Survival Guide to Organic Chemistry: Bridging the Gap from General Chemistry (Hardback) book cover

Survival Guide to Organic Chemistry

Bridging the Gap from General Chemistry

By Patrick E. McMahon, Bohdan B. Khomtchouk, Claes Wahlestedt

© 2016 – CRC Press

654 pages | 1751 B/W Illus.

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pub: 2016-12-01
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The Survival Guide to Organic Chemistry: Bridging the Gap from General Chemistry enables organic chemistry students to bridge the gap between general chemistry and organic chemistry. It makes sense of the myriad of in-depth concepts of organic chemistry, without overwhelming them in the necessary detail often given in a complete organic chemistry text.

Here, the topics covered span the entire standard organic chemistry curriculum. The authors describe subjects which require further explanation, offer alternate viewpoints for understanding and provide hands-on practical problems and solutions to help master the material. This text ultimately allows students to apply key ideas from their general chemistry curriculum to key concepts in organic chemistry.


'In Survival Guide to Organic Chemistry, the authors approach concepts in organic chemistry from an angle that differs from most textbooks. Rather than the usual approach of heavy paragraphs and figures, they establish a process wherein each concept is broken into a series of manageable steps, each of which involves a singular aspect of an overarching theme. Each step includes an example illustrating that singular process. This method allows students to approach material at levels within their control, rather than all at once for any given concept. The text also provides a framework for organizing reactions and includes over 30 practice exams spanning concepts of both semesters of a typical undergraduate organic chemistry sequence. In addition to students entering organic chemistry, this text could also serve as a useful reference for students in upper-level undergraduate or graduate level courses who need to refresh fundamental concepts before delving into more complex material. Finally, faculty may find this useful as a source of practice problems in class, as well as a means of guiding conversations for students struggling with particular concepts.

--J. Tedesco, Lake Erie College

Summing Up: Recommended. Lower-division undergraduates and above; faculty and professionals.'

J. Tedesco, for CHOICE, January 2018, Vol. 55, No. 5.

Table of Contents

Chapter 1

General Concepts for Covalent Bonding and Constructing Lewis Structures for Organic Molecules

Chapter 2

Guideline for Writing Organic Molecule Isomers and Determining Number of Rings Plus Pi-Bonds

Chapter 3

Guideline for Complete Analysis for Central Atoms and Molecules: Bonding/Hybridization/Geometry/Polarity

Chapter 4

Notation in Organic Chemistry: Guide to Writing and Using Condensed Formulas and Line Drawings

Chapter 5

Summary Guidelines for Organic Nomenclature

Chapter 6

Guidelines for Analysis of Intermolecular Forces for Organic Molecules

Chapter 7

Alkane and Cycloalkane Conformations

Chapter 8

Summary Guide to Thermodynamic Concepts for Organic Chemistry

Chapter 9

Guide to Kinetics and Reaction Mechanisms

Chapter 10

Review of Acid/Base Concepts for Organic Chemistry

Chapter 11

Electrophiles and Nucleophiles in Organic Reaction Mechanisms

Chapter 12

Conceptual Guide to Mechanisms in Organic Chemistry

Chapter 13

Guide to Stereochemistry Concepts and Analysis of Reaction

Stereochemistry as Applied to Electrophilic Addition


Chapter 14

A Process for Calculation of Product Distribution Through Relative Rate Analysis: Examples for Free Radical Halogenation

Chapter 15

Process to Identify and Solve the Reactions for Organic I

Chapter 16

Electrophilic Addition and Addition/Elimination to

Conjugated Double Bond and Aromatic Systems

Chapter 17

Oxidation/Reduction Relationships for Carbonyl Carbon

Chapter 18

A Complete System for Organizing, Identifying, and Solving Carbonyl Reactions: Nucleophilic Addition and Addition/Elimination

Chapter 19

A Brief Guideline for Applying Fundamental Concepts in NMR Spectroscopy


Organic I Practice Exams

Exams 1, 2

Organic Structure; Molecular Geometry; Hybridization

Exams 3, 4, 5

Alkanes/Cycloalkanes: Nomenclature, Properties, Conformations, Chirality, and Stereochemistry

