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

18. Aromaticity

Naming Benzene Rings

Organic Chemistry

18. Aromaticity

Naming Benzene Rings

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2:06 minutes

Problem 10d

Textbook Question

Draw a structure for each of the following:
d. m-chlorobenzonitrile

Verified step by step guidance

Step 1: Understand the name of the compound. 'm-chlorobenzonitrile' consists of a benzene ring with two substituents: a chlorine atom (chloro-) and a nitrile group (-C≡N). The 'm-' prefix indicates that these substituents are in a meta position relative to each other on the benzene ring.

Step 2: Draw the benzene ring. A benzene ring is a six-membered aromatic ring with alternating double bonds, represented as a hexagon with a circle inside or alternating double bonds.

Step 3: Place the nitrile group (-C≡N) on one of the carbons of the benzene ring. This will serve as the reference point for the meta position.

Step 4: Place the chlorine atom (Cl) on the carbon that is meta to the nitrile group. In the benzene ring, the meta position is two carbons away from the reference point, skipping one carbon in between.

Step 5: Verify the structure. Ensure that the benzene ring has six carbons, the nitrile group is correctly attached as -C≡N, and the chlorine atom is in the correct meta position relative to the nitrile group.

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Key Concepts

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

Benzonitrile Structure

Benzonitrile is an aromatic compound consisting of a benzene ring attached to a nitrile group (-C≡N). The structure features a carbon atom of the nitrile group triple-bonded to a nitrogen atom, which is directly connected to the benzene ring. Understanding this basic structure is essential for drawing derivatives like m-chlorobenzonitrile.

Meta Substitution in Aromatic Compounds

In aromatic chemistry, meta substitution refers to the positioning of substituents on a benzene ring. When a substituent is added to the benzene ring at the 1,3-positions relative to another substituent, it is termed 'meta.' For m-chlorobenzonitrile, the chlorine atom is positioned at the meta position relative to the nitrile group, which influences the compound's reactivity and properties.

Drawing Organic Structures

Drawing organic structures involves representing molecules using lines and symbols to depict atoms and bonds. In the case of m-chlorobenzonitrile, one must accurately illustrate the benzene ring, the nitrile group, and the chlorine substituent, ensuring correct bond angles and connectivity. Mastery of this skill is crucial for visualizing and understanding organic compounds.

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