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A Q&A Approach to Organic Chemistry
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A Q&A Approach to Organic Chemistry

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PDF

Author(s)

Michael B. Smith

Publisher

CRC Press

ISBN-10

0367224275

ISBN-13

978-0367224271

Pages

538

Language

English

Edition

1st edition | June 3, 2020

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8 MB

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  • Description
Description

A Q&A Approach to Organic Chemistry

A Q&A Approach to Organic Chemistry 1st Edition:

A Q&A Approach to Organic Chemistry is a book of leading questions that begins with atomic orbitals and bonding. All critical topics are covered, including bonding, nomenclature, stereochemistry, conformations, acids and bases, oxidations, reductions, substitution, elimination, acyl addition, acyl substitution, enolate anion reactions, the Diels–Alder reaction and sigmatropic rearrangements, aromatic chemistry, spectroscopy, amino acids and proteins, and carbohydrates and nucleosides. All major reactions are covered. Each chapter includes end-of-chapter homework questions with the answer keys in an Appendix at the end of the book. This book is envisioned to be a supplementary guide to be used with virtually any available undergraduate organic chemistry textbook. This book allows for a “self-guided” approach that is useful as one studies for a coursework exam or as one reviews organic chemistry for postgraduate exams.

Key Features:

    • Allows a “self-guided tour” of organic chemistry
    • Discusses all important areas and fundamental reactions of organic chemistry
    • Classroom tested
    • Useful as a study guide that will supplement most organic chemistry textbooks
    • Assists one in study for coursework exams or allows one to review organic chemistry for postgraduate exams
  • Includes 21 chapters of leading questions that covers all major topics and major reactions of organic chemistry

Table of Contents

Contents

  • 1.1 ORBITALS1.1.A.  ATOMIC ORBITALS1.1.B. ELECTRON CONFIGURATION1.1.C. MOLECULAR ORBITALS1.2 BONDING1.2.A. IONIC BONDING1.2.B. COVALENT BONDING1.3 HYBRIDIZATION1.4. RESONANCEEND OF CHAPTER PROBLEMS

    CHAPTER TWO.  STRUCTURE OF MOLECULES

    2.1.  BASIC STRUCTURE OF ORGANIC MOLECULES

    2.1.A.  Fundamental Structures

    2.1.B.  Structures With Other Atoms Bonded to Carbon

    2.2. THE VSEPR MODEL AND MOLECULAR GEOMETRY

    2.3.  DIPOLE MOMENT

    2.4.  FUNCTIONAL GROUPS

    2.5.  FORMAL CHARGE

    2.6. PHYSICAL PROPERTIES

    END OF CHAPTER PROBLEMS.

    CHAPTER THREE.  ACIDS AND BASES

    3.1 ACIDS AND BASES

    3.2  ENERGETICS

    3.3. THE ACIDITY CONSTANT, Ka

    3.4. STRUCTURAL FEATURES  THAT INFLUENCE ACIDITY

    3.5.  FACTORS THAT CONTRIBUTE TO MAKING THE ACID MORE ACIDIC

    END OF CHAPTER PROBLEMS

    CHAPTER FOUR.  ALKANES, ISOMERS, AND NOMENCLATURE

    4.1. DEFINITION AND BASIC NOMENCLATURE

    4.2. STRUCTURAL ISOMERS

    4.3. IUPAC NOMENCLATURE

    4.4. CYCLIC ALKANES

    END OF CHAPTER PROBLEMS

    CHAPTER FIVE. CONFORMATIONS

    5.1. ACYCLIC CONFORMATIONS

    5.2. CONFORMATIONS OF CYCLIC MOLECULES

    END OF CHAPTER PROBLEMS

    CHAPTER SIX. STEREOCHEMISTRY

    6.1. CHIRALITY

    6.2. SPECIFIC ROTATION

    6.3. SEQUENCE RULES

    6.4. DIASTEREOMERS

    6.5. OPTICAL RESOLUTION

    END OF CHAPTER PROBLEMS

    CHAPTER SEVEN. ALKENES AND ALKYNES:

