I have been teaching Organic Chemistry for years and I know how overwhelming the material can get week after week and accumulate into a huge pile of headache source together with all the other classes during the exams’ week. I once was an undergrad going through this as well, and worse – ended up taking advanced organic synthesis (it was actually my favorite class) as a graduate student and that’s where I truly appreciated having the final set of a few summary pages to go over just before the test. Don’t get this concept wrong, you need to listen to your professor, take good notes and study by yourself. But having a final “so what, and which one” should I know out of all of these helps tremendously to focus, save time and get a higher grade.
I am currently a full-time faculty at South Texas College and you may wonder how I have managed to teach and put together these “cheat sheet” summary guides (hey, they take time, every single section of these guides took me hours of work to put as much as needed but not more than that so you won’t have to spend those hours to find the reagents necessary for carrying out functional group transformation or figuring out all the structural details in Organic 1). My answer is because I like it for myself and I enjoy doing it when I get a little break from teaching.
In this set of summary sheets, you will find the material covered in Org 1 and Org 2 courses including Resonance, Acids and Bases, Stereochemistry, Reactions of Alkenes, Alkynes, Alcohols, Aromatic compounds, a simple diagram that will finally answer the question of SN1, SN2, E1 or E2 and more. There is also a summary guide of a practical approach to solving IR problems with a worked example following three important steps. These summary sheets are comprehensive and cover most of what is taught for that topic in undergraduate organic chemistry courses.
Organic chemistry summary sheets will also help you prepare for MCAT, PCAT, DAT, ACS, and other tests.
Organic Chemistry 1 and 2 Study Guides Include
1. Lewis Structures, Resonance Structures, and Formal Charges
Following a few steps to draw Lewis structures, Formal Charges, and a table to quickly identify them, Resonance Structures, Resonance hybrid, Curved Arrows and the rules for drawing resonance Structures, a Complete Guide for Assessing the Relative Importance of Resonance Structures considering all the factors for stability of cations and anions.
2. Geometry and Hybridization
A shortcut to Predicting Electron and Molecular Geometry (VSEPR Theory) accompanied with a chart for all the possibilities geometries in Organic Chemistry. Hybridization and Hybrid Orbitals: understand the bond types and angles as well as a shortcut to quickly determine the sp3, sp2, and sp hybridization.
3. Functional Groups
This is going to be the organic chemistry alphabet. The sooner you learn to recognize alcohols, amines, alkenes, aromatic compounds, aldehydes, ketones, esters, and some others, the easier starting organic chemistry will be. This is a two-page summary of the most common organic functional groups with examples and their application.
4. Molecular Representations (Converting between Bond-line, Lewis and Condensed structures)
One of the foundations and a key transition from General to Organic Chemistry is the deep insight of molecular structures and learning the concept of Bond-Lile (Zig-Zag representation). Here is the much-needed to-the-point summary linking the Bond-line, Lewis and Condensed structures!
5. Bond Characteristics-Types, Length, Strength, and Dipole Moment
This document summarizes the types of chemical bonds and their properties such as length, strength, polarity, dipole moment, partial charges, and molecular polarity. A shortcut to determining whether an ionic, nonpolar, or polar covalent bond is formed, how the dipole moments are characterized, how to determine if the molecule is polar overall, how to determine the stronger bond depending on the atomic size and hybridization!
6. Intermolecular Interactions and Physical Properties
This two-page guide will be a handy summary of the intermolecular interactions such as ionic bonds, hydrogen bonds, dipole-dipole interactions, London dispersion forces, their relative strength, and their relation to the boiling and melting points. The specific examples on page two will give you a pattern for determining the compound with a higher boiling or melting point.
7. Acids and Bases
It wouldn’t be an exaggeration to state that you can’t master Organic Chemistry without a good understanding of Acid-Base Chemistry.
This summary guide will give all you need to know in this essential chapter: Overview of Acids and Bases – Arrhenius, Brønsted, and Lewis acid-base definitions, Acid Strength and the concept of pKa, What makes a Strong Acid and a Base – all the factors discussed in their priority; atoms, charges, resonance, induction, orbitals, aromaticity. The Position of Equilibrium for an Acid-Base Reaction, Choosing an Acid or a Base to protonate and deprotonate a compound, the Henderson-Hasselbalch Equation
8. An Introduction to Nomenclature and IUPAC Rules
This study guide summarizes the names of alkanes and alkyl groups such as butyl, iso-butyl, tert-butyl, and their use in the IUPAC rules for systematic nomenclature.
