Textbook Question
For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.
(c)
1
views
Ch.1 - Structure and Bonding
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 1, Problem 45e,f
For each pair of ions, determine which ion is more stable. Use resonance forms to explain your answers.
(e) 
(f) 
Verified step by step guidance1
Identify the ions in each pair: In set (e), we have two carbocations, and in set (f), we have two enolate ions.
For set (e), analyze the resonance stabilization: The carbocation adjacent to the double bond can be stabilized by resonance. Draw the resonance structures for each ion to see which one has more resonance forms.
For set (e), compare the resonance forms: The ion with more resonance forms is more stable because the positive charge is delocalized over a larger area, reducing the energy of the system.
For set (f), analyze the resonance stabilization: The enolate ion can be stabilized by resonance between the oxygen and the carbon atoms. Draw the resonance structures for each ion to see which one has more resonance forms.
For set (f), compare the resonance forms: The ion with more resonance forms is more stable because the negative charge is delocalized over a larger area, reducing the energy of the system.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
6mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Resonance
Resonance is a concept in organic chemistry that describes the delocalization of electrons in molecules. It occurs when a molecule can be represented by two or more valid Lewis structures, known as resonance forms. These forms contribute to the overall hybrid structure, which is more stable than any individual resonance form. Understanding resonance is crucial for predicting the stability of ions and molecules, as it allows for the distribution of charge and electron density.
Recommended video:
Guided course
03:04
Drawing Resonance Structures
Stability of Ions
The stability of ions is influenced by several factors, including charge distribution, electronegativity, and resonance. Generally, ions that can delocalize their charge through resonance are more stable than those that cannot. In the context of the question, comparing the stability of the two ions involves analyzing how effectively each ion can distribute its positive charge through resonance structures, which ultimately affects their reactivity and stability.
Recommended video:
3:39Metal Ion Catalysis Concept 1
Electrophilicity
Electrophilicity refers to the tendency of a species to accept electrons, making it a key factor in determining the reactivity of ions. In the case of positively charged ions, a more stable ion is typically less electrophilic because its positive charge is better stabilized through resonance. Understanding electrophilicity helps in predicting how these ions will interact with nucleophiles and other reactive species in organic reactions.
Recommended video:
Guided course
03:Nucleophile or Electrophile
Related Practice
Textbook Question
Use resonance structures to identify the areas of high and low electron density in the following compounds:
(a)
(b)
(c)
3
views
Textbook Question
Use resonance structures to identify the areas of high and low electron density in the following compounds:
g.
h.
2
views
Textbook Question
For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.
(a)
2
views
Textbook Question
Use resonance structures to identify the areas of high and low electron density in the following compounds:
i.
j.
1
views
Textbook Question
For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.
(b)
3
views