    STRUCTURE, NOMENCLATURE AND REACTIONS

    7.1. STRUCTURE OF ALKENES

    7.2. NOMENCLATURE OF ALKENES

    7.3.  REACTIONS OF ALKENES

    7.4. REACTION OF ALKENES WITH LEWIS ACID REAGENTS

    7.4.A. Hydroxylation

    7.4.B. Epoxidation

    7.4.C. Dihydroxylation

    7.4.D. Halogenation

    7.4.E. Hydroboration

    7.5. STRUCTURE AND NOMENCLATURE OF ALKYNES

    7.6 . REACTIONS OF ALKYNES

    END OF CHAPTER PROBLEMS

    CHAPTER EIGHT.  ALKYL HALIDES AND SUBSTITUTION REACTIONS

    8.1.  STRUCTURE, PROPERTIES AND NOMENCLATURE OF ALKYL HALIDES

    8.2. SECOND ORDER NUCLEOPHILIC SUBSTITUTION (SN2) REACTIONS

    8.3.  OTHER NUCLEOPHILES IN SN2 REACTIONS

    8.4. FIRST ORDER NUCLEOPHILIC SUBSTITUTION (SN1) REACTIONS

    8.5.  COMPETITION BETWEEN SN2 VS. SN1 REACTIONS

    8.6.  RADICAL HALOGENATION OF ALKANES

    END OF CHAPTER PROBLEMS

    CHAPTER NINE. ELIMINATION REACTIONS

    9.1. THE E2 REACTION

    9.2. THE E1 REACTION

    9.3. PREPARATION OF ALKYNES

    9.4. SYN ELIMINATION

    END OF CHAPTER PROBLEMS

    CHAPTER TEN. ORGANOMETALLIC COMPOUNDS

    10.1  ORGANOMETALLICS

    10.2.  ORGANOMAGNESIUM COMPOUNDS

    10.3  ORGANOLITHIUM COMPOUNDS

    10.4.  BASICITY

    10.5.  REACTION WITH EPOXIDES

    10.6.  OTHER METALS

    END OF CHAPTER PROBLEMS

    CHAPTER ELEVEN. SPECTROSCOPY

    11.1. THE ELECTROMAGNETIC SPECTRUM

    11.2. MASS SPECTROMETRY (MS)

    11.3. INFRARED SPECTROSCOPY (IR)

    11.4. NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY (NMR)

    End of Chapter Problems

    CHAPTER TWELVE. ALDEHYDES AND KETONES.  ACYL ADDITION REACTIONS

    12.1  STRUCTURE AND NOMENCLATURE OF ALDEHYDES AND KETONES

    12.2. REACTION OF ALDEHYDES AND KETONES WITH WEAK NUCLEOPHILES

    12.3.  REACTIONS OF ALDEHYDES AND KETONES.  STRONG NUCLEOPHILES

    12.4.  THE WITTIG REACTION

    END OF CHAPTER PROBLEMS

    CHAPTER THIRTEEN. OXIDATION REACTIONS

    13.1.  OXIDATION REACTIONS OF ALKENES

    13.2  OXIDATION OF ALKENES:  EPOXIDATION

    13.3.  OXIDATIVE CLEAVAGE: OZONOLYSIS

    13.4.  OXIDATIVE CLEAVAGE.   PERIODIC ACID CLEAVAGE OF 1,2-DIOLS

    13.5.  OXIDATION OF ALCOHOLS TO ALDEHYDES OR KETONES

    END OF CHAPTER PROBLEMS

    CHAPTER FOURTEEN.  REDUCTION REACTIONS

    14.1. CATALYTIC HYDROGENATION

    14.2. DISSOLVING METAL REDUCTION: ALKYNES

    14.3.  HYDRIDE REDUCTION OF ALDEHYDES AND KETONES

    14.4.  CATALYTIC HYDROGENATION AND DISSOLVING METAL REDUCTIONS. ALDEHYDES AND KETONES

    End of Chapter Problems

    CHAPTER FIFTEEN. CARBOXYLIC ACIDS, CARBOXYLIC ACID DERIVATIVES

    AND ACYL SUBSTITUTION REACTIONS

    15.1.  STRUCTURE OF CARBOXYLIC ACIDS

    15.2.  PREPARATION OF CARBOXYLIC ACIDS

    15.3.  CARBOXYLIC ACID DERIVATIVES

    15.4.  PREPARATION OF ACID DERIVATIVES

    15.5  HYDROLYSIS OF CARBOXYLIC ACID DERIVATIVES

    15.6.  REACTIONS OF CARBOXYLIC ACIDS AND ACID DERIVATIVES

    15.7.  DIBASIC CARBOXYLIC ACIDS

    END OF CHAPTER PROBLEMS

    CHAPTER SIXTEEN. BENZENE, AROMATICITY, AND BENZENE DERIVATIVES

    16.1. BENZENE AND NOMENCLATURE OF AROMATIC COMPOUNDS

    16.2.  ELECTROPHILIC AROMATIC SUBSTITUTION

