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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4:45 minutes

Problem 5d,e

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.
(d) 1,2-dichloropropane
(e)

Verified step by step guidance

Step 1: Analyze the structure of 1,2-dichloropropane. This molecule has a propane backbone with two chlorine atoms attached to the first and second carbon atoms. Check for symmetry by visualizing whether a plane can divide the molecule into two identical halves.

Step 2: Determine if 1,2-dichloropropane has an internal mirror plane. If the two halves of the molecule are not identical when divided by any plane, the molecule lacks a mirror plane. If it lacks a mirror plane, assess whether the molecule is chiral by checking for a non-superimposable mirror image.

Step 3: Analyze the structure of glyceraldehyde. This molecule has a central carbon atom (chiral center) bonded to four different groups: a hydroxyl group (-OH), a hydrogen atom (-H), a hydroxymethyl group (-CH2OH), and an aldehyde group (-CHO).

Step 4: Check for an internal mirror plane in glyceraldehyde. Since the central carbon is bonded to four different groups, the molecule cannot be divided into two identical halves by any plane, meaning it lacks an internal mirror plane.

Step 5: Conclude that glyceraldehyde is chiral because it has a chiral center (a carbon atom bonded to four different groups) and lacks an internal mirror plane of symmetry.

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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 at least one carbon atom bonded to four different substituents, resulting in two distinct enantiomers. Understanding chirality is crucial for determining the optical activity of compounds and their interactions in biological systems.

Symmetry and Mirror Planes

A mirror plane of symmetry is an imaginary plane that divides a molecule into two mirror-image halves. If a molecule possesses such a plane, it is considered achiral. Identifying symmetry elements, including mirror planes, is essential for assessing the stereochemical properties of a compound and determining its chirality.

Stereoisomerism

Stereoisomerism is a form of isomerism where molecules have the same molecular formula and connectivity but differ in the spatial arrangement of atoms. This includes enantiomers, which are non-superimposable mirror images, and diastereomers, which are not mirror images. Understanding stereoisomerism is vital for predicting the behavior and reactivity of organic compounds in chemical reactions.

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Master Three types of disubstituted cycloalkanes with a bite sized video explanation from Johnny

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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. (d) 1,2-dichloropropane(e)

Key Concepts

Chirality

Symmetry and Mirror Planes

Stereoisomerism

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