Exams 6, 7, 8

Chirality and Diastereomers; Acid/Base Chemistry; Alkene Properties/Stereochemistry; Alkene and Alcohol Nomenclature


Exams 9, 10, 11

Kinetics and Thermodynamics; Mechanism Concepts; Alkene Reactions; Electrophilic Addition to Alkenes

Exams 12, 13, 14

Alkyl Halides: Free Radical Mechanisms; SN1 and SN2

Exams 15, 16, 17

Alkyl Halides and Alcohols: Reactions and Properties; SN1, SN2, E1, E2


Organic II Practice Exams

Exams 18, 19, 20

Reactions and Nomenclature of Alkynes; Electrophilic Addition to Conjugated Systems; Diels-Alder; Aromatic Molecules: Properties, Reactions, Electrophilic Aromatic Substitution

Exams 21, 22

Organometallic Reactions; Redox Reactions of Alcohols; Epoxides, Ethers; Nucleophilic Aromatic Substitution

Exams 23, 24

Carbonyl Chemistry; Aldehydes, Ketones; Carboxylic Acid Derivatives;

Nucleophilic Addition and Addition/Elimination

Exams 25, 26, 27

Enol and Enolate Anion Reactions of Carbonyls; Aldol and Claisen Condensations; α, β-Unsaturated Aldehydes; β-Ketoesters; Decarboxylation; Amine Chemistry

Multiple Choice Exams

Organic I: Multiple Choice Exam 1

Kinetics and Thermodynamics; Alkanes/Cycloalkanes: Nomenclature, Properties, Conformations, Chirality, and Stereochemistry

Organic I: Multiple Choice Exam 2

Stereochemistry; Alkene Reactions; Alkyl Halide and Alcohol Reactions: SN1, SN2, E1, E2, Radicals

Organic II: Multiple Choice Exam 1

Reactions and Nomenclature of Alkynes; Electrophilic Addition to Conjugated Systems; Diels-Alder; Aromatic Molecules: Properties, Reactions, Electrophilic Aromatic Substitution

Organic II: Multiple Choice Exam 2

Short Comprehensive Exam Written in the Style of a Standardized Exam

About the Authors

Patrick E. McMahon has for the past twenty three years been teaching both general chemistry and organic chemistry at Benedictine University in Lisle, Illinois. Prior to that, he was a research scientist for Amoco Chemical Company at the Naperville, Illinois campus. McMahon has also taught at several institutions in the Chicago area, including Elmhurst College, Dominican University and Triton Community College. He is a member of the American Legion and served in the United States Army from 1970-1972. His main area of research interest is organic reaction catalysis. Awards that can be accredited to his name include the B.J. Babler award for outstanding contribution to under-graduate instruction at the University of Illinois, the Dean’s Award for Teaching Excellence at Benedictine University and first recipient of the Shining Star award given by the student senate for outstanding contribution to students at Benedictine University.

Bohdan B. Khomtchouk is a triple-major summa cum laude (B.Sc. Biochemistry and Molecular Biology, B.Sc. Mathematics and B.Sc. Physics) and is currently United States Department of Defense NDSEG Fellow at the University of Miami Miller School of Medicine.

Claes Wahlestedt, MD, PhD, is Leonard M. Miller Professor at the University of Miami Miller School of Medicine and is working on a range of chemistry related translational efforts in his roles as Associate Dean and Center Director for Therapeutic Innovation. The author of some 250 peer reviewed scientific publications with 30,000+ citations, his ongoing research projects concern chemical biology, epigenetics, genomics and drug/biomarker discovery across several therapeutic areas. He has experience not only from academia, but also from leadership positions in the pharmaceutical industry, namely Astra-Zeneca, Pharmacia & Upjohn and Pharmacia Corporation.

Subject Categories

BISAC Subject Codes/Headings:
MEDICAL / Biochemistry
SCIENCE / Chemistry / Analytic
SCIENCE / Chemistry / Organic