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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:
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- Allows a “self-guided tour” of organic chemistry
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- Discusses all important areas and fundamental reactions of organic chemistry
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- Classroom tested
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- Useful as a study guide that will supplement most organic chemistry textbooks
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- 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
- 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
3.2Â ENERGETICS
3.3. THE ACIDITY CONSTANT, Ka
3.4. STRUCTURAL FEATURESÂ 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
10.1Â ORGANOMETALLICS
10.2. ORGANOMAGNESIUM COMPOUNDS
10.3Â 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
12.1Â 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
13.2Â OXIDATION OF ALKENES:Â 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
15.5Â 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
16.3Â 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
17.1Â Â 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
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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