Draw the structure of (a) 4-(dimethylamino)pyridine (b) 4-ethyl-2-nitroimidazole
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Table of Contents
1
Chemical Bonding And Chemical Structure
1.2
Classical theories of chemical Bonding
1.3
Structures of Covalent Compounds
1.4
Resonance structures
1.6
Electronic structure of the hydrogen atom
1.7
Electronic Structures of more Complex Atoms
1.8
Another look at the covalent bond: Molecular orbitals
1.9
Hybrid orbitals
2
Alkanes
2.2
Unbranched Alkanes
2.3
Conformations of Alkanes
2.4
Constitutional Isomers and Nomenclature
2.5
Cycloalkanes, Skeletal Structures, and Substituent Group Abbreviations
2.6
Physical Properties of Alkanes
2.7
Combustion
2.8
Functional Groups, Compound Classes, and the "R" Notation
3
Acids and Bases. The Curved-Arrow Notation
3.1
Lewis Acid-Base Association Reactions
3.2
Electron-Pair Displacement Reactions
3.3
Using the Curved-Arrow Notation to Derive Resonance Structures
3.4
Bronsted-Lowry Acids and Bases
3.5
Free Energy and Chemical Equilibrium
3.6
The Relationship of Structure to Acidity
4
Inttroduction to Alkanes. Structure and Reactivity
4.1
Structure and Bonding in Alkenes
4.2
Nomenclature of Alkenes
4.3
Unsaturation Number
4.4
Physical Properties of Alkenes
4.5
Relative Stabilities of Alkene Isomers
4.6
Addition Reactions of Alkenes
4.7
Addition of Hydrogen Halides to Alkenes
4.8
Reaction Rates
4.9
Catalysis
5
Addition Reactions of Alkenes
5.1
An Overview of Electrophilic Addition Reactions
5.2
Reactions of Alkenes with Halogens
5.4
Conversion of Alkenes Into Alcohols
5.5
Ozonolysis of Alkenes
5.6
Free-Radical Addtion of Hydrogen Bromide to Alkenes
5.7
Polymers. Free-Radical Polymerization of Alkenes
5.8
Alkenes in the Chemical Industry
6
Principle of Stereochemistry
6.1
Enantiomers, Chirality, and Symmetry
6.10
The Postulation of Tetrahedral Carbon
6.2
Nomenclature of Enantiomers: The R, S System
6.3
Physical Properties of Enantiomers. Optical Activity
6.4
Mixtures of Enantiomers
6.5
Stereochemical Correlation
6.7
Meso Compounds
6.8
Separation of Enantiomers (Enantiomeric Resolution)
6.9
Rapidly Interconverting Stereoisomers
7
Cyclic Compounds. Stereochemistry of Reactions
7.2
Conformations of Cyclohexane
7.3
Monosubstituted Cyclohexanes. Conformational Analysis
7.4
Disubstituted Cyclohexanes
7.5
Cyclopentane, Cyclobutane, and Cyclopropane
7.6
Bicyclic and Polycyclic Compounds
7.7
Reactions Involving Stereoisomers
7.8
Stereochemistry of Chemical Reactions
8.2
Nomenclature of Alkyl Halides, Alcohols, Thiols, Ethers, and Sulfides
8.3
Structures of Alkyl Halides, Alcohols, Thiols, Ethers, and Sulfides
8.5
Homogeneous Noncovalent Intermolecular Attractions: Boiling Points and Melting Points
8.6
Heterogeneous Intermolecular Interactions: Solutions and Solubility
8.7
Applications of Solubility and Solvation Principles
8.8
Strengths of NoncStrenghts of Noncovalent Intermolecular Attractions
9
The Chemistry of Alkyl Halides
9.1
Overview of Nucleophilic Substitution and B-Elimination Reactions
9.10
indUsTrial preparaTion and Use oF alKYl Halides
9.2
Equilibria in Nucleophilic Substitution Reactions
9.3
Reaction Rates
9.4
The SN2 Reaction
9.5
The E2 Reaction
9.6
The SN1 and E1 Reactions
9.7
Summary of Substitution and Elimination Reactions of Alkyl Halides
9.8
