Domanda del libro di testo
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
e.
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Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of BenzeneProblema 7
Bruice 8th EditionCh. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of BenzeneProblema 7Capitolo 8, Problema 7
a. Predict the relative bond lengths of the three carbon–oxygen bonds in the carbonate ion.
b. What is the charge on each oxygen?
Guida verificata passo dopo passo1
Step 1: Analyze the structure of the carbonate ion (CO₃²⁻). The carbonate ion consists of one carbon atom bonded to three oxygen atoms. It has a resonance structure, meaning the electrons are delocalized across the molecule.
Step 2: Predict the relative bond lengths. Due to resonance, the three carbon–oxygen bonds in the carbonate ion are equivalent. The delocalization of electrons results in bond lengths that are intermediate between a single bond and a double bond. Therefore, all three C–O bonds have the same length.
Step 3: Determine the charge distribution. The carbonate ion has a total charge of -2. This charge is distributed across the three oxygen atoms due to resonance. Each oxygen atom carries a partial negative charge.
Step 4: Use formal charge calculations to confirm the charge on each oxygen. The formal charge on each oxygen can be calculated using the formula: Formal charge = (Valence electrons) - (Non-bonding electrons) - (Bonding electrons/2). For the carbonate ion, each oxygen atom has a formal charge of -2/3 due to the resonance structure.
Step 5: Summarize the findings. The three carbon–oxygen bonds in the carbonate ion are of equal length due to resonance, and each oxygen atom carries a partial negative charge, contributing to the overall -2 charge of the ion.
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Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In the case of the carbonate ion (CO3^2-), there are three resonance forms, each showing a different oxygen atom with a double bond to carbon. This delocalization leads to bond lengths that are intermediate between single and double bonds, affecting the overall stability and properties of the ion.
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03:04
Drawing Resonance Structures
Bond Lengths
Bond length refers to the distance between the nuclei of two bonded atoms. In the carbonate ion, the bond lengths of the carbon-oxygen bonds are influenced by the resonance structures. The C=O bond (double bond) is shorter than the C-O bond (single bond), resulting in all three C-O bonds being of equal length due to resonance, which is typically shorter than a single bond but longer than a double bond.
Video consigliato:
06:00Single bonds, double bonds, and triple bonds.
Formal Charge
Formal charge is a theoretical charge assigned to an atom in a molecule, calculated based on the number of valence electrons, the number of non-bonding electrons, and half the number of bonding electrons. In the carbonate ion, each oxygen atom carries a formal charge of -2/3 due to the distribution of electrons across the resonance structures, which helps to stabilize the ion and explains the overall -2 charge of the carbonate ion.
Video consigliato:
01:34Calculating formal and net charge.
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List the following in order of decreasing delocalization energy:
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Domanda del libro di testo
Which has the greater delocalization energy?
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Domanda del libro di testo
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
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Domanda del libro di testo
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
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Domanda del libro di testo
Which has the greater delocalization energy?
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