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Organic Chemistry For the MCAT
Last updated: October 5th, 2022 |
Many students taking organic chemistry one day plan to write the Medical College Admission Test (MCAT). A common question students have for me is what type of thinking is required in order to do well on this exam. I plead ignorance, so to help educate myself and others I am happy to present an expert in this area, who will merely go by the name “Org Chem Prof” for our purposes. Dr. Org Chem Prof has kindly offered to write a guest post on MOC to describe the key features of organic chemistry for the MCAT . I hope this gives you a sense of what to expect.
Organic Chemistry For The MCAT, by “OrgChemProf”
Background.: Since most (if not all) U. S. medical schools require applicants to take the Medical College Admission Test (MCAT), this exam often represents the last hurdle that an aspiring medical school applicant must overcome in order to begin to fulfill his or her ambitions. A huge amount of information is available that is designed to help students prepare to take the examination; I defer to the expertise of the many authors who offer this assistance.
My own involvement with MCAT stems from long experience as a reviewer and content provider to the agency that prepares materials for inclusion in the Organic and Bio-organic Chemistry sections of the MCAT examination. My purpose in writing this brief essay is to share some of my experience with students who plan to take the MCAT exam and who wish to gain some relevant philosophical insight and possibly also some practical insight. Since my experience is necessarily limited, I shall confine my remarks to the Organic Chemistry portion of MCAT.
Why Do Medical Schools Rely Upon MCAT? Students should understand that medical schools seek to admit applicants who can demonstrate the ability to think independently and to reason critically. As a result the MCAT examination does more than simply test an examinee’s knowledge of a particular subject.
One should consider the situation from the standpoint of the medical school’s admissions committee. They are deluged with applications that appear, at least on paper, to have been tendered by outstanding students.
In the case of any one particular applicant, how can the members of the committee be reasonably assured that their faculty’s investment of time, instructional effort and materials ultimately will be rewarded? Training future MDs is an expensive business; so the admissions committee can’t afford to make many mistakes. That’s where the MCAT comes into play.
The bottom line: High achievement on the MCAT, when taken together with solid personal recommendations and an impressive grade point average in university coursework (and other factors too numerous and too nebulous to mention), is considered to offer a reliable predictor of the applicant’s suitability to pursue a career in medicine and potential for eventual success.
Mechanics and Philosophy. A typical Organic Chemistry unit consists of a ca. 250 word narrative passage followed by 10 questions that are related to topics, experimental results, and/or conclusions that either are presented or discussed explicitly in the passage or can be inferred from information contained therein.
The narrative passage might present research results and also might include conclusions derived from the experimental results. Alternatively, the passage might simply present information about a particular reaction or set of reactions. Occasionally the passage will present arguments to favor one reaction mechanism relative to other alternative mechanisms, in which case examinees are likely to be asked to evaluate those arguments.
Questions generally are related in one way or another to the content of the passage. Occasionally the questions are straightforward and rely primarily upon an examinee’s knowledge of the subject gained from Organic Chemistry lecture and laboratory courses. In this case, the examinee will be required to apply that knowledge to new or unfamiliar situations.
Then there is another type of question that generally requires a higher level of understanding of the subject matter contained within the passage. Questions of this type may require examinees to predict the outcome of a reaction or set of reactions based upon information contained in the passage. Other questions of this type may require examinees, e. g., to evaluate experimental results, to interpret graphical or pictorial representations of results, to interpret absorption spectra (UV, IR, NMR) or perhaps to evaluate conclusions derived from experimental results. Examinees may be asked to recognize a set of conditions that can be used to differentiate among mechanistic alternatives.
Can You Give Me An Example? Sure! I have prepared a sample unit that deals with the topic of nucleophilic substitution in allylic systems. The ten questions that accompany the narrative offer varying degrees of difficulty and probe different aspects of the information and conclusions presented in the passage.
Sample Organic Chemistry MCAT Passage and Exam Questions
Topic: Nuceophilic Substitution in Allylic Systems
The stereochemistry of nucleophilic substitution reactions that involve allylic halides and alllylic alcohols as substrates has been studied extensively.
Results of Experiment 1: Reaction of optically active cis-5-methylcyclohexen-3-ol (Compound 1) with thionyl chloride in dry diethyl ether was found to afford optically active cis-3-chloro-5-methylcyclohexene (Compound 2) as the exclusive reaction product. The absolute configurations of Compounds 1 and 2 are shown in Figure 1.
