Write equations describing the additionelimination mechanism for the reaction of hexafluorobenzene with sodium methoxide, clearly showing the structure of the rate-determining intermediate.
Read moreTable of Contents
1
Structure Determines Properties
1.1
Atoms, Electrons, and Orbitals
1.10
The Shapes of Some Simple Molecules
1.11
Molecular Dipole Moments
1.12
Curved Arrows and Chemical Reactions
1.13
Acids and Bases: The BrnstedLowry View
1.14
How Structure Affects Acid Strength
1.15
AcidBase Equilibria
1.16
Lewis Acids and Lewis Bases
1.2
Ionic Bonds
1.3
Covalent Bonds, Lewis Formulas, and the Octet Rule
1.4
Double Bonds and Triple Bonds
1.5
Polar Covalent Bonds, Electronegativity, and Bond Dipoles
1.6
Formal Charge
1.7
Structural Formulas of Organic Molecules
1.8
Resonance
1.9
Sulfur and Phosphorus-Containing Organic Compounds and the Octet Rule
2
Alkanes and Cycloalkanes: Introduction to Hydrocarbons
2.12
Higher n-Alkanes
2.13
The C5H12 Isomers
2.14
IUPAC Nomenclature of Unbranched Alkanes
2.15
Applying the IUPAC Rules: The Names of the C6H14 Isomers
2.16
Alkyl Groups
2.17
IUPAC Names of Highly Branched Alkanes
2.18
Cycloalkane Nomenclature
2.19
Sources of Alkanes and Cycloalkanes
2.20
Physical Properties of Alkanes and Cycloalkanes
2.21
Chemical Properties: Combustion of Alkanes
2.22
OxidationReduction in Organic Chemistry
2.4
Bonding in H2: The Molecular Orbital Model
2.7
Bonding in Ethane
2.8
sp2 Hybridization and Bonding in Ethylene
2.9
sp Hybridization and Bonding in Acetylene
3
Alkanes and Cycloalkanes: Conformations and cistrans Stereoisomers
3.1
Conformational Analysis of Ethane
3.10
Conformational Analysis of Monosubstituted Cyclohexanes
3.11
Disubstituted Cycloalkanes: cistrans Stereoisomers
3.12
Conformational Analysis of Disubstituted Cyclohexanes
3.14
Polycyclic Ring Systems
3.15
Heterocyclic Compounds
3.2
Conformational Analysis of Butane
3.3
Conformations of Higher Alkanes
3.5
Small Rings: Cyclopropane and Cyclobutane
3.8
Axial and Equatorial Bonds in Cyclohexane
4
Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms
4.1
Functional Groups
4.11
Reaction of Methyl and Primary Alcohols with Hydrogen Halides: The SN2 Mechanism
4.12
Other Methods for Converting Alcohols to Alkyl Halides
4.15
Structure and Stability of Free Radicals
4.16
Mechanism of Methane Chlorination
4.17
Halogenation of Higher Alkanes
4.2
IUPAC Nomenclature of Alkyl Halides
4.3
IUPAC Nomenclature of Alcohols
4.4
Classes of Alcohols and Alkyl Halides
4.5
Bonding in Alcohols and Alkyl Halides
4.6
Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces
4.7
Preparation of Alkyl Halides from Alcohols and Hydrogen Halides
4.8
Reaction of Alcohols with Hydrogen Halides: The SN1 Mechanism
4.9
Structure, Bonding, and Stability of Carbocations
5
Structure and Preparation of Alkenes: Elimination Reactions
5.1
Alkene Nomenclature
5.10
Regioselectivity in Alcohol Dehydration: The Zaitsev Rule
5.11
Stereoselectivity in Alcohol Dehydration
5.12
The E1 and E2 Mechanisms of Alcohol Dehydration
5.13
Rearrangements in Alcohol Dehydration
5.14
Dehydrohalogenation of Alkyl Halides
5.15
The E2 Mechanism of Dehydrohalogenation of Alkyl Halides
5.16
Anti Elimination in E2 Reactions: Stereoelectronic Effects
5.17
Isotope Effects and the E2 Mechanism
5.18
The E1 Mechanism of Dehydrohalogenation of Alkyl Halides
5.2
