Chemistry. Organic. A Mechanistic Approach. Penny Chaloner. CRC Press. J Taylor & Francis Group Boca Raton London New York QJ*"
|
|
- Carol Anthony
- 5 years ago
- Views:
Transcription
1 Organic Chemistry A Mechanistic Approach Penny Chaloner ^ QJ*" CRC Press J Taylor & Francis Group Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Croup, an informa business
2 Contents Preface Acknowledgments Author xvii xix xxi Chapter 1 Review of Atomic and Molecular Structure Introduction Atomic and Molecular Structure Orbitals of the Hydrogen Atom Multielectron Atoms Bonding 8 Review Problems 11 Chapter 2 Alkanes and Friends: Structure, Bonding, Properties, and Nomenclature Introduction Hybridization in Methane, Ammonia, and Water Drawing Molecules Introduction to Alkanes Formal Nomenclature of Alkanes Structural Isomers and Formal Nomenclature Haloalkanes Cycloalkanes Stability, Strain, and Properties of Alkanes and Cycloalkanes 31 Review Problems 33 Chapter 3 Alkenes, Alkynes, and Aromatic Compounds Alkenes Bonding in Alkenes Nomenclature of Alkenes Geometric Isomerism in Alkenes Stability of Alkenes and the Effect of Conjugation Aromatic Hydrocarbons Bonding in Aromatic Compounds Nomenclature of Benzene Derivatives Alkynes: Hydrocarbons Containing Triple Bonds Resonance 66 Review Problems 71 Chapter 4 Heteroatom-Containing Functional Groups Compounds Containing sp3 Nitrogen Atoms Molecules Containing sp2 Nitrogen Atoms Molecules with sp-hybridized Nitrogen Compounds Containing sp3 Oxygen Alcohols Ethers Crown Ethers, lonophores, and the Solvation of Metal Ions 91 vii
3 viii Contents 4.5 Compounds Containing sp2 Oxygen Aldehydes Ketones Carboxylic Acids Carboxylate Esters Amides Acyl Halides and Anhydrides Priorities in Nomenclature Structure and Bonding in Some Highly Reactive Species Carbocations Carbanions Carbon-Centered Radicals More Resonance 112 Review Problems 113 More Challenging Problems 118 Chapter 5 Purification and Identification of Organic Compounds Introduction Purification of Organic Compounds Crystallization Distillation and Sublimation Chromatography Mass Spectrometry UWVisible Spectroscopy Infrared Spectroscopy Introduction and Theory Regions of the Infrared Spectrum 154 Review Problems 169 More Challenging Problems 171 Chapter 6 Identification of Organic Compounds 2: Nuclear Magnetic Resonance Spectroscopy Introduction Chemical Shifts Spin-Spin Coupling Simple Aliphatic Systems Spin-Spin Coupling Involving Protons Attached to sp2 Carbon Atoms Spin-Spin Decoupling Protons Attached to Oxygen and Nitrogen ,3C NMR Spectroscopy 209 Review Problems 215 More Challenging Problems 219 Chapter 7 Stereochemistry Introduction Conformations of Alkanes Cycloalkanes Cyclopropane Cyclobutane Cyclopentane Six-Membered Rings Medium and Large Rings Ring Synthesis 233
4 Contents ix 7.4 Chirality Absolute Configuration Molecules with More than One Chiral Center Chiral Molecules with Noncarbon Chiral Centers Other Chiral Compounds Fischer Projections 255 Review Problems 259 More Challenging Problems 262 Chapter 8 Introduction to Mechanism Introduction Studying Organic Reaction Mechanisms Thermodynamics Kinetics Study of Products Isotopic Labeling and Kinetic Isotope Effects Study of Intermediates Classification of Reactions Acids and Bases Orbital Effects Electronegativity Inductive Effects Derealization Solvation Hydrogen Bonding Steric Effects Aromaticity Tautomers: A Slight Digression Writing Mechanisms Using Curly Arrows 296 Review Problems 304 More Challenging Problems 311 Chapter 9 Nucleophilic Substitution at Saturated Carbon Introduction Mechanistic Types Stereochemical Implications Effect of Nucleophile Effect of the Leaving Group Effect of Substrate Structure SN1 Reactions SN2 Reactions Effect of Solvents Competing Reactions Competition between SN1 and SN2 Processes Applications and Scope of the Reaction Halide Ions as Nucleophiles Oxygen and Sulfur as Nucleophiles Nitrogen Nucleophiles Carbon Nucleophiles Neighboring Group Participation and Intramolecular Reactions 365 Review Problems 369 More Challenging Problems 376
5 x Contents Chapter 10 Elimination Reactions Introduction Mechanisms El Elimination, Unimolecular E2 Elimination, Bimolecular E1cB Elimination, Unimolecular, Conjugate Base Stereochemistry E1 Eliminations E2 Eliminations E1cB Eliminations Regiochemistry Effect of Substrate Substitution versus Elimination Carbocation Rearrangements Examples and Applications E1 Reactions E2 Reactions ElcB Reactions Mixed or Variable Mechanisms Elimination to Give Alkynes Other Elimination Reactions 406 Review Problems 410 More Challenging Proolems 416 Chapter 11 Addition Reactions Introduction Electrophilic Reactions Reaction Mechanism Scope of the Reaction Electrophilic Addition to Conjugated Dienes Terpenes: Biology Oligomerizes Dienes Electrophilic Addition to Alkynes Radical Addition Reactions Multicenter Processes Epoxidation Using Peracids Carbene Addition Hydroboration Dihydroxylation of Alkenes Ozonolysis Cycloadditions, Diels-Alder Reactions Hydrogenation 478 Review Problems 484 More Challenging Problems 493 Chapter 12 Electrophilic Aromatic Substitution Introduction Electrophiles Protons Carbocations Halogens Nitration Sulfonation Orientation Effects Inductive Donors Resonance Donors 514