Figure 1. Reaction of optically active cis-5-methylcyclohexen-3-ol with thionyl chloride
Results of Experiment 2: Acetolysis of optically active trans-3-chloro-5-methylcyclohexene (Compound 3) was allowed to proceed through one reaction half-life. The reaction mixture then was quenched, and the starting material was isolated. Compound 3 thereby recovered was found to have racemized.
Results of Experiment 3: The kinetics of acetolysis of optically active trans-3-chloro-5-methylcyclohexene (Compound 3) were followed through several half-lives. The rate of racemization of Compound 3 was found to be more than four times the corresponding rate of acetolysis. Solvolysis resulted in the formation of racemic cis-3-acetoxy-5-methylcyclohexene (Compound 4, Figure 2).
Figure 2. Acetolysis of optically active trans-3-chloro-5-methylcyclohexene
Question 1. Which of the following conclusions is consistent with the results of Experiment 1 cited in the passage?
A. Compound 2 is formed via SN2 displacement of OS(O)Cl by Cl– with inversion of configuration at C-3.
B. Compound 2 is formed via SNi displacement of OS(O)Cl by Cl– with retention of configuration at C-3.
C. Compound 2 is formed via SN2′ displacement of OS(O)Cl by Cl– with concomitant allylic rearrangement.
D. Compound 2 can result either via SNi or SN2′ displacement of OS(O)Cl by Cl–.
Question 2. Which of the following statements is most consistent with the results of Experiment 2 cited in the passage?
A. The reaction proceeds via formation of a chiral carbocation that subsequently reacts with HOAc with concomitant racemization.
B. The reaction proceeds via formation of an achiral carbocation.
C. Homolysis of the C-Cl bond in Compound 3 results in the formation of an allylic radical.
D. The reaction proceeds via formation of an achiral radical.
Question 3. Which of the following statements as applied to the reaction mechanism indicated below is most consistent with the results of Experiment 3 cited in the passage?
A. A chiral intermediate is formed reversibly during acetolysis of Compound 3; the relative rates of disappearance of this intermediate: k2 < k-1.
B. A chiral intermediate is formed reversibly during acetolysis of Compound 3; the relative rates of disappearance of this intermediate: k2 > k-1.
C. An achiral intermediate is formed reversibly during acetolysis of Compound 3; the relative rates of disappearance of this intermediate: k2 < k-1.
D. An achiral intermediate is formed reversibly during acetolysis of Compound 3; the relative rates of disappearance of this intermediate: k2 > k-1.
Question 4. The absolute configuration of optically active Compound 3 is shown in Figure 2. What are the Cahn-Ingold-Prelog R,S designations of carbon atoms C-3 and C-5 in this molecule?
A. 3R, 5R
B. 3R, 5S
C. 3S, 5R
D. 3S, 5S
Question 5. Compound 1 is allowed to react with hydrogen gas over palladized charcoal, and aliquots are withdrawn at various reaction time intervals. What change(s) in appearance of the infrared spectrum of the reaction mixture are expected to occur as the reaction progresses?
A. Absorption signals at 3060 cm-1 and at 1660 cm-1 become less intense as the reaction progresses.
B. Absorption signal at 3060 cm-1 becomes more intense, while the absorption signal at 1660 cm-1 becomes less intense.
C. Absorption signal at 1660 cm-1 becomes more intense, while the absorption signal at 3060 cm-1 becomes less intense.
D. Absorption signals at 3060 cm-1 and at 1660 cm-1 become more intense as the reaction progresses.
Question 6. Which specifically-deuterated optically active substrate could be used to determine whether the reaction discussed in Experiments 2 and 3 proceed with or without concomitant allylic rearrangement?
Question 7. Which series represents the correct order of 1H chemical shifts (1 = highest field, 3 = lowest field) of the indicated protons in the proton NMR spectrum of cis-3-chloro-5-methylcyclohexene (Compound 2)?
Question 8. The reaction of diethylamine with α-methylallyl chloride, which affords Compound 5, is first order in both reactants. Both α-methylallyl chloride and Compound 5 are stable under the reaction conditions employed. What is most likely to be the rate-determining step of this reaction?