Organometallic Compounds. Grignard Reagents and Organolithium Reagents
9.9
Carbenes and Carbenoids
10
The Chemistry of Alcohols and Thiols
10.1
Alcohols and Thiols as Brønsted Acids and Bases
10.10
Octet Expansion and Oxidation of Thiols
10.12
Planning an Organic Synthesis: Restrosynthetic Analysis
10.2
Dehydration of Alcohols
10.3
Reactions of Alcohols with hydrogen Halides
10.4
Alcohol-Derived Leaving Groups
10.5
Conversion of Alcohols into Alkyl Halides: Summary
10.6
Oxidation and Reduction in Organic Chemistry
10.7
Oxidation of Alcohols
10.8
Biological Oxidation of Ethanol
10.9
Chemical and Stereochemical Group Relationships
11
The Chemistry of Ethers, Epoxides, Glycols, and Sulfides
11.1
Basicity of Ethers and Sulfides
11.10
The Three Fundamental Operations of Organic Synthesis
11.11
Synthesis of Enantiomerically Pure Compounds: Asymmetric Epoxidation
11.2
Synthesis of Ethers and Sulfides
11.3
Synthesis of Epoxides
11.4
Cleavage of Ethers
11.5
Nucleophilic Substitution Reactions of Epoxides
11.6
Preparation and Oxidative Cleavage of Glycols
11.7
Oxonium and Sulfonium
11.8
Intramolecular Reactions and the Proximity effect
12
Introduction to Spectroscopy. Infrared Spectroscopy and Mass Spectrometry
12.1
Introduction to Spectroscopy
12.2
Infrared Spectroscopy
12.3
Infrared Absorption and Chemical Structure
12.4
Functional-Group Infrared Absorptions
12.6
Introduction to Mass Spectrometry
13
Nuclear Magnetic Resonance Spectroscopy
13.10
Solving Structure Problems with Spectroscopy
13.2
The Physical Basis of NMR Spectroscopy
13.3
The NMR Spectrum: Chemical Shift and Integral
13.4
The NMR Spectrum: Spin-Spin Splitting
13.5
Complex NMR Spectra
13.6
Using Deuterium Substitution in Proton NMR
13.7
Characteristic Functional-Group NMR Absorptions
13.8
NMR Spectroscopy of Dynamics Systems
13.9
NMR Spectroscopy of other Nuclei, Carbon NMR
14
The Chemistry of Alkynes
14.1
Structure and Bonding in Alkynes
14.2
Nomenclature of Alkynes
14.3
Physical Properties of Alkynes
14.4
Introduction to Addition Reactions of the Triple Bond
14.5
Conversion of Alkynes Into Aldehydes and Ketones
14.6
Reduction of Alkynes
14.7
Acidity of 1-Alkynes
14.8
Organic Synthesis using Alkynes
14.9
Pheromones
15
Dienes, Resonance, and Aromaticity
15.1
Structure and Stability of Dienes
15.2
Ultraviolet–Visible Spectroscopy and Fluorescence
15.3
The Diels–Alder Reaction
15.4
Addition of Hydrogen Halides to Conjugated Dienes
15.5
Diene Polymers
15.6
Resonance
15.7
Introduction to Aromatic Compounds
15.8
Noncovalent Interactions of Aromatic Rings
16
The Chemistry of Benzene and Its Derivatives
16.1
Nomenclature of Benzene Derivatives
16.2
Physical Properties of Benzene Derivatives
16.3
Spectroscopy of Benzene Derivatives
16.4
Electrophilic Aromatic Substitution Reactions of Benzene
16.5
Electrophilic Aromatic Substitution Reactions of Substituted Benzenes
16.6
Hydrogenation of Benzene Derivatives
16.7
Polycyclic Aromatic Hydrocarbons and Cancer
17
Allylic and Benzylic Reactivity
17.1
Reactions Involving Allylic and Benzylic Carbocations
17.2
Reactions Involving Allylic and Benzylic Radicals
17.3
Reactions Involving Allylic and Benzylic Anions
17.4
Allylic and Benzylic SN2 Reactions
17.5
Allylic and Benzylic Oxidation
17.6
biosynthesis of terpenes and steroids
18
THE CHEmisTRy of ARyl HAlidEs, VinyliC HAlidEs, And PHEnols. TRAnsiTion-mETAl CATAlysis
