for analyzing the spatial arrangement of atoms and determining the presence of symmetry elements in cyclic structures.

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