A. Nucleophilic attack by diethylamine at the α-carbon atom in α-methylallyl chloride
B. Nucleophilic attack by diethylamine at the β-carbon atom in α-methylallyl chloride
C. Nucleophilic attack by diethylamine at the γ-carbon atom in α-methylallyl chloride
D. Heterolysis of the C-Cl bond in α-methylallyl chloride
Question 9. Consider again the reaction of diethylamine with α-methylallyl chloride, which affords Compound 5. What change in hybridization occurs at the α-carbon atom in α-methylallyl chloride as a result of this reaction?
A. sp → sp2
B. sp2 → sp
C. sp2 → sp3
D. sp3 → sp2
Question 10. In general, alcohols are not useful as substrates for bimolecular nucleophilic substitution reactions. Reaction of a primary alcohol, R-OH with which one of the following reagents affords a derivative that is suitable substrate for bimolecular nucleophilic substitution reaction with NaI?
Reality Check. In order to maximize the effectiveness of the sample unit I recommend strongly that you first work through the entire examination without looking at the answers and accompanying explanations. In this way some clarification of the philosophical points discussed above may emerge after you have subjected yourself to a practice session that resembles actual test conditions.
Wishing you the best of success in all endeavors.
00 General Chemistry Review
01 Bonding, Structure, and Resonance
- How Do We Know Methane (CH4) Is Tetrahedral?
- Hybrid Orbitals and Hybridization
- How To Determine Hybridization: A Shortcut
- Orbital Hybridization And Bond Strengths
- Sigma bonds come in six varieties: Pi bonds come in one
- A Key Skill: How to Calculate Formal Charge
- Partial Charges Give Clues About Electron Flow
- The Four Intermolecular Forces and How They Affect Boiling Points
- 3 Trends That Affect Boiling Points
- How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge)
- Introduction to Resonance
- How To Use Curved Arrows To Interchange Resonance Forms
- Evaluating Resonance Forms (1) - The Rule of Least Charges
- How To Find The Best Resonance Structure By Applying Electronegativity
- Evaluating Resonance Structures With Negative Charges
- Evaluating Resonance Structures With Positive Charge
- Exploring Resonance: Pi-Donation
- Exploring Resonance: Pi-acceptors
- In Summary: Evaluating Resonance Structures
- Drawing Resonance Structures: 3 Common Mistakes To Avoid
- How to apply electronegativity and resonance to understand reactivity
- Bond Hybridization Practice
- Structure and Bonding Practice Quizzes
- Resonance Structures Practice
02 Acid Base Reactions
- Introduction to Acid-Base Reactions
- Acid Base Reactions In Organic Chemistry
- The Stronger The Acid, The Weaker The Conjugate Base
- Walkthrough of Acid-Base Reactions (3) - Acidity Trends
- Five Key Factors That Influence Acidity
- Acid-Base Reactions: Introducing Ka and pKa
- How to Use a pKa Table
- The pKa Table Is Your Friend
- A Handy Rule of Thumb for Acid-Base Reactions
- Acid Base Reactions Are Fast
- pKa Values Span 60 Orders Of Magnitude
- How Protonation and Deprotonation Affect Reactivity
- Acid Base Practice Problems
03 Alkanes and Nomenclature
- Meet the (Most Important) Functional Groups
- Condensed Formulas: Deciphering What the Brackets Mean
- Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions
- Don't Be Futyl, Learn The Butyls
- Primary, Secondary, Tertiary, Quaternary In Organic Chemistry
- Branching, and Its Affect On Melting and Boiling Points
- The Many, Many Ways of Drawing Butane
- Wedge And Dash Convention For Tetrahedral Carbon
- Common Mistakes in Organic Chemistry: Pentavalent Carbon
- Table of Functional Group Priorities for Nomenclature
- Summary Sheet - Alkane Nomenclature
- Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach
- Boiling Point Quizzes
- Organic Chemistry Nomenclature Quizzes
04 Conformations and Cycloalkanes
- Staggered vs Eclipsed Conformations of Ethane
- Conformational Isomers of Propane
- Newman Projection of Butane (and Gauche Conformation)
- Introduction to Cycloalkanes (1)
- Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes
- Calculation of Ring Strain In Cycloalkanes
- Cycloalkanes - Ring Strain In Cyclopropane And Cyclobutane
- Cyclohexane Conformations
- Cyclohexane Chair Conformation: An Aerial Tour
- How To Draw The Cyclohexane Chair Conformation
- The Cyclohexane Chair Flip
- The Cyclohexane Chair Flip - Energy Diagram
- Substituted Cyclohexanes - Axial vs Equatorial
- Ranking The Bulkiness Of Substituents On Cyclohexanes: "A-Values"
- The Ups and Downs of Cyclohexanes
- Cyclohexane Chair Conformation Stability: Which One Is Lower Energy?