Structure and Bonding in Alkenes
5.3
Isomerism in Alkenes
5.4
Naming Stereoisomeric Alkenes by the EZ Notational System
5.5
Physical Properties of Alkenes
5.6
Relative Stabilities of Alkenes
5.7
Cycloalkenes
5.9
Dehydration of Alcohols
6
Addition Reactions of Alkenes
6.1
Hydrogenation of Alkenes
6.10
Addition of Halogens to Alkenes
6.11
Epoxidation of Alkenes
6.12
Ozonolysis of Alkenes
6.13
Free-Radical Addition of Hydrogen Bromide to Alkenes
6.14
Free-Radical Polymerization of Alkenes
6.15
Introduction to Organic Chemical Synthesis: Retrosynthetic Analysis
6.2
Stereochemistry of Alkene Hydrogenation
6.3
Heats of Hydrogenation
6.4
Electrophilic Addition of Hydrogen Halides to Alkenes
6.5
Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes
6.6
Acid-Catalyzed Hydration of Alkenes
6.7
Thermodynamics of AdditionElimination Equilibria
6.8
HydroborationOxidation of Alkenes
7
Chirality
7.10
Reactions That Create a Chirality Center
7.11
Chiral Molecules with Two Chirality Centers
7.12
Achiral Molecules with Two Chirality Centers
7.13
Molecules with Multiple Chirality Centers
7.14
Reactions That Produce Diastereomers
7.15
Resolution of Enantiomers
7.2
The Chirality Center
7.3
Symmetry in Achiral Structures
7.4
Optical Activity
7.5
Absolute and Relative Configuration
7.6
The CahnIngoldPrelog RS Notational System
7.7
Fischer Projections
7.8
Properties of Enantiomers
7.9
The Chirality Axis
8
Nucleophilic Substitution
8.1
Functional Group Transformation by Nucleophilic Substitution
8.10
Substitution and Elimination as Competing Reactions
8.11
Nucleophilic Substitution of Alkyl Sulfonates
8.12
Nucleophilic Substitution and Retrosynthetic Analysis
8.2
Relative Reactivity of Halide Leaving Groups
8.3
The SN2 Mechanism of Nucleophilic Substitution
8.4
Steric Effects and SN2 Reaction Rates
8.6
The SN1 Mechanism of Nucleophilic Substitution
8.7
Stereochemistry of SN1 Reactions
8.8
Carbocation Rearrangements in SN1 Reactions
8.9
Effect of Solvent on the Rate of Nucleophilic Substitution
9
Alkynes
9.1
Sources of Alkynes
9.10
MetalAmmonia Reduction of Alkynes
9.11
Addition of Hydrogen Halides to Alkynes
9.12
Hydration of Alkynes
9.14
Ozonolysis of Alkynes
9.15
Alkynes in Synthesis and Retrosynthesis
9.2
Nomenclature
9.4
Structure and Bonding in Alkynes: sp Hybridization
9.5
Acidity of Acetylene and Terminal Alkynes
9.6
Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes
9.7
Preparation of Alkynes by Elimination Reactions
9.9
Hydrogenation of Alkynes
10
Conjugation in Alkadienes and Allylic Systems
10.1
The Allyl Group
10.10
Addition of Hydrogen Halides to Conjugated Dienes
10.11
Halogen Addition to Dienes
10.12
The DielsAlder Reaction
10.13
Retrosynthetic Analysis and the DielsAlder Reaction
10.2
SN1 and SN2 Reactions of Allylic Halides
10.3
Allylic Free-Radical Halogenation
10.4
Allylic Anions
10.5
Classes of Dienes: Conjugated and Otherwise
10.6
Relative Stabilities of Dienes
10.7
Bonding in Conjugated Dienes
10.8
Bonding in Allenes
10.9
Preparation of Dienes
11
Arenes and Aromaticity
11.10
Benzylic Free-Radical Halogenation
11.11
Benzylic Anions
11.12
Oxidation of Alkylbenzenes
11.13
Alkenylbenzenes
11.15
The Birch Reduction
11.16
Benzylic Side Chains and Retrosynthetic Analysis
11.17
Cyclobutadiene and Cyclooctatetraene
11.18
Hckels Rule
11.19
Annulenes
11.2
The Structure of Benzene
11.20
Aromatic Ions
11.21
