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A Q&A Approach to Organic Chemistry




ISBN 9780367224271
Published June 2, 2020 by CRC Press
524 Pages 100 B/W Illustrations

 
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Book Description

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

CHAPTER ONE.  ORBITALS AND BONDING

 

1.1 ORBITALS

                1.1.A.  ATOMIC ORBITALS

                1.1.B. ELECTRON CONFIGURATION

                1.1.C. MOLECULAR ORBITALS

1.2 BONDING

                1.2.A. IONIC BONDING

                1.2.B. COVALENT BONDING

1.3 HYBRIDIZATION

1.4. RESONANCE

END 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

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Author(s)

Biography

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.