- Fused Rings - Cis-Decalin and Trans-Decalin
- Naming Bicyclic Compounds - Fused, Bridged, and Spiro
- Bredt's Rule (And Summary of Cycloalkanes)
- Newman Projection Practice
- Cycloalkanes Practice Problems
05 A Primer On Organic Reactions
- The Most Important Question To Ask When Learning a New Reaction
- The 4 Major Classes of Reactions in Org 1
- Learning New Reactions: How Do The Electrons Move?
- How (and why) electrons flow
- The Third Most Important Question to Ask When Learning A New Reaction
- 7 Factors that stabilize negative charge in organic chemistry
- 7 Factors That Stabilize Positive Charge in Organic Chemistry
- Common Mistakes: Formal Charges Can Mislead
- Nucleophiles and Electrophiles
- Curved Arrows (for reactions)
- Curved Arrows (2): Initial Tails and Final Heads
- Nucleophilicity vs. Basicity
- The Three Classes of Nucleophiles
- What Makes A Good Nucleophile?
- What makes a good leaving group?
- 3 Factors That Stabilize Carbocations
- Equilibrium and Energy Relationships
- What's a Transition State?
- Hammond's Postulate
- Grossman's Rule
- Draw The Ugly Version First
- Learning Organic Chemistry Reactions: A Checklist (PDF)
- Introduction to Addition Reactions
- Introduction to Elimination Reactions
- Introduction to Free Radical Substitution Reactions
- Introduction to Oxidative Cleavage Reactions
06 Free Radical Reactions
- Bond Dissociation Energies = Homolytic Cleavage
- Free Radical Reactions
- 3 Factors That Stabilize Free Radicals
- What Factors Destabilize Free Radicals?
- Bond Strengths And Radical Stability
- Free Radical Initiation: Why Is "Light" Or "Heat" Required?
- Initiation, Propagation, Termination
- Monochlorination Products Of Propane, Pentane, And Other Alkanes
- Selectivity In Free Radical Reactions
- Selectivity in Free Radical Reactions: Bromination vs. Chlorination
- Halogenation At Tiffany's
- Allylic Bromination
- Bonus Topic: Allylic Rearrangements
- In Summary: Free Radicals
- Synthesis (2) - Reactions of Alkanes
- Free Radicals Practice Quizzes
07 Stereochemistry and Chirality
- Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers
- How To Draw The Enantiomer Of A Chiral Molecule
- How To Draw A Bond Rotation
- Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules
- Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) - The Method of Dots
- Enantiomers vs Diastereomers vs The Same? Two Methods For Solving Problems
- Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams)
- How To Determine R and S Configurations On A Fischer Projection
- The Meso Trap
- Optical Rotation, Optical Activity, and Specific Rotation
- Optical Purity and Enantiomeric Excess
- What's a Racemic Mixture?
- Chiral Allenes And Chiral Axes
- On Cats, Part 4: Enantiocats
- On Cats, Part 6: Stereocenters
- Stereochemistry Practice Problems and Quizzes
08 Substitution Reactions
- Introduction to Nucleophilic Substitution Reactions
- Walkthrough of Substitution Reactions (1) - Introduction
- Two Types of Nucleophilic Substitution Reactions
- The SN2 Mechanism
- Why the SN2 Reaction Is Powerful
- The SN1 Mechanism
- The Conjugate Acid Is A Better Leaving Group
- Comparing the SN1 and SN2 Reactions
- Polar Protic? Polar Aprotic? Nonpolar? All About Solvents
- Steric Hindrance is Like a Fat Goalie
- Common Blind Spot: Intramolecular Reactions
- The Conjugate Base is Always a Stronger Nucleophile
- Substitution Practice - SN1
- Substitution Practice - SN2
09 Elimination Reactions
- Elimination Reactions (1): Introduction And The Key Pattern
- Elimination Reactions (2): The Zaitsev Rule
- Elimination Reactions Are Favored By Heat
- Two Elimination Reaction Patterns
- The E1 Reaction