    16.3  SYNTHESIS VIA AROMATIC SUBSTITUTION

    16.4.  NUCLEOPHILIC AROMATIC SUBSTITUTION

    16.5.  REDUCTION OF BENZENE AND BENZENE DERIVATIVES

    16.6.  POLYCYCLIC AROMATIC COMPOUNDS AND HETEROAROMATIC COMPOUNDS

    END OF CHAPTER PROBLEMS

    CHAPTER SEVENTEEN. ENOLATE ANIONS AND CONDENSATION REACTIONS

    17.1   ALDEHYDES, KETONES, ENOLS, AND ENOLATE ANIONS

    17.2.   ENOLATE ALKYLATION

    17.3. CONDENSATION REACTIONS OF ENOLATE ANIONS AND ALDEHYDES OR KETONES

    17.4.  ENOLATE ANIONS FROM CARBOXYLIC ACIDS AND DERIVATIVES

    END OF CHAPTER PROBLEMS

    CHAPTER EIGHTEEN. CONJUGATION AND

    REACTIONS OF CONJUGATED COMPOUNDS

    18.1. CONJUGATED MOLECULES

    18.2. STRUCTURE AND NOMENCLATURE OF CONJUGATED SYSTEMS

    18.3.  REACTIONS OF CONJUGATED MOLECULES

    18.4.  THE DIELS-ALDER REACTION

    18.5.  [3+2]-CYCLOADDITION REACTIONS

    18.6.  SIGMATROPIC REARRANGEMENTS

    18.7. ULTRAVIOLET SPECTROSCOPY

    END OF CHAPTER PROBLEMS

    CHAPTER NINETEEN. AMINES

    19.1. STRUCTURE AND PROPERTIES

    19.2.  PREPARATION OF AMINES

    19.3. REACTIONS OF AMINES

    19.4. HETEROCYCLIC AMINES

    END OF CHAPTER PROBLEMS

    CHAPTER TWENTY. AMINO ACIDS, PEPTIDES AND PROTEINS

    20.1 AMINO ACIDS

    20.2. SYNTHESIS OF AMINO ACIDS

    20.3. REACTIONS OF AMINO ACIDS

    20.4. PROTEINS

    END OF CHAPTER PROBLEMS

    CHAPTER TWENTY-ONE.  CARBOHYDRATES AND NUCLEIC ACIDS

    21.1.  CARBOHYDRATES

    21.2. DISACCHARIDES AND POLYSACCHARIDES

    21.3. SYNTHESIS OF CARBOHYDRATES

    21.4. REACTIONS OF CARBOHYDRATES

    21.5. NUCLEIC ACIDS, NUCLEOTIDES AND NUCLEOSIDES

    END OF CHAPTER PROBLEMS

    ANSWERS TO END OF CHAPTER PROBLEMS

About the Authors

Professor Michael B. Smith was born in Detroit, Michigan in 1946 and moved to Madison Heights, Virginia in 1957, where he attended high school at Amherst County High School. He received an A.A. from Ferrum College in 1967 and a B.S. in chemistry from Virginia Polytechnic Institute in 1969. After working for three years at the Newport News Shipbuilding and Dry Dock Co. in Newport News VA as an analytical chemist, he entered graduate school at Purdue University. He received a Ph.D. in Organic chemistry in 1977, under the auspices of Professor Joe Wolinsky. Professor Smith spent one year as a faculty research associate at the Arizona State University with Professor G. Robert Pettit, working on the isolation of cytotoxic principles from plants and sponges. He spent a second year of postdoctoral work with Professor Sidney M. Hecht at the Massachusetts Institute of Technology, working on the synthesis of bleomycin A2.

Professor Smith began his academic career at the University of Connecticut in 1979, where he achieved the rank of professor of chemistry. In 1986 he spent a sabbatical leave in the laboratories of Professor Leon Ghosez, at the Université Catholique de Louvain in Louvain-la-Neuve, Belgium, as a visiting professor. He retired as a full professor from the University of Connecticut on January 1, 2017, and is currently pursuing his interests as an author.

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