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

Previous problemNext problem

Problem 46e

Textbook Question

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

Verified step by step guidance

Step 1: Understand the concept of chirality. A molecule is chiral if it is not superimposable on its mirror image, meaning it lacks an internal plane of symmetry. Achiral molecules, on the other hand, have symmetry and are superimposable on their mirror images.

Step 2: Analyze the structure of the molecule provided. The molecule is a benzene ring substituted with three nitro groups (-NO2) at positions 1, 3, and 5.

Step 3: Check for symmetry in the molecule. The substituents are arranged symmetrically around the benzene ring, with identical groups (-NO2) at positions 1, 3, and 5. This indicates the presence of a plane of symmetry.

Step 4: Determine if the molecule can be superimposed on its mirror image. Due to the symmetrical arrangement of the substituents, the molecule is superimposable on its mirror image.

Step 5: Conclude the classification. Based on the analysis, the molecule is achiral because it has a plane of symmetry and is superimposable on its mirror image.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

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, resulting in two distinct forms known as enantiomers. This property is crucial in organic chemistry, especially in the context of pharmaceuticals, where different enantiomers can have different biological activities.

Achirality

Achirality describes molecules that are superimposable on their mirror images, meaning they do not have a chiral center. These molecules often possess a plane of symmetry or are symmetrical in structure. Understanding achirality is important for distinguishing between chiral and achiral substances, which can affect their chemical behavior and interactions.

Stereoisomerism

Stereoisomerism is a form of isomerism where molecules have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This includes both enantiomers (chiral) and diastereomers (not mirror images). Recognizing stereoisomers is essential for classifying molecules as chiral or achiral, as the arrangement of atoms can significantly influence their properties and reactivity.

Watch next

Master How and when to use the internal line of symmetry test. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Which of the following objects are chiral?

e. a wheelbarrow

f. a remote control device

g. a nail

h. screw

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

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

(d)

Multiple Choice

Which of the following molecules has a plane of symmetry?

Multiple Choice

Which of the following statements best describes a plane of symmetry in a molecule?

Multiple Choice

Which of the following statements best describes a plane of symmetry in a molecule?

Show more practices