- The E2 Mechanism
- E1 vs E2: Comparing the E1 and E2 Reactions
- Antiperiplanar Relationships: The E2 Reaction and Cyclohexane Rings
- Bulky Bases in Elimination Reactions
- Comparing the E1 vs SN1 Reactions
- Elimination (E1) Reactions With Rearrangements
- E1cB - Elimination (Unimolecular) Conjugate Base
- Elimination (E1) Practice Problems And Solutions
- Elimination (E2) Practice Problems and Solutions
11 SN1/SN2/E1/E2 Decision
- Identifying Where Substitution and Elimination Reactions Happen
- Deciding SN1/SN2/E1/E2 (1) - The Substrate
- Deciding SN1/SN2/E1/E2 (2) - The Nucleophile/Base
- SN1 vs E1 and SN2 vs E2 : The Temperature
- Deciding SN1/SN2/E1/E2 - The Solvent
- Wrapup: The Quick N' Dirty Guide To SN1/SN2/E1/E2
- Alkyl Halide Reaction Map And Summary
- SN1 SN2 E1 E2 Practice Problems
12 Alkene Reactions
- E and Z Notation For Alkenes (+ Cis/Trans)
- Alkene Stability
- Addition Reactions: Elimination's Opposite
- Selective vs. Specific
- Regioselectivity In Alkene Addition Reactions
- Stereoselectivity In Alkene Addition Reactions: Syn vs Anti Addition
- Hydrohalogenation of Alkenes and Markovnikov's Rule
- Hydration of Alkenes With Aqueous Acid
- Rearrangements in Alkene Addition Reactions
- Addition Pattern #1: The "Carbocation Pathway"
- Halogenation of Alkenes and Halohydrin Formation
- Oxymercuration Demercuration of Alkenes
- Alkene Addition Pattern #2: The "Three-Membered Ring" Pathway
- Hydroboration Oxidation of Alkenes
- m-CPBA (meta-chloroperoxybenzoic acid)
- OsO4 (Osmium Tetroxide) for Dihydroxylation of Alkenes
- Palladium on Carbon (Pd/C) for Catalytic Hydrogenation
- Cyclopropanation of Alkenes
- Alkene Addition Pattern #3: The "Concerted" Pathway
- A Fourth Alkene Addition Pattern - Free Radical Addition
- Alkene Reactions: Ozonolysis
- Summary: Three Key Families Of Alkene Reaction Mechanisms
- Synthesis (4) - Alkene Reaction Map, Including Alkyl Halide Reactions
- Alkene Reactions Practice Problems
13 Alkyne Reactions
- Acetylides from Alkynes, And Substitution Reactions of Acetylides
- Partial Reduction of Alkynes With Lindlar's Catalyst or Na/NH3 To Obtain Cis or Trans Alkenes
- Hydroboration and Oxymercuration of Alkynes
- Alkyne Reaction Patterns - Hydrohalogenation - Carbocation Pathway
- Alkyne Halogenation: Bromination, Chlorination, and Iodination of Alkynes
- Alkyne Reactions - The "Concerted" Pathway
- Alkenes To Alkynes Via Halogenation And Elimination Reactions
- Alkynes Are A Blank Canvas
- Synthesis (5) - Reactions of Alkynes
- Alkyne Reactions Practice Problems With Answers
14 Alcohols, Epoxides and Ethers
- Alcohols - Nomenclature and Properties
- Alcohols Can Act As Acids Or Bases (And Why It Matters)
- Alcohols - Acidity and Basicity
- The Williamson Ether Synthesis
- Ethers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration
- Alcohols To Ethers via Acid Catalysis
- Cleavage Of Ethers With Acid
- Epoxides - The Outlier Of The Ether Family
- Opening of Epoxides With Acid
- Epoxide Ring Opening With Base
- Making Alkyl Halides From Alcohols
- Tosylates And Mesylates
- PBr3 and SOCl2
- Elimination Reactions of Alcohols
- Elimination of Alcohols To Alkenes With POCl3
- Alcohol Oxidation: "Strong" and "Weak" Oxidants
- Demystifying The Mechanisms of Alcohol Oxidations
- Protecting Groups For Alcohols
- Thiols And Thioethers
- Calculating the oxidation state of a carbon
- Oxidation and Reduction in Organic Chemistry
- Oxidation Ladders
- SOCl2 Mechanism For Alcohols To Alkyl Halides: SN2 versus SNi
- Alcohol Reactions Roadmap (PDF)
- Alcohol Reaction Practice Problems
- Epoxide Reaction Quizzes
- Oxidation and Reduction Practice Quizzes
- What's An Organometallic?