Heterocyclic Aromatic Compounds
11.22
Heterocyclic Aromatic Compounds and Hckels Rule
11.3
The Stability of Benzene
11.5
Substituted Derivatives of Benzene and Their Nomenclature
11.6
Polycyclic Aromatic Hydrocarbons
11.8
The Benzyl Group
11.9
Nucleophilic Substitution in Benzylic Halides
12
Electrophilic and Nucleophilic Aromatic Substitution
12.10
Rate and Regioselectivity in the Nitration of Toluene
12.11
Rate and Regioselectivity in the Nitration of (Trifluoromethyl)benzene
12.12
Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents
12.13
Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents
12.14
Substituent Effects in Electrophilic Aromatic Substitution: Halogens
12.15
Multiple Substituent Effects
12.16
Retrosynthetic Analysis and the Synthesis of Substituted Benzenes
12.17
Substitution in Naphthalene
12.18
Substitution in Heterocyclic Aromatic Compounds
12.19
Nucleophilic Aromatic Substitution
12.2
Mechanistic Principles of Electrophilic Aromatic Substitution
12.20
The AdditionElimination Mechanism of Nucleophilic Aromatic Substitution
12.21
Related Nucleophilic Aromatic Substitutions
12.3
Nitration of Benzene
12.4
Sulfonation of Benzene
12.5
Halogenation of Benzene
12.6
FriedelCrafts Alkylation of Benzene
12.7
FriedelCrafts Acylation of Benzene
12.8
Synthesis of Alkylbenzenes by AcylationReduction
13
Spectroscopy
13.11
Complex Splitting Patterns
13.12
1 H NMR Spectra of Alcohols
13.14
13C NMR Spectroscopy
13.15
13C Chemical Shifts
13.16
13C NMR and Peak Intensities
13.18
Using DEPT to Count Hydrogens
13.20
Introduction to Infrared Spectroscopy
13.21
Infrared Spectra
13.22
Characteristic Absorption Frequencies
13.23
Ultraviolet-Visible Spectroscopy
13.24
Mass Spectrometry
13.25
Molecular Formula as a Clue to Structure
13.3
Introduction to 1 H NMR Spectroscopy
13.4
Nuclear Shielding and 1 H Chemical Shifts
13.5
Effects of Molecular Structure on 1 H Chemical Shifts
13.6
Interpreting 1 H NMR Spectra
13.7
SpinSpin Splitting and 1 H NMR
13.8
Splitting Patterns: The Ethyl Group
14
Organometallic Compounds
14.1
Organometallic Nomenclature
14.10
Organocopper Reagents
14.11
Palladium-Catalyzed Cross-Coupling
14.12
Homogeneous Catalytic Hydrogenation
14.13
Olefin Metathesis
14.3
Preparation of Organolithium and Organomagnesium Compounds
14.4
Organolithium and Organomagnesium Compounds as Brnsted Bases
14.5
Synthesis of Alcohols Using Grignard and Organolithium Reagents
14.7
Retrosynthetic Analysis and Grignard and Organolithium Reagents
14.8
An Organozinc Reagent for Cyclopropane Synthesis
14.9
Transition-Metal Organometallic Compounds
15
Alcohols, Diols, and Thiols
15.10
Biological Oxidation of Alcohols
15.11
Oxidative Cleavage of Vicinal Diols
15.12
Thiols
15.2
Preparation of Alcohols by Reduction of Aldehydes and Ketones
15.4
Preparation of Alcohols from Epoxides
15.5
Preparation of Diols
15.7
Conversion of Alcohols to Ethers
15.8
Esterification
15.9
Oxidation of Alcohols
16
Ethers, Epoxides, and Sulfides
16.1
Nomenclature of Ethers, Epoxides, and Sulfides
16.10
Conversion of Vicinal Halohydrins to Epoxides
16.11
Reactions of Epoxides with Anionic Nucleophiles
16.12
Acid-Catalyzed Ring Opening of Epoxides
16.14
Preparation of Sulfides
16.15
Oxidation of Sulfides: Sulfoxides and Sulfones
16.16
Alkylation of Sulfides: Sulfonium Salts
16.17
Spectroscopic Analysis of Ethers, Epoxides, and Sulfides
