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Ch.11 Introduction to Organic Chemistry: Hydrocarbons
Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 13th Edition
Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook
Chapter 11, Problem 73b

Explosives used in mining contain TNT, or trinitrotoluene.
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b. TNT is actually a mixture of isomers of trinitrotoluene. Draw the line-angle formulas for two other possible isomers.

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1
Understand the structure of TNT (trinitrotoluene). TNT is a benzene ring with three nitro groups (-NO₂) and one methyl group (-CH₃) attached. In the most common isomer, the methyl group is at position 1, and the nitro groups are at positions 2, 4, and 6 on the benzene ring.
Recall that isomers are compounds with the same molecular formula but different arrangements of atoms. For TNT, the molecular formula is C₇H₅N₃O₆. To create isomers, we can rearrange the positions of the nitro groups (-NO₂) on the benzene ring while keeping the methyl group (-CH₃) fixed.
Draw the first isomer: Place the methyl group (-CH₃) at position 1 on the benzene ring. Then, arrange the nitro groups at positions 2, 3, and 5. This creates a different spatial arrangement compared to the original TNT structure.
Draw the second isomer: Keep the methyl group (-CH₃) at position 1. Now, place the nitro groups at positions 2, 3, and 4. This is another unique arrangement of the nitro groups on the benzene ring.
Verify that both isomers have the same molecular formula (C₇H₅N₃O₆) as the original TNT structure. Ensure that the line-angle formulas clearly show the benzene ring, the methyl group, and the nitro groups in their respective positions for each isomer.

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Key Concepts

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

Isomers

Isomers are compounds that have the same molecular formula but different structural arrangements of atoms. This means they can exhibit different physical and chemical properties despite having the same number of each type of atom. In the case of trinitrotoluene (TNT), isomers arise from variations in the positioning of the nitro groups on the toluene ring.
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Line-Angle Formulas

Line-angle formulas, also known as skeletal formulas, are a shorthand representation of organic molecules. In these diagrams, vertices represent carbon atoms, and lines represent bonds between them. This method simplifies the drawing of complex structures, making it easier to visualize and communicate the arrangement of atoms in isomers like those of TNT.
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Trinitrotoluene (TNT)

Trinitrotoluene (TNT) is a well-known explosive compound characterized by its stability and effectiveness. Its chemical structure consists of a toluene molecule with three nitro groups attached, which can vary in their positions, leading to different isomers. Understanding TNT's structure is crucial for analyzing its properties and behavior in explosive applications.
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