- Formation of Grignard and Organolithium Reagents
- Organometallics Are Strong Bases
- Reactions of Grignard Reagents
- Protecting Groups In Grignard Reactions
- Synthesis Problems Involving Grignard Reagents
- Grignard Reactions And Synthesis (2)
- Organocuprates (Gilman Reagents): How They're Made
- Gilman Reagents (Organocuprates): What They're Used For
- The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don't Belong In Most Introductory Organic Chemistry Courses)
- Reaction Map: Reactions of Organometallics
- Grignard Practice Problems
- Degrees of Unsaturation (or IHD, Index of Hydrogen Deficiency)
- Conjugation And Color (+ How Bleach Works)
- Introduction To UV-Vis Spectroscopy
- UV-Vis Spectroscopy: Absorbance of Carbonyls
- UV-Vis Spectroscopy: Practice Questions
- Bond Vibrations, Infrared Spectroscopy, and the "Ball and Spring" Model
- Infrared Spectroscopy: A Quick Primer On Interpreting Spectra
- IR Spectroscopy: 4 Practice Problems
- 1H NMR: How Many Signals?
- Homotopic, Enantiotopic, Diastereotopic
- Diastereotopic Protons in 1H NMR Spectroscopy: Examples
- C13 NMR - How Many Signals
- Liquid Gold: Pheromones In Doe Urine
- Natural Product Isolation (1) - Extraction
- Natural Product Isolation (2) - Purification Techniques, An Overview
- Structure Determination Case Study: Deer Tarsal Gland Pheromone
17 Dienes and MO Theory
- What To Expect In Organic Chemistry 2
- Are these molecules conjugated?
- Conjugation And Resonance In Organic Chemistry
- Bonding And Antibonding Pi Orbitals
- Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion
- Pi Molecular Orbitals of Butadiene
- Reactions of Dienes: 1,2 and 1,4 Addition
- Thermodynamic and Kinetic Products
- More On 1,2 and 1,4 Additions To Dienes
- s-cis and s-trans
- The Diels-Alder Reaction
- Cyclic Dienes and Dienophiles in the Diels-Alder Reaction
- Stereochemistry of the Diels-Alder Reaction
- Exo vs Endo Products In The Diels Alder: How To Tell Them Apart
- HOMO and LUMO In the Diels Alder Reaction
- Why Are Endo vs Exo Products Favored in the Diels-Alder Reaction?
- Diels-Alder Reaction: Kinetic and Thermodynamic Control
- The Retro Diels-Alder Reaction
- The Intramolecular Diels Alder Reaction
- Regiochemistry In The Diels-Alder Reaction
- The Cope and Claisen Rearrangements
- Electrocyclic Reactions
- Electrocyclic Ring Opening And Closure (2) - Six (or Eight) Pi Electrons
- Diels Alder Practice Problems
- Molecular Orbital Theory Practice
- Introduction To Aromaticity
- Rules For Aromaticity
- Huckel's Rule: What Does 4n+2 Mean?
- Aromatic, Non-Aromatic, or Antiaromatic? Some Practice Problems
- Antiaromatic Compounds and Antiaromaticity
- The Pi Molecular Orbitals of Benzene
- The Pi Molecular Orbitals of Cyclobutadiene
- Frost Circles
- Aromaticity Practice Quizzes
19 Reactions of Aromatic Molecules
- Electrophilic Aromatic Substitution: Introduction
- Activating and Deactivating Groups In Electrophilic Aromatic Substitution
- Electrophilic Aromatic Substitution - The Mechanism
- Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution
- Understanding Ortho, Para, and Meta Directors
- Why are halogens ortho- para- directors?
- Disubstituted Benzenes: The Strongest Electron-Donor "Wins"
- Electrophilic Aromatic Substitutions (1) - Halogenation of Benzene
- Electrophilic Aromatic Substitutions (2) - Nitration and Sulfonation
- EAS Reactions (3) - Friedel-Crafts Acylation and Friedel-Crafts Alkylation
- Intramolecular Friedel-Crafts Reactions
- Nucleophilic Aromatic Substitution (NAS)
- Nucleophilic Aromatic Substitution (2) - The Benzyne Mechanism
- Reactions on the "Benzylic" Carbon: Bromination And Oxidation
- The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions
- More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger
- Aromatic Synthesis (1) - "Order Of Operations"
- Synthesis of Benzene Derivatives (2) - Polarity Reversal
- Aromatic Synthesis (3) - Sulfonyl Blocking Groups
- Birch Reduction
- Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds
- Aromatic Reactions and Synthesis Practice
- Electrophilic Aromatic Substitution Practice Problems
20 Aldehydes and Ketones
- What's The Alpha Carbon In Carbonyl Compounds?
