Textbook Question
Draw the structure of each compound.
(i) tropylium chloride
(j) sodium cyclopentadienide
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Ch. 16 - Aromatic Compounds
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 16, Problem 26m,n
Draw the structure of each compound.
(m) p-toluenesulfonic acid
(n) o-xylene
Verified step by step guidance1
Step 1: Understand the structure of p-toluenesulfonic acid. It is derived from toluene, which is a benzene ring with a methyl group (-CH₃) attached. Additionally, it contains a sulfonic acid group (-SO₃H) attached to the para position (opposite the methyl group) on the benzene ring.
Step 2: Draw the benzene ring as a hexagon with alternating double bonds. This represents the aromatic structure of benzene.
Step 3: Add a methyl group (-CH₃) to one of the carbon atoms on the benzene ring. This is the toluene part of the molecule.
Step 4: Add a sulfonic acid group (-SO₃H) to the carbon atom directly opposite the methyl group (para position). This completes the structure of p-toluenesulfonic acid.
Step 5: For o-xylene, start with a benzene ring and add two methyl groups (-CH₃) to adjacent carbon atoms on the ring. This is the ortho (o-) configuration, where the substituents are on neighboring carbons.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the case of p-toluenesulfonic acid, the sulfonic acid group (-SO3H) is a key functional group that influences its acidity and reactivity. Understanding functional groups is essential for drawing and predicting the behavior of organic compounds.
Isomerism
Isomerism refers to the phenomenon where compounds have the same molecular formula but different structural arrangements or spatial orientations. o-Xylene is an example of a compound that exhibits isomerism, as it has two methyl groups attached to a benzene ring in different positions (ortho). Recognizing isomers is crucial for accurately representing and understanding the properties of organic compounds.
Structural Representation
Structural representation involves depicting the arrangement of atoms within a molecule, which can be done through various methods such as Lewis structures, condensed formulas, or skeletal formulas. For both p-toluenesulfonic acid and o-xylene, accurately drawing their structures is vital for visualizing their chemical properties and reactivity. Mastery of structural representation is fundamental in organic chemistry.
Related Practice
Textbook Question
Draw the structure of each compound.
(a) o-nitroanisole
(b) 2,4-dimethoxyphenol
(c) p-aminobenzoic acid
Textbook Question
Four pairs of compounds are shown. In each pair, one of the compounds reacts more quickly, or with a more favorable equilibrium constant, than the less conjugated system. In each case, explain the enhanced reactivity.
(a)
(b)
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Textbook Question
Four pairs of compounds are shown. In each pair, one of the compounds reacts more quickly, or with a more favorable equilibrium constant, than the less conjugated system. In each case, explain the enhanced reactivity.
(c)
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Textbook Question
The UV spectrum of 1-phenylprop-2-en-1-ol shows an intense absorption at 220 nm and a weaker absorption at 258 nm. When this compound is treated with dilute sulfuric acid, it rearranges to an isomer with an intense absorption at 250 nm and a weaker absorption at 290 nm. Suggest a structure for the isomeric product and propose a mechanism for its formation.
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Textbook Question
Name the following compounds:
(a)
(b)
(c)
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