6 Contents xi Resonance Acceptors Halogens Two or More Groups in Conflict Partial Rate Factors Reactions of Polycyclic Aromatic Compounds Heterocyclic Aromatic Compounds Pyridine and Related Compounds Analogues of the Cyclopentadienyl Anion 532 Review Problems 536 More Challenging Problems 544 Chapter 13 Nucleophilic Aromatic Substitution and Synthesis of Aromatic Compounds Introduction Unimolecular Nucleophilic Substitution of Aromatic Compounds: The Reactions of Diazonium Salts with Simple Nucleophiles Azo Coupling Reactions Nucleophilic Substitution of Aryl Halides, SN2Ar Substitution of Haloheterocycles Substitution via Benzyne and Related Intermediates Reactions in Side Chains of Aromatic Compounds Reactions of Alkylbenzenes Reduction of Nitro Groups Reduction of Aryl Ketones Reduction of Benzene Rings Carbon-Aryl Bond Formation Friedel-Crafts Alkylation and Acylation Haloalkylation Reactions Reactions of Grignard Reagents Nucleophilic Substitution by Cyanide Aromatic Synthesis 582 Review Problems 590 More Challenging Problems 599 Chapter 14 Addition to Carbon-Heteroatom Double Bonds Introduction and Review Mechanism of Addition Reactions Reversible Addition Reactions Cyanohydrin Formation Hydrates, Hemiacetals, and Acetals Acetals and Thioacetals Imines, Enamines, Oximes, and Hydrazones Irreversible Addition Reactions Replacement of Carbonyl Oxygen by Hydrogen Addition of Hydride: Reduction to Alcohols or Amines Addition of Carbon Nucleophiles Wittig Reactions 648 Review Problems 652 More Challenging Problems 660 Chapter 15 Substitution of Carbonyl Compounds: Carboxylic Acids and Their Derivatives Introduction: Review of Nomenclature Substitution Reaction Effect of Substrate Effect of Leaving Group 672
7 xii Contents 15.3 Oxygen Nucleophiles Nitrogen Nucleophiles Synthesis of Acid Chlorides Hydride as Nucleophile Carbon Nucleophiles Grignard Reagents Organolithium Compounds Organocadmium Compounds Organozinc Compounds: The Reformatskii Reaction Organocopper Reagents 701 Review Problems 703 More Challenging Problems 712 Chapter 16 Lipids and Carbohydrates Introduction Lipids Surfactants Fatty Acids and Triglycerides Prostaglandins Waxes Steroids Carbohydrates Introduction Triose Sugars Tetrose Sugars Pentose Sugars Hexose Sugars Cyclic Forms of Sugars Substitution of the OH Groups of Sugars Oxidation Reactions Reduction Chain Lengthening and Shortening Reactions Disaccharides Polysaccharides 768 Review Problems 770 More Challenging Problems 775 Chapter 17 Substitution a and p to Carbonyl Groups Introduction Formation of Enolsand Enolates Isomerizations Involving Enolsand Enolates Reactions of Enols and Enolates with Electrophiles Reaction with Halogens Aldol Reaction Claisen Ester Condensation Alkylation of p-dicarbonyl Compounds Alkylation of Simple Ketones Reactions of Enamines Revisiting the Reformatskii Reaction Two Useful Reactions of Nonenolizable Carbonyl Compounds Reactions at the p-position of a,p-unsaturated Carbonyl Compounds and Other Electron-Poor Alkenes Reactions of Enones with Simple Nucleophiles Conjugate Addition to Other Electron-Poor Alkenes Epoxidation of Electron-Poor Alkenes Organometallic Nucleophiles 825
8 Contents xiii Addition of Enolate Anions to Enones Robinson Annulation: A Look Ahead to Synthesis 830 Review Problems 833 More Challenging Problems 842 Chapter 18 Rearrangement Reactions Introduction Migration to Electron-Deficient Carbon Carbocation Rearrangements Pinacol and Semipinacol Rearrangements Dienone-Phenol Rearrangements Migration to Electron-Deficient Nitrogen Beckmann Rearrangement Hofmann Degradation: A Chain-Shortening Reaction Migration to Electron-Deficient Oxygen: The Baeyer-Villiger Oxidation Anionic Rearrangements Neutral Rearrangements Electrocyclic Reactions Sigmatropic Rearrangements 875 Review Problems 884 More Challenging Problems 893 Chapter 19 Synthesis 1: One-Group Disconnections Introduction Simple Disconnections and the Retrosynthetic Approach One-Group Disconnections Disconnection of Alcohols Disconnections of Alkenes FGIs and Disconnections Leading to Aldehydes and Ketones FGIs and Disconnections to Prepare Carboxylic Acids 929 Review Problems 932 More Challenging Problems 937 Chapter 20 Synthesis 2: Two-Group Disconnections and Protecting Groups Introduction to Two-Group Disconnections ,2-Difunctionalized Compounds Addition to Double Bonds Acyl Anion Equivalents Radical Coupling Reactions Other Reactions ,3-Difunctionalized Compounds p-hydroxyketones: The Aldol Condensation oc,p-unsaturated Aldehydes and Ketones ,3-Diketones p-ketoesters Two Important Synthons for Ester Enolates ,4-Difunctionalized Compounds ,5-Difunctionalized Compounds Robinson Annulation ,6-Difunctionalized Compounds Pericyclic Disconnections Protecting Groups Protection of Aldehydes and Ketones Protection of Alcohols 980