- Nucleophilic Addition To Carbonyls
- Aldehydes and Ketones: 14 Reactions With The Same Mechanism
- Sodium Borohydride (NaBH4) Reduction of Aldehydes and Ketones
- Grignard Reagents For Addition To Aldehydes and Ketones
- Wittig Reaction
- Hydrates, Hemiacetals, and Acetals
- Imines - Properties, Formation, Reactions, and Mechanisms
- All About Enamines
- Breaking Down Carbonyl Reaction Mechanisms: Reactions of Anionic Nucleophiles (Part 2)
- Aldehydes Ketones Reaction Practice
21 Carboxylic Acid Derivatives
- Nucleophilic Acyl Substitution (With Negatively Charged Nucleophiles)
- Addition-Elimination Mechanisms With Neutral Nucleophiles (Including Acid Catalysis)
- Basic Hydrolysis of Esters - Saponification
- Proton Transfer
- Fischer Esterification - Carboxylic Acid to Ester Under Acidic Conditions
- Lithium Aluminum Hydride (LiAlH4) For Reduction of Carboxylic Acid Derivatives
- LiAlH[Ot-Bu]3 For The Reduction of Acid Halides To Aldehydes
- Di-isobutyl Aluminum Hydride (DIBAL) For The Partial Reduction of Esters and Nitriles
- Amide Hydrolysis
- Thionyl Chloride (SOCl2)
- Diazomethane (CH2N2)
- Carbonyl Chemistry: Learn Six Mechanisms For the Price Of One
- Making Music With Mechanisms (PADPED)
- Carboxylic Acid Derivatives Practice Questions
22 Enols and Enolates
- Keto-Enol Tautomerism
- Enolates - Formation, Stability, and Simple Reactions
- Kinetic Versus Thermodynamic Enolates
- Aldol Addition and Condensation Reactions
- Reactions of Enols - Acid-Catalyzed Aldol, Halogenation, and Mannich Reactions
- Claisen Condensation and Dieckmann Condensation
- The Malonic Ester and Acetoacetic Ester Synthesis
- The Michael Addition Reaction and Conjugate Addition
- The Robinson Annulation
- Haloform Reaction
- The Hell–Volhard–Zelinsky Reaction
- Enols and Enolates Practice Quizzes
- The Amide Functional Group: Properties, Synthesis, and Nomenclature
- Basicity of Amines And pKaH
- 5 Key Basicity Trends of Amines
- The Mesomeric Effect And Aromatic Amines
- Nucleophilicity of Amines
- Alkylation of Amines (Sucks!)
- Reductive Amination
- The Gabriel Synthesis
- Some Reactions of Azides
- The Hofmann Elimination
- The Hofmann and Curtius Rearrangements
- The Cope Elimination
- Protecting Groups for Amines - Carbamates
- The Strecker Synthesis of Amino Acids
- Introduction to Peptide Synthesis
- Reactions of Diazonium Salts: Sandmeyer and Related Reactions
- Amine Practice Questions
- D and L Notation For Sugars
- Pyranoses and Furanoses: Ring-Chain Tautomerism In Sugars
- What is Mutarotation?
- Reducing Sugars
- The Big Damn Post Of Carbohydrate-Related Chemistry Definitions
- The Haworth Projection
- Converting a Fischer Projection To A Haworth (And Vice Versa)
- Reactions of Sugars: Glycosylation and Protection
- The Ruff Degradation and Kiliani-Fischer Synthesis
- Isoelectric Points of Amino Acids (and How To Calculate Them)
- Carbohydrates Practice
- Amino Acid Quizzes
25 Fun and Miscellaneous
- Organic Chemistry GIFS - Resonance Forms
- Organic Chemistry and the New MCAT
- A Gallery of Some Interesting Molecules From Nature
- The Organic Chemistry Behind "The Pill"
- Maybe they should call them, "Formal Wins" ?
- Intramolecular Reactions of Alcohols and Ethers
- Planning Organic Synthesis With "Reaction Maps"
- Organic Chemistry Is Shit
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