1 H NMR Spectra Of Four Isomeric Alcohols With Formula C9H12O Are ...

×

• Login to your accountor Register for free
• Notes & Study Guides
• Textbook Answers
• Exam Prep Videos

• Chemistry / Organic Chemistry, 9 / Chapter 13 / Problem 13.40

Table 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 13 Problem 13.40 Chapter (select chapter) 1 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 1.10 1.11 1.12 1.13 1.14 1.15 1.16 2 2.4 2.7 2.8 2.9 2.12 2.13 2.14 2.15 2.16 2.17 2.18 2.19 2.20 2.21 2.22 3 3.1 3.2 3.3 3.5 3.8 3.10 3.11 3.12 3.14 3.15 4 4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.8 4.9 4.11 4.12 4.15 4.16 4.17 5 5.1 5.2 5.3 5.4 5.5 5.6 5.7 5.9 5.10 5.11 5.12 5.13 5.14 5.15 5.16 5.17 5.18 6 6.1 6.2 6.3 6.4 6.5 6.6 6.7 6.8 6.10 6.11 6.12 6.13 6.14 6.15 7 7.2 7.3 7.4 7.5 7.6 7.7 7.8 7.9 7.10 7.11 7.12 7.13 7.14 7.15 8 8.1 8.2 8.3 8.4 8.6 8.7 8.8 8.9 8.10 8.11 8.12 9 9.1 9.2 9.4 9.5 9.6 9.7 9.9 9.10 9.11 9.12 9.14 9.15 10 10.1 10.2 10.3 10.4 10.5 10.6 10.7 10.8 10.9 10.10 10.11 10.12 10.13 11 11.2 11.3 11.5 11.6 11.8 11.9 11.10 11.11 11.12 11.13 11.15 11.16 11.17 11.18 11.19 11.20 11.21 11.22 12 12.2 12.3 12.4 12.5 12.6 12.7 12.8 12.10 12.11 12.12 12.13 12.14 12.15 12.16 12.17 12.18 12.19 12.20 12.21 13 13.3 13.4 13.5 13.6 13.7 13.8 13.11 13.12 13.14 13.15 13.16 13.18 13.20 13.21 13.22 13.23 13.24 13.25 14 14.1 14.3 14.4 14.5 14.7 14.8 14.9 14.10 14.11 14.12 14.13 15 15.2 15.4 15.5 15.7 15.8 15.9 15.10 15.11 15.12 16 16.1 16.2 16.3 16.4 16.5 16.6 16.8 16.9 16.10 16.11 16.12 16.14 16.15 16.16 16.17 17 17.1 17.3 17.4 17.6 17.7 17.8 17.9 17.10 17.11 17.12 17.13 18 18.1 18.4 18.5 18.6 18.7 18.9 18.11 18.12 19 19.1 19.2 19.3 19.4 19.5 19.8 19.9 19.10 19.11 19.12 19.13 19.14 19.15 19.16 19.17 20 20.1 20.2 20.3 20.4 20.5 20.6 20.7 20.8 21 21.1 21.2 21.4 21.7 21.8 21.9 21.10 21.13 21.14 21.15 21.17 21.18 22 22.1 22.3 22.4 22.5 22.6 22.8 22.9 22.11 22.13 23 23.2 23.3 23.4 23.6 23.7 23.8 23.9 23.10 23.11 23.12 23.14 23.15 23.17 23.18 23.20 24 24.2 24.3 24.4 24.5 24.6 24.7 24.9 24.10 24.11 24.12 24.16 25 25.1 25.2 25.3 25.4 25.5 25.6 25.7 25.9 25.10 25.12 25.15 25.16 25.17 25.18 26 26.1 26.2 26.3 26.5 26.7 26.9 26.10 26.12 26.13 27 27.2 27.3 27.4 27.7 27.8 27.9 27.11 27.12 27.13 27.14 Problem 13.31 13.32 13.33 13.34 13.35 13.36 13.37 13.38 13.39 13.40 13.41 13.42 13.43 13.44 13.45 13.46 13.47 13.48 13.49 13.50 13.51 13.52 13.54 13.55 13.56 13.57 13.58

Question

1 H NMR spectra of four isomeric alcohols with formula C9H12O are shown in Figure 13.47. Assign a structure for each alcohol and assign the peaks in each spectrum.

Solution

Step 1 of 6)

The first step in solving 13 problem number 10 trying to solve the problem we have to refer to the textbook question: 1 H NMR spectra of four isomeric alcohols with formula C9H12O are shown in Figure 13.47. Assign a structure for each alcohol and assign the peaks in each spectrum. From the textbook chapter Spectroscopy you will find a few key concepts needed to solve this.