9 xiv Contents Protection of 1,2- and 1,3-Diols Protection of Carboxylic Acids Protection of Amines 985 Further Reading 986 Review Problems 986 More Challenging Problems 995 Chapter 21 Polymeric Materials Introduction Polymer Structures Preparation of Addition or Chain-Growth Polymers Radical Polymerization Cationic Polymerization Anionic Polymerization Metal-Mediated Polymerizations Scope of Polymerization of Substituted Alkenes Polymerization of Dienes Ring-Opening Polymerization Preparation of Step-Reaction Polymers Polyesters and Polycarbonates Polyamides Other Polymers Unusual Biopolymers It's a Sticky Business Chewing It Over Pretty as a Picture 1036 Review Problems 1038 More Challenging Problems 1043 Chapter 22 Amines, Alkaloids, Amino Acids, Peptides, and Nucleic Acids Synthesis of Amines Syntheses Involving Nucleophilic Substitution Syntheses from Amides Reduction and Addition at Carbon-Nitrogen Double Bonds Reduction of Nitro Compounds Alkaloids Amino Acids Synthesis of Amino Acids Resolution of Amino Acids Reactions of Amino Acids Peptides Structures of Peptides and Proteins Synthesis Analysis of Peptides Nucleic Acids 1083 Review Problems 1090 More Challenging Problems 1097 Chapter 23 Catalysis of Organic Reactions Introduction Catalysis by Acids and Bases Lewis Acid Catalysis Reactions of Carbonyl Compounds Catalysis of Diels-Alder Reactions.'. 1110
10 Contents xv 23.4 Phase-Transfer Catalysis Reactions Catalyzed by Metal Surfaces Reactions Catalyzed by Transition Metal Complexes Wacker Oxidation and Related Reactions Homogeneous Hydrogenation Coupling Reactions Organocatalysis Enzyme Catalysis 1134 Review Problems 1139 More Challenging Problems 1143 Chapter 24 Organic Chemistry in Industry Introduction Process Chemistry versus Research Chemistry Pharmaceutical Industry Introduction Drug Discovery Drug Development: Preclinical Testing Drug Development: Clinical Testing Personalized Medicine The Future: Problems and Opportunities Agrochemicals Herbicides Fungicides Insecticides Dyes and Colorants Textile Dyes Food Dyes 1170 Review Problems 1173 Further Reading 1174 Chapter 25 Organic Chemistry and the Environment Introduction Pesticides Endocrine Disruptors Chlorofluorocarbons and Their Replacements Polycyclic Aromatic Hydrocarbons Plastics: Recycle, Degrade, or Burn? Is "Green Chemistry" the Future? 1192 Review Problems 1196 Further Reading 1197 Chapter 26 Organic Chemistry in Forensic Science Introduction Drugs of Abuse Categories of Drugs of Abuse Presumptive Tests for Drugs of Abuse Instrumental Methods Designer Drugs Poisons and Poisoning Testing for Blood Dyes, Inks, and Paper 1224
11 xvi Contents 26.6 Trace Evidence Visualization of Fingerprints 1232 Review Problems 1234 Appendix A: Glossary of Abbreviations and Acronyms 1239 Appendix B: Some Common/Trivial Names You Need to Know 1247 Index 1249
Keynotes in Organic Chemistry
Keynotes in Organic Chemistry Second Edition ANDREW F. PARSONS Department of Chemistry, University of York, UK Wiley Contents Preface xi 1 Structure and bonding 1 1.1 Ionic versus covalent bonds 1 1.2
More informationORGANIC CHEMISTRY. Fifth Edition. Stanley H. Pine
ORGANIC CHEMISTRY Fifth Edition Stanley H. Pine Professor of Chemistry California State University, Los Angeles McGraw-Hill, Inc. New York St. Louis San Francisco Auckland Bogota Caracas Lisbon London
More informationKOT 222 Organic Chemistry II
KOT 222 Organic Chemistry II Course Objectives: 1) To introduce the chemistry of alcohols and ethers. 2) To study the chemistry of functional groups. 3) To learn the chemistry of aromatic compounds and
More informationExam 1 (Monday, July 6, 2015)
Chem 231 Summer 2015 Assigned Homework Problems Last updated: Friday, July 24, 2015 Problems Assigned from Essential Organic Chemistry, 2 nd Edition, Paula Yurkanis Bruice, Prentice Hall, New York, NY,
More informationModule9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area
1 CHEMISTRY 263 HOME WORK Lecture Topics: Module7. Hydrogenation of Alkenes The Function of the Catalyst - Syn and anti- addition Hydrogenation of Alkynes - Syn- addition of hydrogen: Synthesis of cis-alkenes
More informationORGANIC CHEMISTRY. Wiley STUDY GUIDE AND SOLUTIONS MANUAL TO ACCOMPANY ROBERT G. JOHNSON JON ANTILLA ELEVENTH EDITION. University of South Florida
STUDY GUIDE AND SOLUTIONS MANUAL TO ACCOMPANY ORGANIC CHEMISTRY ELEVENTH EDITION T. W. GRAHAM SOLOMONS University of South Florida CRAIG B. FRYHLE Pacific Lutheran University SCOTT A. SNYDER Columbia University
More informationCape Cod Community College
Cape Cod Community College Departmental Syllabus Prepared by the Department of Natural Sciences & Applied Technology Date of Departmental Approval: February 3, 2014 Date Approved by Curriculum and Programs:
More informationCHEMISTRY 263 HOME WORK
Lecture Topics: CHEMISTRY 263 HOME WORK Module7: Hydrogenation of Alkenes Hydrogenation - syn and anti- addition - hydrogenation of alkynes - synthesis of cis-alkenes -synthesis of trans-alkenes Text sections:
More informationKJM 3200 Required Reading (Pensum), Fall 2016
KJM 3200 Required Reading (Pensum), Fall 2016 John McMurry: Organic Chemistry 8 nd ed. or Paula Y. Bruice, Organic Chemistry 7 nd ed. as specified below, as specified below. Lise-Lotte Gundersen KJM 3200.