16.2
Structure and Bonding in Ethers and Epoxides
16.3
Physical Properties of Ethers
16.4
Crown Ethers
16.5
Preparation of Ethers
16.6
The Williamson Ether Synthesis
16.8
Acid-Catalyzed Cleavage of Ethers
16.9
Preparation of Epoxides
17
Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group
17.1
Nomenclature
17.10
Reaction with Primary Amines: Imines
17.11
Reaction with Secondary Amines: Enamines
17.12
The Wittig Reaction
17.13
Stereoselective Addition to Carbonyl Groups
17.3
Physical Properties
17.4
Sources of Aldehydes and Ketones
17.6
Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones
17.7
Cyanohydrin Formation
17.8
Reaction with Alcohols: Acetals and Ketals
17.9
Acetals and Ketals as Protecting Groups
18
Carboxylic Acids
18.1
Carboxylic Acid Nomenclature
18.11
Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents
18.12
Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles
18.4
Acidity of Carboxylic Acids
18.5
Substituents and Acid Strength
18.6
Ionization of Substituted Benzoic Acids
18.7
Salts of Carboxylic Acids
18.9
Carbonic Acid
19
Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
19.1
Nomenclature of Carboxylic Acid Derivatives
19.10
Reaction of Esters with Ammonia and Amines
19.11
Reaction of Esters with Grignard and Organolithium Reagents and Lithium Aluminum Hydride
19.12
Amides
19.13
Hydrolysis of Amides
19.14
Lactams
19.15
Preparation of Nitriles
19.16
Hydrolysis of Nitriles
19.17
Addition of Grignard Reagents to Nitriles
19.2
Structure and Reactivity of Carboxylic Acid Derivatives
19.3
Nucleophilic Acyl Substitution Mechanisms
19.4
Nucleophilic Acyl Substitution in Acyl Chlorides
19.5
Nucleophilic Acyl Substitution in Acid Anhydrides
19.8
Acid-Catalyzed Ester Hydrolysis
19.9
Ester Hydrolysis in Base: Saponification
20
Enols and Enolates
20.1
Enol Content and Enolization
20.2
Enolates
20.3
The Aldol Condensation
20.4
Mixed and Directed Aldol Reactions
20.5
Acylation of Enolates: The Claisen and Related Condensations
20.6
Alkylation of Enolates: The Acetoacetic Ester and Malonic Ester Syntheses
20.7
The Haloform Reaction
20.8
Conjugation Effects in ,-Unsaturated Aldehydes and Ketones
21
Amines
21.1
Amine Nomenclature
21.10
Reductive Amination
21.13
The Hofmann Elimination
21.14
Electrophilic Aromatic Substitution in Arylamines
21.15
Nitrosation of Alkylamines
21.17
Synthetic Transformations of Aryl Diazonium Salts
21.18
Azo Coupling
21.2
Structure and Bonding
21.4
Basicity of Amines
21.7
Preparation of Amines by Alkylation of Ammonia
21.8
The Gabriel Synthesis of Primary Alkylamines
21.9
Preparation of Amines by Reduction
22
Phenols
22.1
Nomenclature
22.11
Preparation of Aryl Ethers
22.13
Claisen Rearrangement of Allyl Aryl Ethers
22.3
Physical Properties
22.4
Acidity of Phenols
22.5
Substituent Effects on the Acidity of Phenols
22.6
Sources of Phenols
22.8
Reactions of Phenols: Electrophilic Aromatic Substitution
22.9
Acylation of Phenols
23
Carbohydrates
23.10
Ketoses
23.11
Deoxy Sugars
23.12
Amino Sugars
23.14
Glycosides: The Fischer Glycosidation
23.15
Disaccharides
23.17
Application of Familiar Reactions to Monosaccharides
23.18
Oxidation of Monosaccharides
23.2
Fischer Projections and D,L Notation
23.20
Glycobiology
23.3
The Aldotetroses
23.4
Aldopentoses and Aldohexoses
23.6
Cyclic Forms of Carbohydrates: Furanose Forms
23.7
