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 26i,j
Draw the structure of each compound.
(i) tropylium chloride
(j) sodium cyclopentadienide
Verified step by step guidance1
Understand the chemical nature of each compound: (i) Tropylium chloride is a salt composed of the tropylium cation (C7H7+) and a chloride anion (Cl-). The tropylium cation is aromatic and has a planar, cyclic structure with 7 carbon atoms and a positive charge. (j) Sodium cyclopentadienide is a salt composed of the cyclopentadienide anion (C5H5-) and a sodium cation (Na+). The cyclopentadienide anion is aromatic and has a planar, cyclic structure with 5 carbon atoms and a negative charge.
For (i) Tropylium chloride: Draw a heptagonal (7-sided) ring to represent the tropylium cation. Place alternating double and single bonds around the ring to indicate aromaticity. Add a positive charge (+) inside or near the ring to represent the cation. Then, add a chloride ion (Cl-) nearby to complete the salt structure.
For (j) Sodium cyclopentadienide: Draw a pentagonal (5-sided) ring to represent the cyclopentadienide anion. Place alternating double and single bonds around the ring to indicate aromaticity. Add a negative charge (-) inside or near the ring to represent the anion. Then, add a sodium ion (Na+) nearby to complete the salt structure.
Ensure that the structures are drawn with proper bond angles and symmetry to reflect the aromatic nature of both the tropylium cation and the cyclopentadienide anion. Aromaticity is confirmed by the Huckel rule (4n+2 π electrons, where n is an integer).
Label each structure clearly as (i) Tropylium chloride and (j) Sodium cyclopentadienide to avoid confusion. Verify that the charges on the cation and anion balance out to form neutral salts in both cases.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Tropylium Ion
The tropylium ion is a positively charged aromatic ion derived from toluene. It consists of a seven-membered carbon ring with a positive charge on one of the carbon atoms, making it a stable resonance structure. The aromatic nature of the ring contributes to its stability, allowing it to participate in various chemical reactions.
Cyclopentadiene
Cyclopentadiene is a five-membered cyclic compound with two double bonds. It is known for its ability to form a stable anion when deprotonated, which is crucial for understanding its reactivity. The cyclopentadienyl anion, formed from cyclopentadiene, is a key building block in organic synthesis and coordination chemistry.
Sodium Cyclopentadienide
Sodium cyclopentadienide is the sodium salt of the cyclopentadienyl anion, formed by deprotonating cyclopentadiene with sodium. This compound is a strong nucleophile and is often used in organic synthesis to form new carbon-carbon bonds. Its reactivity is largely due to the stability of the cyclopentadienyl anion, which can participate in various electrophilic substitution reactions.
Related Practice
Textbook Question
Draw the structure of each compound.
(a) o-nitroanisole
(b) 2,4-dimethoxyphenol
(c) p-aminobenzoic acid
1671
views
1
rank
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)
635
views
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