More informationOrganic Chemistry Curriculum Content Outline
Organic Chemistry 2014-15 Curriculum Content Outline CHEM 0203: Organic Structure and Reactivity 1. Structure & Bonding (Brief Review from General Chemistry) a. Ionic & Covalent Bonding b. Lewis Structures
More informationDetailed Course Content
Detailed Course Content Chapter 1: Carbon Compounds and Chemical Bonds The Structural Theory of Organic Chemistry 4 Chemical Bonds: The Octet Rule 6 Lewis Structures 8 Formal Charge 11 Resonance 14 Quantum
More informationJEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II. 5 Credit Hours. Prepared by: Richard A. Pierce
JEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II 5 Credit Hours Prepared by: Richard A. Pierce Revised Date: January 2008 by Ryan H. Groeneman Arts & Science Education Dr. Mindy Selsor, Dean
More informationSeptember [KV 804] Sub. Code: 3804
September 2009 [KV 804] Sub. Code: 3804 (Regulations 2008-2009) (Candidates admitted from 2008-2009 onwards) Paper IV PHARMACEUTICAL ORGANIC CHEMISTRY Time : Three hours Maximum : 70 marks Answer All questions
More informationCOURSE UNIT DESCRIPTION. Dept. Organic Chemistry, Vilnius University. Type of the course unit
Course unit title Organic Chemistry II Lecturer(s) Rimantas Vaitkus COURSE UNIT DESCRIPTION Department Dept. Organic Chemistry, Vilnius University Cycle First Type of the course unit Mode of delivery Period
More informationAn International Thomson Publishing Company
Organic Chemistry Joseph M. Hornback University of Denver 5t Brooks/Cole Publishing Company I(T)P An International Thomson Publishing Company Pacific Grove 'Albany Belmont Bonn Boston Cincinnati Detroit
More informationAdvanced Organic FOURTH. Part A: Structure and Mechanisms
Advanced Organic FOURTH Chemistry EDITION Part A: Structure and Mechanisms Advanced Organic Chemistry PART A: Structure and Mechanisms PART B: Reactions and Synthesis Advanced Organic Chemistry FOURTH
More informationEASTERN ARIZONA COLLEGE General Organic Chemistry I
EASTERN ARIZONA COLLEGE General Organic Chemistry I Course Design 2015-2016 Course Information Division Science Course Number CHM 235 (SUN# CHM 2235) Title General Organic Chemistry I Credits 4 Developed
More informationCHEM2077 HONORS ORGANIC CHEMISTRY SYLLABUS
CHEM2077 HONORS ORGANIC CHEMISTRY SYLLABUS 1. STRUCTURE AND BONDING a] Atomic structure and bonding b] Hybridization and MO Theory c] Drawing chemical structures 2. POLAR COVALENT BONDS: ACIDS AND BASES
More informationCHEM 261 HOME WORK Lecture Topics: MODULE 1: The Basics: Bonding and Molecular Structure Text Sections (N0 1.9, 9-11) Homework: Chapter 1:
CHEM 261 HOME WORK Lecture Topics: MODULE 1: The Basics: Bonding and Molecular Structure Atomic Structure - Valence Electrons Chemical Bonds: The Octet Rule - Ionic bond - Covalent bond How to write Lewis
More informationChapter 18: Ketones and Aldehydes. I. Introduction
1 Chapter 18: Ketones and Aldehydes I. Introduction We have already encountered numerous examples of this functional group (ketones, aldehydes, carboxylic acids, acid chlorides, etc). The three-dimensional
More informationCOURSE UNIT DESCRIPTION. Type of the course unit. Mode of delivery Period of delivery Language of instruction Face to face Autumn English
Course unit title Organic Chemistry I Lecturer(s) Dr. Rimantas Vaitkus COURSE UNIT DESCRIPTION Department Dept. Organic Chemistry, Vilnius University Cycle First Type of the course unit Mode of delivery
More informationMontgomery County Community College CHE 261 Organic Chemistry I
Montgomery County Community College CHE 261 Organic Chemistry I 4-3-3 COURSE DESCRIPTION: This course covers the nomenclature, structure, properties and reactions of many important classes of organic compounds.