Cyclic Forms of Carbohydrates: Pyranose Forms
23.8
Mutarotation
23.9
Carbohydrate Conformation: The Anomeric Effect
24
Lipids
24.10
The Pathway from Acetate to Isopentenyl Diphosphate
24.11
Steroids: Cholesterol
24.12
Vitamin D
24.16
Carotenoids
24.2
Fats, Oils, and Fatty Acids
24.3
Fatty Acid Biosynthesis
24.4
Phospholipids
24.5
Waxes
24.6
Prostaglandins
24.7
Terpenes: The Isoprene Rule
24.9
CarbonCarbon Bond Formation in Terpene Biosynthesis
25
Amino Acids, Peptides, and Proteins
25.1
Classification of Amino Acids
25.10
Partial Hydrolysis and End Group Analysis
25.12
Edman Degradation and Automated Sequencing of Peptides
25.15
Peptide Bond Formation
25.16
Solid-Phase Peptide Synthesis: The Merrifield Method
25.17
Secondary Structures of Peptides and Proteins
25.18
Tertiary Structure of Polypeptides and Proteins
25.2
Stereochemistry of Amino Acids
25.3
AcidBase Behavior of Amino Acids
25.4
Synthesis of Amino Acids
25.5
Reactions of Amino Acids
25.6
Some Biochemical Reactions of Amino Acids
25.7
Peptides
25.9
Amino Acid Analysis
26
Nucleosides, Nucleotides, and Nucleic Acids
26.1
Pyrimidines and Purines
26.10
Phosphodiesters, Oligonucleotides, and Polynucleotides
26.12
Protein Biosynthesis
26.13
AIDS
26.2
Nucleosides
26.3
Nucleotides
26.5
ATP and Bioenergetics
26.7
Nucleic Acids
26.9
Tertiary Structure of DNA: Supercoils
27
Synthetic Polymers
27.11
Polyamides
27.12
Polyesters
27.13
Polycarbonates
27.14
Polyurethanes
27.2
Polymer Nomenclature
27.3
Classification of Polymers: Reaction Type
27.4
Classification of Polymers: Chain Growth and Step Growth
27.7
Addition Polymers: A Review and a Preview
27.8
Chain Branching in Free-Radical Polymerization
27.9
Anionic Polymerization: Living Polymers
Textbook Solutions for Organic Chemistry,
Chapter 12.21 Problem 12.32
Question
Write contributing resonance structures to show how the negative charge in the intermediate in the preceding reaction is shared by three ring atoms and the nitrogen of the cyano group. Here is one of the contributing structures to get you started.
Solution
The first step in solving 12.21 problem number 3 trying to solve the problem we have to refer to the textbook question: Write contributing resonance structures to show how the negative charge in the intermediate in the preceding reaction is shared by three ring atoms and the nitrogen of the cyano group. Here is one of the contributing structures to get you started.
From the textbook chapter Related Nucleophilic Aromatic Substitutions you will find a few key concepts needed to solve this.
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full solution
full solution
Title
Organic Chemistry, 9
Author
Francis A Carey Dr., Robert M. Giuliano
ISBN
9780073402741
Write contributing resonance structures to show how the negative charge in the
Chapter 12.21 textbook questions
-
Chapter 12: Problem 12 Organic Chemistry, 9
-
Chapter 12: Problem 12 Organic Chemistry, 9
Offer an explanation for the observation that 4-chloropyridine is more reactive toward nucleophiles than 3-chloropyridine.
Read more -
Chapter 12: Problem 12 Organic Chemistry, 9
Write contributing resonance structures to show how the negative charge in the intermediate in the preceding reaction is shared by three ring atoms and the nitrogen of the cyano group. Here is one of the contributing structures to get you started.
Read more