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 1:Plane of Symmetry

Organic Chemistry

5. Chirality

Test 1:Plane of Symmetry

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2:27 minutes

Problem 13e-h

Textbook Question

Which of the following objects are chiral?
e. a wheelbarrow
f. a remote control device
g. a nail
h. screw

Verified step by step guidance

Step 1: Understand the concept of chirality. An object is chiral if it cannot be superimposed on its mirror image. This property is often associated with asymmetry.

Step 2: Analyze the wheelbarrow. A wheelbarrow typically has a symmetrical design, meaning its mirror image can be superimposed on the original. Therefore, it is not chiral.

Step 3: Examine the remote control device. Most remote controls are designed symmetrically for ergonomic purposes, making them superimposable on their mirror image. Thus, they are not chiral.

Step 4: Consider the nail. A standard nail is symmetrical along its axis, meaning its mirror image can be superimposed on the original. Hence, it is not chiral.

Step 5: Evaluate the screw. A screw often has a helical thread, which introduces asymmetry. Its mirror image cannot be superimposed on the original, making it chiral.

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Key Concepts

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

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 object typically has an asymmetric carbon atom, which is bonded to four different substituents. This concept is crucial in organic chemistry as it affects the behavior of molecules in biological systems and their interactions with other chiral molecules.

Symmetry

Symmetry in chemistry refers to the balanced and proportionate arrangement of parts in a molecule or object. An object is considered symmetric if it can be divided into two identical halves. Understanding symmetry helps in identifying chiral objects, as chiral items lack a plane of symmetry, while achiral items possess one.

Examples of Chiral and Achiral Objects

In organic chemistry, examples of chiral objects include molecules like amino acids and certain drugs, while achiral objects include symmetrical items like a wheelbarrow or a nail. Recognizing these examples aids in distinguishing between chiral and achiral substances, which is essential for understanding their chemical behavior and interactions.

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Related Practice

Textbook Question

Identify all planes of symmetry in the following molecules/conformations, if any.

(c)

Textbook Question

Identify all planes of symmetry in the following molecules/conformations, if any.

(f)

Textbook Question

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

(e)

Textbook Question

Which of the following objects are chiral?

a. a mug with DAD written to one side of the handle

b. a mug with MOM written to one side of the handle

c. a mug with DAD written opposite the handle

d. a mug with MOM written opposite the handle

Textbook Question

Draw structures for the following:

d. a chiral stereoisomer of 1,2-dibromocyclobutane

Textbook Question

Draw structures for the following:

e. two achiral stereoisomers of 3,4,5-trimethylheptane

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.

(h)

Textbook Question

Classify the following objects and molecules as chiral or achiral.

(e)

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