More informationAbout the GRE Chemistry Subject Test p. 1 About the GRE Chemistry Subject Test GRE Chemistry Topics Test Dates Testing Fee Test Format Testing Time
About the GRE Chemistry Subject Test p. 1 About the GRE Chemistry Subject Test GRE Chemistry Topics Test Dates Testing Fee Test Format Testing Time Scoring To Guess or Not to Guess On the Day of the Test
More informationOrganic Chemistry 112 A B C - Syllabus Addendum for Prospective Teachers
Chapter Organic Chemistry 112 A B C - Syllabus Addendum for Prospective Teachers Ch 1-Structure and bonding Ch 2-Polar covalent bonds: Acids and bases McMurry, J. (2004) Organic Chemistry 6 th Edition
More informationCHM 292 Final Exam Answer Key
CHM 292 Final Exam Answer Key 1. Predict the product(s) of the following reactions (5 points each; 35 points total). May 7, 2013 Acid catalyzed elimination to form the most highly substituted alkene possible
More informationORGANIC - BROWN 8E CH ALDEHYDES AND KETONES.
!! www.clutchprep.com CONCEPT: ALDEHYDE NOMENCLATURE Replace the suffix of the alkane -e with the suffix On the parent chain, the carbonyl is always terminal, and receive a location As substituents, they
More informationSpring Term 2012 Dr. Williams (309 Zurn, ex 2386)
Chemistry 242 Organic Chemistry II Spring Term 2012 Dr. Williams (309 Zurn, ex 2386) Web Page: http://math.mercyhurst.edu/~jwilliams/ jwilliams@mercyhurst.edu (or just visit Department web site and look
More informationCOURSE OBJECTIVES / OUTCOMES / COMPETENCIES.
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following: See Test1-4 Objectives/Competencies as listed in the syllabus and on the main course
More informationCarbonyl Compounds. Introduction
Carbonyl Compounds Introduction 1 Introduction Two broad classes of compounds contain the carbonyl group: [1] Compounds that have only carbon and hydrogen atoms bonded to the carbonyl [2] Compounds that
More informationUnit title: Organic Chemistry
Unit title: Organic Chemistry Unit code: R/601/0352 QCF level: 4 Credit value: 15 Aim This unit develops the principles and practical techniques of organic chemistry. Rationalisation of structure and bonding
More informationChapter 16. Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group. Physical Properties of Aldehydes and Ketones. Synthesis of Aldehydes
Nomenclature of Aldehydes and Ketones Chapter 16 Aldehydes and Ketones I. Aldehydes replace the -e of the parent alkane with -al The functional group needs no number Nucleophilic Addition to the Carbonyl
More informationJEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II. 5 Credit Hours. Prepared by: Richard A. Pierce. Revised by: Sean Birke October, 2013
JEFFERSON COLLEGE COURSE SYLLABUS CHM201 ORGANIC CHEMISTRY II 5 Credit Hours Prepared by: Richard A. Pierce Revised by: Sean Birke October, 2013 Ms. Linda Abernathy, Math, Science & Business Division Chair
More informationNuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320 I. Isolated, cumulated, and conjugated dienes A diene is any compound with two or C=C's is a diene. Compounds containing more than two
More informationChapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group
Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al
More informationGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C 67/47; telomerisation C08F)
CPC - C07B - 2017.08 C07B GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C 67/47; telomerisation C08F) General methods for the preparation
More informationOrganic Chemistry I and II challenge exam
Organic Chemistry I and II challenge exam Dear student: Organic Chemistry I and II at LCSC covers the standard one year organic curriculum and students take the two-semester ACS exam as their spring final.
More informationChapter 9 Aldehydes and Ketones Excluded Sections:
Chapter 9 Aldehydes and Ketones Excluded Sections: 9.14-9.19 Aldehydes and ketones are found in many fragrant odors of many fruits, fine perfumes, hormones etc. some examples are listed below. Aldehydes
More informationChapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group
Chapter 16 Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group Nomenclature of Aldehydes and Ketones Aldehydes are named by replacing the -e of the corresponding parent alkane with -al
More informationAldehydes and Ketones: Nucleophilic Addition Reactions
Aldehydes and Ketones: Nucleophilic Addition Reactions Why this Chapter? Much of organic chemistry involves the chemistry of carbonyl compounds Aldehydes/ketones are intermediates in synthesis of pharmaceutical
More informationCHAPTER 19: CARBONYL COMPOUNDS III
CHAPTER 19: CARBONYL COMPOUNDS III A hydrogen bonded to a carbon adjacent to a carbonyl carbon is sufficiently acidic to be removed by a strong base. The carbon adjacent to a carbonyl carbon is called
More informationBachelor s Degree in Chemistry. Subject Guide. 1. Information about the subject. 2. Context. 1. Course Identifying Details: ORGANIC CHEMISTRY I
Bachelor s Degree in Chemistry Subject Guide 1. Information about the subject SUBJECT Organic Chemistry I CODE GQUIMI01-2-007 EDUCATIONAL OFFER Bachelor s Degree in Chemistry CENTER Facultad de Química
More informationFARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY. CONTACT HOURS: Lecture: 3 Laboratory: 4
FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY COURSE OUTLINE: COURSE TITLE: Prepared by: Dr. M. DeCastro September 2011 Organic Chemistry II COURSE NUMBER: CHM 271 CREDITS: 5 CONTACT HOURS: Lecture:
More informationA. Loupy, B.Tchoubar. Salt Effects in Organic and Organometallic Chemistry
A. Loupy, B.Tchoubar Salt Effects in Organic and Organometallic Chemistry 1 Introduction - Classification of Specific Salt Effects 1 1.1 Specific Salt Effects Involving the Salt's Lewis Acid or Base Character
More informationAROMATIC & HETEROCYCLIC CHEMISTRY
- 1 - AROMATIC & HETEROCYCLIC CHEMISTRY Aromatic Chemistry Aromaticity This confers an energetic stability over the equivalent double bond system. This can be explained from an MO point of view. The Huckel