18.1
Lack of Reactivity of Vinylic and Aryl Halides under SN2 Conditions
18.11
Industrial Preparation and use of Phenol
18.2
Elimination Reactions of Vinylic Halides
18.3
Lack of Reactivity of Vinylic and Aryl Halides under SN1 Conditions
18.4
Nucleophilic Aromatic Substitution Reactions of Aryl Halides
18.5
Introduction to Transition-Metal-Catalyzed Reactions
18.6
Examples of Transition-Metal-Catalyzed Reactions
18.7
Acidity of Phenols
18.8
Quinones and Semiquinones
18.9
Electrophilic Aromatic Substitution Reactions of Phenols
19
The Chemistry of Aldehydes and Ketones. Carbonyl-Addition Reactions
19.1
NomeNclature of aldehydes aNd KetoNes
19.11
Reactions of Aldehydes and Ketones with Amines
19.12
Reduction of Carbonyl Groups to Methylene Groups
19.13
The Wittig Alkene Synthesis
19.14
Oxidation of Aldehydes to Carboxylic Acids
19.3
Spectroscopy of Aldehydes and Ketones
19.6
Basicity of Aldehydes and Ketones
19.7
Reversible Addition Reactions of Aldehydes and Ketones
19.8
Reduction of Aldehydes and Ketones to Alcohols
19.9
Reactions of Aldehydes and Ketones with Grignard and Related Reagents
20
The Chemistry of Carboxylic Acids
20.1
Nomenclature of Carboxylic Acids
20.11
Decarboxylation of Carboxylic Acids
20.2
Structure and Physical Properties of Carboxylic Acids
20.3
Spectroscopy of Carboxylic Acids
20.4
Acid–Base Properties of Carboxylic Acids
20.6
Synthesis of Carboxylic Acids
20.8
Conversion of Carboxylic Acids Into Esters
20.9
Conversion of Carboxylic Acids Into Acid Chlorides and Anhydrides
21
The Chemistry of Carboxylic Acid Derivatives
21.1
Nomenclature and Classification of Carboxylic Acid Derivatives
21.11
Synthesis of Carboxylic Acid Derivatives
21.12
Use and Occurrence of Carboxylic Acids and their Derivatives
21.2
Structures of Carboxylic Acid Derivatives
21.3
Physical Properties of Carboxylic Acid Derivatives
21.4
Spectroscopy of Carboxylic Acid Derivatives
21.5
Basicity of Carboxylic Acid Derivatives
21.7
Hydrolysis of Carboxylic Acid Derivatives
21.8
Reactions of Carboxylic Acid Derivatives with Nucleophiles
21.9
Reduction of Carboxylic Acid Derivatives
22
The Chemistry of Enolate Ions, Enols, and a,b-Unsaturated Carbonyl Compounds
22.1
Acidity of Carbonyl Compounds
22.11
Reactions of a,b-Unsaturated Carbonyl Compounds with Organometallic Reagents
22.12
Organic Synthesis with Conjugate-Addition Reactions
22.2
Enolization of Carbonyl Compounds
22.3
a-Halogenation of Carbonyl Compounds
22.4
Aldol Addition and Aldol Condensation
22.5
Aldol Reactions in Biology
22.6
Condensation Reactions Involving ESTER Enolate Ions
22.7
The Claisen Condensation in Biology: Biosynthesis of Fatty Acids
22.8
Alkylation and Aldol Reactions of Ester Enolate Ions
22.9
Conjugate-Addition Reactions
23
The Chemistry of Amines
23.1
Nomenclature of Amines
23.11
Synthesis of Amines
23.12
Use and Occurrence of Amines
23.2
Structure of Amines
23.4
Spectroscopy of Amines
23.5
Basicity and Acidity of Amines
23.6
Quaternary Ammonium and Phosphonium Salts
23.7
Alkylation and Acylation Reactions of Amines
23.8
Hofmann Elimination of Quaternary Ammonium Hydroxides
23.9
Aromatic Substitution Reactions of Aniline Derivatives
24
Carbohydrates
24.10
The Proof of Glucose Stereochemistry
24.11
DisacchariDes anD polysacchariDes
24.2
Fischer Projections
24.3