Step 2 of 7)

Visible to paid subscribers only

Step 3 of 7)

Visible to paid subscribers only

Subscribe to view thefull solution Get Full Answer Title Organic Chemistry, 9 Author Francis A Carey Dr., Robert M. Giuliano ISBN 9780073402741 1 H NMR spectra of four isomeric alcohols with formula C9H12O are shown in Figure 13.47

Chapter 13 textbook questions

❮

• Chapter 13: Problem 13 Organic Chemistry, 9

  Each of the following compounds is characterized by a 1 H NMR spectrum that consists of only a single peak having the chemical shift indicated. Identify each compound. (a) C8H18; 0.9 (f) C2H3Cl3; 2.7 (b) C5H10; 1.5 (g) C5H8Cl4; 3.7 (c) C8H8; 5.8 (h) C12H18; 2.2 (d) C4H9Br; 1.8 (i) C3H6Br2; 2.6 (e) C2H4Cl2; 3.7

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Deduce the structure of each of the following compounds on the basis of their 1 H NMR spectra and molecular formulas: (a) C8H10; 1.2 (triplet, 3H) (e) C4H6Cl4; 3.9 (doublet, 4H) 2.6 (quartet, 2H) 4.6 (triplet, 2H) 7.1 (broad singlet, 5H) (f) C4H6Cl2; 2.2 (singlet, 3H) (b) C10H14; 1.3 (singlet, 9H) 4.1 (doublet, 2H) 7.0 to 7.5 (multiplet, 5H) 5.7 (triplet, 1H) (c) C6H14; 0.8 (doublet, 12H) (g) C3H7ClO; 2.0 (quintet, 2H) 1.4 (septet, 2H) 2.8 (singlet, 1H) (d) C6H12; 0.9 (triplet, 3H) 3.7 (triplet, 2H) 1.6 (singlet, 3H) 3.8 (triplet, 2H) 1.7 (singlet, 3H) (h) C14H14; 2.9 (singlet, 4H) 2.0 (quintet, 2H) 7.1 (broad singlet, 10H) 5.1 (triplet, 1H)

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  From among the isomeric compounds of molecular formula C4H9Cl, choose the one having a 1 H NMR spectrum that (a) Contains only a single peak (b) Has several peaks including a doublet at 3.4 (c) Has several peaks including a triplet at 3.5 (d) Has several peaks including two distinct three-proton signals, one of them a triplet at 1.0 and the other a doublet at 1.5

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Identify the C3H5Br isomers on the basis of the following information: (a) Isomer A has the 1 H NMR spectrum shown in Figure 13.45. (b) Isomer B has three peaks in its 13C NMR spectrum: 32.6 (CH2); 118.8 (CH2); and 134.2 (CH). (c) Isomer C has two peaks in its 13C NMR spectrum: 12.0 (CH2) and 16.8 (CH). The peak at lower field is only half as intense as the one at higher field.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Identify each of the C4H10O isomers on the basis of their 13C NMR spectra: (a) 18.9 (CH3) (two carbons) 30.8 (CH) (one carbon) 69.4 (CH2) (one carbon) (b) 10.0 (CH3) 22.7 (CH3) 32.0 (CH2) 69.2 (CH) (c) 31.2 (CH3) (three carbons) 68.9 (C) (one carbon)

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  A compound (C3H7ClO2) exhibited three peaks in its 13C NMR spectrum at 46.8 (CH2), 63.5 (CH2), and 72.0 (CH). Excluding compounds that have Cl and OH on the same carbon, which are unstable, what is the most reasonable structure for this compound?

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Label nonequivalent carbons in the following compounds.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  The 1 H NMR spectrum of fluorene has signals at 3.8 and 7.27.7 in a 1:4 ratio. After heating with NaOCH3 in CH3OD at reflux for 15 minutes the signals at 7.27.7 remained, but the one at 3.8 had disappeared. Suggest an explanation and write a mechanism for this observation.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  The vinyl proton region of the 1 H NMR spectrum of phenyl vinyl sulfoxide is shown in Figure 13.46. Construct a splitting diagram similar to the one in Figure 13.21 and label each of the coupling constants Ja,b, Jb,c, and Ja,c.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  1 H NMR spectra of four isomeric alcohols with formula C9H12O are shown in Figure 13.47. Assign a structure for each alcohol and assign the peaks in each spectrum.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Compounds A and B are isomers of molecular formula C10H14. Identify each one on the basis of the 13C NMR spectra presented in Figure 13.48.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Identify the hydrocarbon that gives the IR spectrum shown in Figure 13.49 and has an M+ peak at m/z 102 in its mass spectrum.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  A compound (C8H10O) has the IR and 1 H NMR spectra presented in Figure 13.50. What is its structure?