More informationIntroduction. A1.1 (a) Shell number and number of subshells 1. A1.1 (b) Orbitals 2. A1.1 (c ) Orbital shapes (s, p & d) 2
Preface Table of Contents Introduction i A1.1 (a) Shell number and number of subshells 1 A1.1 (b) Orbitals 2 A1.1 (c ) Orbital shapes (s, p & d) 2 A1.1 (d) Relative energies of s,p,d,f sub-shells 4 A 1.1
More informationCOWLEY COLLEGE & Area Vocational Technical School
COWLEY COLLEGE & Area Vocational Technical School COURSE PROCEDURE FOR ORGANIC CHEMISTRY II CHM 4251 5 Credit Hours Student Level: This course is open to students on the college level in the sophomore
More informationORGANIC CHEMISTRY FUNDAMENTALS OF T. W. GRAHAM SOLOMONS. University of South Florida
FIFTH EDITION FUNDAMENTALS OF ORGANIC CHEMISTRY T. W. GRAHAM SOLOMONS University of South Florida JOHN WlLEY & SONS, INC. New York Chichester Brisbane Toronto Singapore NTENTS CHAPTER 1 CARBON COMPOUNDS
More informationORGANIC CHEMISTRY G. MARC LOUDON HOFI. The Benjamin/Cummings Publishing Company, Inc. THIRD EDITION PURDUE UNIVERSITY
:, Juli«ORGANIC CHEMISTRY THIRD EDITION G. MARC LOUDON PURDUE UNIVERSITY HOFI The Benjamin/Cummings Publishing Company, Inc. A Division ofaddison-wesley Publishing Company Redwood City, California Menlo
More informationALCOHOLS AND PHENOLS
ALCOHOLS AND PHENOLS ALCOHOLS AND PHENOLS Alcohols contain an OH group connected to a a saturated C (sp3) They are important solvents and synthesis intermediates Phenols contain an OH group connected to
More informationChapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions
Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic
More informationAmines Reading Study Problems Key Concepts and Skills Lecture Topics: Amines: structure and nomenclature
Amines Reading: Wade chapter 19, sections 19-1-19-19 Study Problems: 19-37, 19-39, 19-40, 19-41, 19-44, 19-46, 19-47, 19-48, 19-51, 19-54 Key Concepts and Skills: Explain how the basicity of amines varies
More informationChapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions
Chapter 19. Aldehydes and Ketones: Nucleophilic Addition Reactions شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic
More informationDEPARTMENT: Chemistry
CODE CHEM 204 TITLE: Organic Chemistry II INSTITUTE: STEM DEPARTMENT: Chemistry COURSE DESCRIPTION: A continuation of CHEM-203, students will extend their studies into topics including aromatic hydrocarbons,
More informationThe Basics of General, Organic, and Biological Chemistry
The Basics of General, Organic, and Biological Chemistry By Ball, Hill and Scott Download PDF at https://open.umn.edu/opentextbooks/bookdetail.aspx?bookid=40 Page 5 Chapter 1 Chemistry, Matter, and Measurement
More informationp Bonds as Electrophiles
Chapter 7 p Bonds as Electrophiles REACTIONS OF CARBONYLS AND RELATED FUNCTIONAL GROUPS Copyright 2018 by Nelson Education Limited 1 7.2.1 Orbital structure of the carbonyl group Because oxygen is more
More informationAryl Halides. Structure
Aryl Halides Structure Aryl halides are compounds containing halogen attached directly to an aromatic ring. They have the general formula ArX, where Ar is phenyl, substituted phenyl. X= F,Cl,Br,I An aryl
More informationCourse Syllabus. Department: Science & Technology. Date: April I. Course Prefix and Number: CHM 212. Course Name: Organic Chemistry II
Department: Science & Technology Date: April 2012 I. Course Prefix and Number: CHM 212 Course Name: Organic Chemistry II Course Syllabus Credit Hours and Contact Hours: 5 credit hours and 7 (3:3:1) contact
More informationAdvanced Organic Chemistry
Reinhard Bruckner Advanced Organic Chemistry Reaction Mechanisms An Imprint of Elsevier San Diego San Francisco New York Boston London Sydney Tokyo -- Foreword Preface to the English Edition Preface to
More informationCOURSE OUTLINE Last Revised and Approved: 12/10/2010 CHEM ORGANIC CHEMISTRY I Units Total Total Hrs Lab
CHEM 210 - ORGANIC CHEMISTRY I Units Lecture Total Hrs Lecture 3.00 Units Lab 2.00 Units Total 5.00 49.50 Total Hrs Lab 99.00 Total Course Hrs 148.50 COURSE DESCRIPTION This course is the first semester
More informationHyperlearning MCAT Instructor Qualifying Exam Organic Chemistry
Hyperlearning MCAT Instructor Qualifying Exam Organic Chemistry 30 Questions (5 pages); Time limit = 45 minutes Use of books or notes is not permitted. 1. When analyzed with a polarimeter, which of the
More informationOrganic Chemistry I Lesson Objectives, Lesson Problems, Course Outline Spring 2008
Organic Chemistry I Lesson Objectives, Lesson Problems, Course Outline Spring 2008 Lesson Date Assignment Lesson Objective Description Lesson Problems 4 14-Jan Chapter 1 Quiz Describe how bond polarity
More informationCHEM*2700 ORGANIC CHEMISTRY I (Spring/Summer Semester 2009) Information Sheet and Course Outline
CHEM*2700 ORGANIC CHEMISTRY I (Spring/Summer Semester 2009) Information Sheet and Course Outline Instructor: Professor William Tam Office: MacN 332 Phone: 824-4120 (Ext.52268) E-mail: wtam@uoguelph.ca
More informationLevel I Course Units Offered by The Department of Chemistry For
Level I Course Units Offered by The Department of Chemistry For General Degree (3 year) [Bachelor of Science SLQF5] General Degree (4 year-molecular Biology & Biotechnology) [Bachelor of Science (Molecular
More informationAldehydes and Ketones : Aldol Reactions
Aldehydes and Ketones : Aldol Reactions The Acidity of the a Hydrogens of Carbonyl Compounds: Enolate Anions Hydrogens on carbons a to carbonyls are unusually acidic The resulting anion is stabilized by
More informationCourse Outline. TERM EFFECTIVE: Fall 2016 CURRICULUM APPROVAL DATE: 03/14/2016
5055 Santa Teresa Blvd Gilroy, CA 95023 Course Outline COURSE: CHEM 12A DIVISION: 10 ALSO LISTED AS: TERM EFFECTIVE: Fall 2016 CURRICULUM APPROVAL DATE: 03/14/2016 SHORT TITLE: ORGANIC CHEMISTRY LONG TITLE:
More informationDr. Mohamed El-Newehy
By Dr. Mohamed El-Newehy Chemistry Department, College of Science, King Saud University http://fac.ksu.edu.sa/melnewehy Aldehydes and Ketones 1 Structure of Aldehydes and Ketones - Aldehydes and ketones
More informationCOURSE OBJECTIVES / OUTCOMES / COMPETENCIES.
