Textbook Question
Draw the structure of each compound.
(m) p-toluenesulfonic acid
(n) o-xylene
742
views
Ch. 16 - Aromatic Compounds
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 26a,b,c
Draw the structure of each compound.
(a) o-nitroanisole
(b) 2,4-dimethoxyphenol
(c) p-aminobenzoic acid
Verified step by step guidance1
Step 1: Understand the naming conventions for each compound. Organic compound names often provide information about the functional groups, substituents, and their positions on the parent structure. For example, 'o-' (ortho), 'p-' (para), and numerical prefixes indicate the positions of substituents on a benzene ring.
Step 2: For (a) o-nitroanisole: Start with a benzene ring as the parent structure. The prefix 'o-' (ortho) indicates that the substituents are adjacent to each other. Place a nitro group (-NO₂) on one carbon and a methoxy group (-OCH₃) on the adjacent carbon.
Step 3: For (b) 2,4-dimethoxyphenol: Begin with a benzene ring as the parent structure. The 'phenol' suffix indicates the presence of a hydroxyl group (-OH) attached to the benzene ring. Place the hydroxyl group at position 1. Then, add methoxy groups (-OCH₃) at positions 2 and 4 on the benzene ring.
Step 4: For (c) p-aminobenzoic acid: Start with a benzene ring as the parent structure. The 'p-' (para) prefix indicates that the substituents are opposite each other on the benzene ring. Place an amino group (-NH₂) on one carbon and a carboxylic acid group (-COOH) on the carbon directly opposite.
Step 5: Verify the structures by ensuring that all substituents are correctly placed according to the IUPAC naming rules and that the valency of each atom is satisfied. Draw the final structures clearly, showing all bonds and substituents.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
8mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Aromatic Compounds
Aromatic compounds are cyclic structures that follow Huckel's rule, having a planar configuration and a continuous ring of p-orbitals, allowing for delocalized pi electrons. This delocalization imparts unique stability and reactivity characteristics, making them essential in organic chemistry. Understanding the structure of aromatic compounds is crucial for drawing and interpreting the structures of compounds like o-nitroanisole and p-aminobenzoic acid.
Substituent Effects
Substituent effects refer to how different groups attached to a benzene ring influence its reactivity and the positions of further substitutions. Electron-donating groups (like -OCH3 in o-nitroanisole) activate the ring towards electrophilic substitution, while electron-withdrawing groups (like -NO2) deactivate it. Recognizing these effects is vital for accurately drawing the structures of compounds and predicting their chemical behavior.
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the compounds mentioned, -NO2 (nitro), -OCH3 (methoxy), and -COOH (carboxylic acid) are key functional groups that define their properties and reactivity. Identifying these groups is essential for understanding the overall structure and behavior of organic compounds.
Related Practice
Textbook Question
Draw the structure of each compound.
(i) tropylium chloride
(j) sodium cyclopentadienide
953
views
Textbook Question
Name the following compounds:
(a)
(b)
(c)
1223
views
1
rank
Textbook Question
Name the following compounds:
(d)
(e)
(f)
1136
views
1
rank
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.
1147
views
Textbook Question
Name the following compounds:
(a)
(b)
(c)
1420
views
1
rank