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Deduce the structure of a compound having the mass, IR, and 1 H NMR spectra presented in Figure 13.51.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  13C NMR spectra for four isomeric alkyl bromides with the formula C5H11Br are shown in Figure 13.52. Multiplicities obtained from DEPT analysis are shown above each peak. Assign structures to each of the alkyl bromides and assign the peaks in each spectrum.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Figure 13.53 presents IR, 1 H NMR, 13C NMR, and mass spectra for a particular compound. What is it?

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Which would you predict to be more shielded, the inner or outer protons of [24]annulene?

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  19F is the only isotope of fluorine that occurs naturally, and it has a nuclear spin of 1 2 . (a) Into how many peaks will the proton signal in the 1 H NMR spectrum of methyl fluoride be split? (b) Into how many peaks will the fluorine signal in the 19F NMR spectrum of methyl fluoride be split? (c) The chemical shift of the protons in methyl fluoride is 4.3. Given that the geminal 1 H 19F coupling constant is 45 Hz, specify the values at which peaks are observed in the proton spectrum of this compound at 300 MHz.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  31P is the only phosphorus isotope present at natural abundance and has a nuclear spin of 1 2 . The 1 H NMR spectrum of trimethyl phosphite, (CH3O)3P, exhibits a doublet for the methyl protons with a splitting of 12 Hz. (a) Into how many peaks is the 31P signal split? (b) What is the difference in chemical shift (in hertz) between the lowest and highest field peaks of the 31P multiplet?

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  We noted in Section 13.13 that an NMR spectrum is an average spectrum of the conformations populated by a molecule. From the following data, estimate the percentages of axial and equatorial bromine present in bromocyclohexane.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  1 H NMR, 13C NMR, IR, and mass spectra are shown for a compound in Figure 13.54. Propose a structure and explain your answer based on spectral assignments.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  1 H NMR and IR spectra for a compound with the formula C7H7NO3 are shown in Figure 13.55. Assign a structure and explain your reasoning.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Refer to Figure 13.57 and Table 13.5 to assign chemical shifts for the vinylic protons Ha, Hb, and Hc in vinyl acetate. (a) Ha: 4.57 Hb: 4.88 Hc: 7.28 (b) Ha: 4.88 Hb: 4.57 Hc: 7.28 (c) Ha: 7.28 Hb: 4.88 Hc: 4.57 (d) Ha: 7.28 Hb: 4.57 Hc: 4.88

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Which one of the following statements incorrectly describes the expected coupling of the proton at C(1) in the stereoisomeric 4-tert-butylcyclohexanols? 1 OH cis-4-tert-Butylcyclohexanol 1 trans-4-tert-Butylcyclohexanol OH H H 2 6 2 6 In the trans isomer the coupling constant between: (a) the proton at C(1) and the axial protons at C(2) and C(6) is 8 Hz. (b) the proton at C(1) and the equatorial protons at C(2) and C(6) is 2 Hz. In the cis isomer the coupling constant between: (c) the proton at C(1) and the axial protons at C(2) and C(6) is 8 Hz. (d) the proton at C(1) and the equatorial protons at C(2) and C(6) is 2 Hz.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Apiose is one of several naturally occurring carbohydrates characterized by a branched carbon chain and is conveniently isolated as the compound shown (diacetone apiose). Based on the observation that the protons at C(1) and C(2) have a coupling constant of 3.7 Hz, choose the correct statement. O O O H H O O 1 2 Diacetone apiose (a) The C(1) and C(2) protons are eclipsed. (b) The H C(1) C(2) H dihedral angle is in the range 3060. (c) The H C(1) C(2) H dihedral angle is in the range 145165 (d) The C(1) and C(2) protons are anti.

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  The region of the 1 H NMR spectrum showing the signal for H1 of a mixture of two isomers of glucose is shown in Figure 13.59. Which is the major isomer? (a) Isomer A (b) Isomer B

  Read more
• Chapter 13: Problem 13 Organic Chemistry, 9

  Figure 13.60 shows a portion of the 1 H NMR spectrum of 2,4-dibromoacetanilide. Which of the following corresponds to the chemical shift assignments for the ring protons? (a) Ha: 8.27 Hb: 7.68 Hc: 7.43 (b) Ha: 8.27 Hb: 7.43 Hc: 7.68 (c) Ha: 7.43 Hb: 8.27 Hc: 7.68 (d) Ha: 7.68 Hb: 7.43 Hc: 8.27

  Read more

❯ ×

Login

Organize all study tools for free

Or continue with Log in Forgot password? | Register Now ×

Register

Sign up for access to all content on our site!

Or continue with Register

Or login if you already have an account

×

Reset password

If you have an active account we’ll send you an e-mail for password recovery

Reset Password

Or login if you have your password back