A walkthrough of finding the substituents, the parent chain with possible complications is designed to set a good foundation for the naming strategies that are used throughout the chapters of Organic 1 and 2.
9. Conformations of Alkanes and Cycloalkanes
Conformations, conformers, and conformational isomers, Newman projections, Staggered and Eclipsed conformations, Torsional and Steric strain, Conformations of Cycloalkanes, the Chair conformation, Ring-Flip, Calculating the energy of a Chair conformation.
10. Stereochemistry and Chirality
Isomerism, Constitutional and Stereoisomers, Enantiomers and Diastereomers, Chirality, Absolute configuration by the R and S system, R and S in the Fischer projection, Optical Activity, Symmetry and chirality, Meso compounds, R and S configuration of Fischer projections, and an extremely handy graphical summary of converting between Bond-line, Newman, and Fischer projections.
11. Nucleophilic Substitution – SN1 an SN2
An overview of Substitution Reactions, identifying the nucleophile, electrophile and the leaving group. The SN2 Mechanism, The SN1 Mechanism, kinetic and thermodynamic parameters of both mechanisms, Reactivity of Substrates (alkyl halides) in SN2 and SN1 Reactions, inductive effect, and hyperconjugation. What Makes a Good Nucleophile? The Role of the Solvent On Nucleophilicity. What Makes a Good Leaving Group?
12. Elimination Reactions – E1 and E2
General Features of Elimination Reactions, The E2 and E1 Mechanisms, the Regioselectivity of E2 and E1 Reactions, Stereoselectivity of E2 and E1
Reactions, Stereospecificity of E2 Reactions, E2 Reactions of Cyclohexanes, the kinetics and Reactivity of Substrates in E2 and E1 Reactions, Rearrangements in E1 and SN1 Reactions, Elimination Reactions of Alcohols, How to Know if the Reaction is E1 or E2, The E1CB Mechanism.
13. Competition in Substitution and Elimination Reactions; SN1/E1 vs SN2/E2
I know we all have to deal with this at one point. Is it SN1, SN2, E1 or none of these it is actually E2…?
You will find the quickest way of determining the SN1 vs SN2 and E1 vs E2 competition and a flow-chart to figure out the mechanism out of the SN1, SN2, E1 and E2 combination. Yes, it is possible to summarize in one simple chart!
Benzylic and Allylic Halides are included as well.
14. Reactions of Alkenes
All the reactions of alkenes, starting from the Addition of Hydrogen halide (HX), Hydroboration-Oxidation, Ozonolysis, and all the way to the Simmons–Smith reaction including the mechanism and the regio– and stereochemistry of the reaction where it is applicable.
15. Reactions of Alkynes
Just like for the alkenes, a summary and the mechanisms of all the reactions including hydration, hydrohalogenation, hydroboration, reduction, and oxidative cleavage, plus the acid-base chemistry of terminal alkynes and their synthetic applications.
16. Reactions of Alcohols
First of all, a chart summarizing the Preparation of Alcohols from carbonyl compounds such as Aldehydes, Ketones, Esters, Acids, and Acid Chloride using LiAlH4, NaBH4, Raney Ni, Pd/C, DIBAL-H, and by the Grignard Reaction. Save the time to look them up one-by-one! Additionally, you will have the summary of preparing alcohols By Addition Reaction to Alkenes and Substitution Reactions.
Oxidation of Alcohols: What to expect from the oxidation of primary, secondary, and tertiary alcohols by the most common oxidizing agents such as Na2Cr2O7/ H2SO4, H2CrO4, CrO3/ H+, KMnO4/ -OH/ H+, NaClO/ AcOH.
How to selectively oxidize alcohols to aldehydes using PCC (Pyridinium Chlorochromate), PDC (Pyridinium Dichromate), Swern (DMSO, (COCl)2, Et3N), and DMP (Dess-Martin) oxidizing agents.
Alcohols in Substitution and Elimination Reactions. This will cover the reactions where the alcohols are nucleophiles, electrophiles, and bases. All the possibilities of doing substitution and elimination reactions by SN2, SN1, E2 and E1 mechanisms. A sum up for the approaches for converting the OH into a good leaving group and using it to prepare alkenes by Zaitsev and Hoffman reactions. The use of SOCl2, PBr3, POCl3 for substitution and elimination of alcohols and finally the Protecting Groups for Alcohols in organic synthesis.
17. Reactions of Amines and Epoxides
A summary of the most common ways of preparations and reactions of amines.