Structures of the Monosaccharides
24.5
Base-Catalyzed Isomerization of Aldoses and Ketoses
24.6
Glycosides
24.7
Ether and Ester Derivatives of Carbohydrates
24.8
Oxidation and Reduction Reactions of Carbohydrates
24.9
Kiliani–Fischer Synthesis
25
The Chemistry of Thioesters, Phosphate Esters, and Phosphate Anhydrides
25.1
Thioesters
25.2
Phosphoric Acid Derivatives
25.3
Structures of Thioesters and Phosphate Esters
25.4
Proton and Carbon NMR Spectroscopy of Phosphorus-Containing Molecules
25.5
Reactions of Thioesters with Nucleophiles
25.6
Hydrolysis of Phosphate Esters and Anhydrides
25.7
Reactions of Phosphate Anhydrides with other Nucleophiles
25.8
“High-Energy” Compounds
26
The Chemistry of the Aromatic Heterocycles and Nucleic Acids
26.1
Nomenclature and Structure of the Aromatic Heterocycles
26.2
Basicity and Acidity of the Nitrogen Heterocycles
26.3
The Chemistry of Furan, Pyrrole, and Thiophene
26.4
The Chemistry of Pyridine
26.5
Nucleosides, Nucleotides, and Nucleic Acids
Textbook Solutions for Organic Chemistry
Chapter 26.1 Problem 26.5
Question
Each of the following NMR chemical shifts goes with a proton at carbon-2 of either pyridine, pyrrolidine, or pyrrole. Match each chemical shift with the appropriate heterocyclic compound, and explain your answer: d 8.51; d 6.41; and d 2.82.
Solution
The first step in solving 26.1 problem number 5 trying to solve the problem we have to refer to the textbook question: Each of the following NMR chemical shifts goes with a proton at carbon-2 of either pyridine, pyrrolidine, or pyrrole. Match each chemical shift with the appropriate heterocyclic compound, and explain your answer: d 8.51; d 6.41; and d 2.82.
From the textbook chapter Nomenclature and Structure of the Aromatic Heterocycles you will find a few key concepts needed to solve this.
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full solution
Title
Organic Chemistry 6
Author
Marc Loudon, Jim Parise
ISBN
9781936221349
Each of the following NMR chemical shifts goes with a proton at carbon-2 of either
Chapter 26.1 textbook questions
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Chapter 26: Problem 26 Organic Chemistry 6
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Chapter 26: Problem 26 Organic Chemistry 6
Name the following compounds. (a) (b) (c) N CH O (d)
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Chapter 26: Problem 26 Organic Chemistry 6
Draw the important resonance structures for pyrrole
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Chapter 26: Problem 26 Organic Chemistry 6
(a) The dipole moments of pyrrole and pyrrolidine are similar in magnitude but have opposite directions. Explain, indicating the direction of the dipole moment in each compound. (Hint: Use the result in Problem 26.3.) (b) Explain why the dipole moments of furan and pyrrole have opposite directions. (c) Should the dipole moment of 3,4-dichloropyrrole be greater than or less than that of pyrrole? Explain.
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Chapter 26: Problem 26 Organic Chemistry 6
Each of the following NMR chemical shifts goes with a proton at carbon-2 of either pyridine, pyrrolidine, or pyrrole. Match each chemical shift with the appropriate heterocyclic compound, and explain your answer: d 8.51; d 6.41; and d 2.82.
Read more