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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3:50 minutes

Problem 46h

Textbook Question

Classify the following objects and molecules as chiral or achiral.
(h)

Verified step by step guidance

Step 1: Understand the concept of chirality. A molecule or object is chiral if it cannot be superimposed on its mirror image. This typically occurs when a carbon atom is bonded to four different groups, creating a stereocenter. If the molecule has a plane of symmetry or can be superimposed on its mirror image, it is achiral.

Step 2: Examine the given object or molecule (h). Identify if there is a carbon atom (or other central atom) that is bonded to four distinct groups. If such a stereocenter exists, the molecule is likely chiral.

Step 3: Check for symmetry. Look for planes of symmetry or centers of symmetry in the molecule. If the molecule has a plane of symmetry, it is achiral, even if it has stereocenters.

Step 4: Consider the 3D structure of the molecule. Visualize or draw the molecule in three dimensions to determine if it can be superimposed on its mirror image. If it cannot, it is chiral; otherwise, it is achiral.

Step 5: Conclude the classification based on your analysis. If the molecule has no stereocenters or has symmetry, classify it as achiral. If it has stereocenters and lacks symmetry, classify it as chiral.

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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. These enantiomers can exhibit different optical activities, which is crucial in fields like pharmaceuticals.

Achirality

Achirality describes molecules that are superimposable on their mirror images, meaning they do not have a chiral center. Common examples include molecules with a plane of symmetry or those that are symmetrical in structure. Understanding achirality is essential for distinguishing between chiral and achiral substances in organic chemistry.

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 both enantiomers (chiral) and diastereomers (not mirror images). Recognizing stereoisomers is vital for classifying molecules as chiral or achiral and understanding their chemical behavior.

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Related Practice

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?

Textbook Question

The stereoisomer of cholesterol found in nature is shown here.

a. How many asymmetric centers does cholesterol have?

b. What is the maximum number of stereoisomers that cholesterol can have?

Textbook Question

How many stereogenic double bonds are in octa-1,3,5-triene? How many stereocenters are there? Draw and name the four stereoisomers of octa-1,3,5-triene.

Textbook Question

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

(f)

Multiple Choice

Which of the following atoms are stereocenters?

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?

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