The Gabriel Synthesis, amination of alkyl halides, reduction of nitrogen-containing derivatives, reaction with aldehydes and ketones, reductive amination, preparation of arene diazonium salts, and more.
A summary of the preparation and reactions of epoxides.
Peroxy acids and halohydrins, ring-opening reactions with strong and weak nucleophiles. How does the ring open, where does the nucelopiule go, what happens to the stereochemistry of both carbons when the epoxide is chiral?
Mechanism, regiochemistry, stereochemistry – it’s all here.
18. The Diels-Alder Reaction
Diels-Alder reaction summarized in two comprehensive pages. This includes the introduction, common key features, the mechanism, the stereochemistry and Regiochemistry of the reaction. Th Endo-Exo products applied for both cyclic and acyclic dienes (in case you go that far in your class). This summary guide will leave no unanswered questions on the Diels-Alder reaction.
19. Reactions of Aromatic Compounds
Electrophilic Aromatic Substitution: the key reactions and alternative approaches to Changing the Common Substituents. The Mechanism of Electrophilic Aromatic Substitution, the Friedel-Crafts reactions, Activating and Deactivating Groups, Ortho-, Para- and Meta– Positions and Directors. Ortho-, Para- and Meta- in Disubstituted Rings: How to synthesize a di- or tri-substituted benzene ring by adding the groups in the correct order. Reactions of Arenediazonium Salt and the Limitations of Electrophilic Aromatic Substitution Reactions – what reactions and strategies do not work and how to overcome these obstacles.
20. Reactions of Aldehydes and ketones
Nucleophilic Additions to the Carbonyl Group: general consideration of steric and electronic effects. Summary of Common Nucleophilic Addition Reactions including those with water, alcohols, thiols, and amines. Acetals and hemiacetals and application in organic synthesis, reductive amination, The Wittig Reaction, Protecting Groups for Aldehydes and Ketones, Reduction of Aldehydes and Ketones using LiAlH4 NaBH4 Raney Ni, Pt/H2 and DIBAL-H.
Reactions with Organolithiums and Grignard reagent, 1,2- and 1,4-Additions, The Baeyer-Villiger oxidation
21. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
This beautiful Summary Guide includes the Nucleophilic Acyl Substitution mechanism also referred to as an Addition-Elimination mechanism, the mechanism of Fischer esterification.
The reaction of esters such as reversible hydrolysis under acidic and irreversible hydrolysis under basic conditions, transesterification, and all the others with nucleophiles and reducing agents.
You will have a comprehensive summary of the preparation and all the major reactions of Carboxylic Acids, Anhydrides, Esters, Acid (acyl) Chlorides, Amides and Nitriles. All the common patterns, as well as the details for specific reactions for example with the Grignard reagent and Organocuprates of each derivative, are addressed in the given section.
22. Alpha Carbon Chemistry: Enols and Enolates
In this 3-page summary of the Alpha carbon chemistry, you will find the key concepts and reactions of enols and enolates such as the Thermodynamic and Kinetic Enolates and their most important reactions. It also summarizes the alkylation and condensation reactions such as the Aldol reaction, the Claisen reaction, Robinson annulation, Stork Enamine synthesis, Malonic Ester Synthesis, Acetoacetic Ester Synthesis, Michael Addition, and some more.
23. Carbohydrates
A comprehensive, easy-to-follow two-page summary of the Structure, Stereochemistry, and Key Reactions of carbohydrates. Aldoses, ketoses, treoses, tetroses and etc. Everything about the D and L notation of sugars and its relationship to the R and S system and optical rotation. Definition of Anomers and Epimers, α- and β-glucose and their representation in cyclic forms. You won’t look at the carbohydrates the same way again!
24. IR Spectroscopy
1. How to Solve IR Problems in 3 steps
IR spectra look crowded and overcomplicated at first but this summary guide will change your view on this!
25. NMR Spectroscopy
2. NMR Spectroscopy – 5 pages that include
- Chemical Shift and Integration
- Number of NMR signals
- Spin-Spin Splitting (Multiplicity) of the NMR signal
- 13C NMR Spectroscopy
- How to Determine the Structure of an Unknown Using 1H NMR
These are beautiful, comprehensive, and meticulously written summaries. I spent a week putting together each page that will recap and settle all the information you get overwhelmed with before you go to the exam.
Chemical shifts, integration, signal-splitting, coupling constants, 13C NMR, DEPT, and 2D-NMR all in one place.
In addition, you will get one page of practical steps for solving NMR problems.
Organic Chemistry 1 and 2
$34 $23
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Organic Chemistry 1 and 2 Study Guides
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