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following: See Test1-4 Objectives/Competencies as listed in the syllabus and on the main course
More informationWorksheet Chapter 10: Organic chemistry glossary
Worksheet 10.1 Chapter 10: Organic chemistry glossary Addition elimination reaction A reaction in which two molecules combine with the release of a small molecule, often water. This type of reaction is
More informationORGANIC - CLUTCH CH ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION
!! www.clutchprep.com CONCEPT: ALDEHYDE NOMENCLATURE Replace the suffix of the alkane -e with the suffix On the parent chain, the carbonyl is always terminal, and receive a location As substituents, they
More informationBenzene and Aromatic Compounds. Chapter 15 Organic Chemistry, 8 th Edition John McMurry
Benzene and Aromatic Compounds Chapter 15 Organic Chemistry, 8 th Edition John McMurry 1 Background Benzene (C 6 H 6 ) is the simplest aromatic hydrocarbon (or arene). Four degrees of unsaturation. It
More information1. Radical Substitution on Alkanes. 2. Radical Substitution with Alkenes. 3. Electrophilic Addition
1. Radical Substitution on Alkanes Only Cl and Br are useful at the laboratory level. Alkane reactivity: tertiary > secondary > primary > methyl Numbers below products give their relative yield. Relative
More informationCHEM 251 (4 credits): Description
CHEM 251 (4 credits): Intermediate Reactions of Nucleophiles and Electrophiles (Reactivity 2) Description: An understanding of chemical reactivity, initiated in Reactivity 1, is further developed based
More informationChapter 25 Organic and Biological Chemistry
Chapter 25 Organic and Biological Chemistry Organic Chemistry The chemistry of carbon compounds. Carbon has the ability to form long chains. Without this property, large biomolecules such as proteins,
More informationChapter 20: Carboxylic Acids
1 Chapter 20: Carboxylic Acids I. Introduction: Carboxylic acid structure: Classification of carboxylic acids: A carboxylic acid donates protons by the heterocyclic cleavage of the O-H bond, generating
More informationAlabama Department of Postsecondary Education
Date Adopted: July 1, 1998 Date Reviewed: December 1, 1999 Date Revised: 1999, 2007, 2011 Alabama Department of Postsecondary Education Representing Alabama s Public Two-Year College System Jefferson State
More informationChapter 20 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution
Chapter 20 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Nomenclature: In carboxylic acid chlorides, anhydrides, esters and amides, the parent is the carboxylic acid. In each case be sure
More informationChapter 11 Reaction of Alcohols
Chapter 11 eaction of Alcohols xidation of alcohols Alcohols are at the same oxidation level as alkenes Therefore alkenes can be converted to alcohols with acidic water PDC or PCC 2 C C 2 3 + X 3 C 3 C
More informationADVANCED CHEMISTRY 2
ADVANCED CHEMISTRY 2 Philip Matthews ±m±l CAMBRIDGE UNIVERSITY PRESS Acknowledgements How to use this book INORGANIC CHEMISTRY 88 Periodicity of physical properties 88.1 Periodicity of ionisation energies
More informationOrganic Chemistry CHM 224
rganic Chemistry CM 224 Final Exam Review Questions This is a compilation example final exam questions. Provide IUPAC names for each of the structures below. 2 ! Propose a structure for the compound that
More informationReactions at α-position
Reactions at α-position In preceding chapters on carbonyl chemistry, a common reaction mechanism observed was a nucleophile reacting at the electrophilic carbonyl carbon site NUC NUC Another reaction that
More informationCourse Outline. TERM EFFECTIVE: Fall 2016 CURRICULUM APPROVAL DATE: 03/14/2016
5055 Santa Teresa Blvd Gilroy, CA 95023 Course Outline COURSE: CHEM 12B DIVISION: 10 ALSO LISTED AS: TERM EFFECTIVE: Fall 2016 CURRICULUM APPROVAL DATE: 03/14/2016 SHORT TITLE: ORGANIC CHEMISTRY LONG TITLE:
More informationPhysical organic chemistry
Physical organic chemistry Second edition Neil S. Isaacs Foreword to first edition Foreword to second edition Symbols and abbreviations Mechanistic designations vi i ix xxvi i xxvii r Models of chemical
More information16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 7 th edition
16. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry, 7 th edition Substitution Reactions of Benzene and Its Derivatives Benzene is aromatic: a cyclic conjugated
More informationCOURSE: ORGANIC CHEMISTRY
Página 1 de 7 GENERAL FEATURES* Type: Basic training, Mandatory, Elective Final degree project, External practices Duration: Annual Semester/s: 5 and 6 Number of credits ECTS: 12 Language/s: Spanish, Catalan,
More informationUNIT 4 REVISION CHECKLIST CHEM 4 AS Chemistry
UNIT 4 REVISION CHECKLIST CHEM 4 AS Chemistry Topic 4.1 Kinetics a) Define the terms: rate of a reaction, rate constant, order of reaction and overall order of reaction b) Deduce the orders of reaction
More informationChap 11. Carbonyl Alpha-Substitution Reactions and Condensation Reactions
Chap 11. Carbonyl Alpha-Substitution eactions and Condensation eactions Four fundamental reactions of carbonyl compounds 1) Nucleophilic addition (aldehydes and ketones) ) Nucleophilic acyl substitution
More informationPAPER No. 5: REACTION MECHANISM MODULE No. 2: Types of Organic Reaction Mechanisms
Subject Chemistry Paper No and Title Module No and Title Module Tag Paper No. 5:Organic Chemistry-II Module No. 2: Overview of different types of Organic Reaction Mechanisms CHE_P5_M2 TABLE OF CONTENTS
More informationSuggested solutions for Chapter 28
s for Chapter 28 28 PBLEM 1 ow would you make these four compounds? Give your disconnections, explain why you chose them and then give reagents for the. 2 2 Me S Exercises in basic one- group C X disconnections.
More informationLearning Guide for Chapter 11 - Alkenes I
Learning Guide for Chapter 11 - Alkenes I I. Introduction to alkenes - p 1 bond structure, classifying alkenes, reactivity, physical properties, occurrences and uses, spectroscopy, stabilty II. Unsaturation
More informationAdditions to the Carbonyl Groups
Chapter 18 Additions to the Carbonyl Groups Nucleophilic substitution (S N 2andS N 1) reaction occurs at sp3 hybridized carbons with electronegative leaving groups Why? The carbon is electrophilic! Addition
More informationChem 251 Fall Learning Objectives
Learning Objectives Chapter 8 (last semester) 1. Write an electron-pushing mechanism for an SN2 reaction between an alkyl halide and a nucleophile. 2. Describe the rate law and relative rate of reaction
More informationChapter 17: Alcohols and Phenols. Based on McMurry s Organic Chemistry, 7 th edition
Chapter 17: Alcohols and Phenols Based on McMurry s Organic Chemistry, 7 th edition Alcohols and Phenols Alcohols contain an OH group connected to a a saturated C (sp 3 ) They are important solvents and
More informationThis syllabus is printed on both sides of each page in the hard-copy version.
TO: FROM: Prospective Chemistry 5511 Students Peter Gaspar August 13, 2010 SUBJECT: Course Syllabus for Chemistry 5511 Fall 2010 Chemistry 5511 Mechanistic Organic Chemistry is the first semester of a
More informationFundamentals of. Organic Chemistry. for. [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester
Fundamentals of Organic Chemistry for [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester (This Book is an outcome of Modern Organic Chemistry by M.K. Jain & S.C. Sharma duly recommended
More informationChemistry of Benzene: Electrophilic Aromatic Substitution
Chemistry of Benzene: Electrophilic Aromatic Substitution Why this Chapter? Continuation of coverage of aromatic compounds in preceding chapter focus shift to understanding reactions Examine relationship
More informationChapter 19. Carbonyl Compounds III Reaction at the α-carbon
Chapter 19. Carbonyl Compounds III Reaction at the α-carbon There is a basic hydrogen (α hydrogen) on α carbon, which can be removed by a strong base. 19.1 The Acidity of α-hydrogens A hydrogen bonded
More informationORGANIC CHEMISTRY T. W. GRAHAM SOLOMONS. University of South Florida. JOHN WlLEY & SONS, INC. New York Chichester Brisbane Toronto Singapore
SIXTH EDITION ORGANIC CHEMISTRY T. W. GRAHAM SOLOMONS University of South Florida JOHN WlLEY & SONS, INC. New York Chichester Brisbane Toronto Singapore CONTENTS CHAPTER 1 CARBON COMPOUNDS AND CHEMICAL
More informationCONTENTS PART I STRUCTURES OF THE TRANSITION-METAL COMPLEXES
CONTENTS Introduction... 1 1. Organization of the text... 1 2. Frontiers of organometallic chemistry... 2 3. Situation of the book with respect to teaching... 2 4. Reference books and other selected references...
More information75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will
71. B SN2 stands for substitution nucleophilic bimolecular. This means that there is a bimolecular rate-determining step. Therefore, the reaction will follow second-order kinetics based on the collision
More information12.1 The Nature of Organic molecules
12.1 The Nature of Organic molecules Organic chemistry: : The chemistry of carbon compounds. Carbon is tetravalent; it always form four bonds. Prentice Hall 2003 Chapter One 2 Organic molecules have covalent
More information