The following video series is a review of Organic Chemistry I.
The videos average 8-10 minutes each and were created by ALTC peer educators Arielle Morris and Sydney Koehne.
Episode 1: Bonding Orbitals
Everything you need to know about orbitals (and dipoles) to do well in organic chem: molecular orbital theory, hybridization, and net dipole moments. Important vocabulary terms such as HOMO, LUMO, LCAO, etc. are explained, as well as other important considerations regarding electrons, bonding, and vector addition.
Episode 2: Resonance Patterns, Rules, Formal Charges, and Examples
Everything important to know about resonance: First 6:30 is conceptual importance of resonance, including the 5 main resonance patterns, delocalized vs. localized lone pairs, a common resonance mistake, and significance of Formal Charges in resonance significance/stability. The last 7:24 minutes of the video give 2 examples, one delocalizing a negative charge and one delocalizing a positive charge, and show how to rank resonance structures in terms of stability and significance.
Episode 3: Acid-Based Chemistry
pKa, ARIO, examples, and definitions: everything you need to know about acids and bases to do well in organic chemistry II.
Episode 4: Naming Alkanes, Cycloalkanes, and Bicycylic Compounds
In this video, I discuss prefixes for naming parents and substituents, how to name and identify complex substituents, the steps for naming for alkanes/cycloalkanes, tie brakes/important rules, and steps naming bicyclic compounds in the first 6:30 of the video, all in that order. The rest of the video consists of 3 naming practice problems explained.
Episode 5.1: Newman Projections
In this video, I go over some tricks to drawing Newman projections, up until 2:38, and the rest of the video consists of a practice problem for drawing Newman projections.
Episode 5.2: Rotations, Conformational Analysis, and Newman Projections
In this video, I go over rotating Newman Projections (0:10-1:45), and then I get into a practice problem for the rest of the video. Steps 1-3 Involve rotating the initial Newman projection in 60-degree increments, clockwise, and then labeling the forms as eclipsed or staggered. Step 4 then ranks the energy of the conformers. Make sure to click through the video if you find any of the steps particularly confusing and would like to focus on that step!
Episode 6.1: Chirality, Stereoisomers, Enantiomers, and Diastereomers
The first 3 minutes of this video discuss chirality, constitutional isomers, stereoisomers, enantiomers, and diastereomers, as a general overview. Then, from about 3:15 to 5, I discuss enantiomers and give examples in many different forms. The rest of this video discusses diastereomers and gives examples in many different forms.
Episode 6.2: R-S Chiral Centers, E-Z Alkenes, Meso Compounds, Optical Activity
This video discusses R & S configurations of chiral centers (0:15-2:15), gives an example problem for R & S configurations (2:15-4:10), E & Z alkenes (4:15-5:20), a practice problem with E and Z alkenes (5:20-7:05), Meso Compounds and Optical Activity (7:05-8:10), and a practice problem with Meso Compounds and Optical Activity (8:15-end)
Episode 7.1: Conformations of Cyclohexane- Chair Conformations
Conformations of Cyclohexanes & Chair Conformations: First 5:20 discusses how to draw chair conformations, rest of the video is a practice problem for going from a cyclohexane to a chair conformation, and analyzing which of the 2 conformations is more stable or favorable at room temperature.
Episode 7.2: Cis-Trans Stereoisomers and Bicyclic Chair Conformations
This video discusses cis and trans stereoisomers, specifically cis-decalin and trans-decalin as examples, from 0:15-1:30. Then, the video goes into a practice problem for drawing the bicyclic chair conformations for cis-decalin and trans-decalin, in that order, and then determining which conformation of the stereisomers is more stable after that.
Episode 8: Fischer Projections
Fischer Projections: the basics, determining R and S configuration of Fischer projections (example for most of the video with steps), as well as Fischer projection isomers: enantiomers and diastereomers.
Episode 9: Introduction to Rxns- Mechanisms
The essentials from all of chapter 6 compiled into one video. Basic intro to kinetics, energy diagrams, nucleophiles, electrophiles, and carbocations. This video only gives the highlights, but serves as a stepping stone into the world of reaction mechanisms! (PS if you don't need the full video, I divided it into segments in the same order listed previously, so just skip to the part you need!)
Episode 10.1: Conceptual SN2, E2, SN1, E1
Everything you need to know about the conceptual information pertaining to SN2, E2, SN1, and E1 reactions (preparation for practice problems). The first 2 minutes discusses a quick intro and solvents. From about 2 to 8 minutes, I go over the substrates and reactants. Finally, from 8 minutes to the end, I discuss regioselectivity, stereoselectivity, and stereospecificity. For practice problems that will be around the level of difficulty of the exam pertaining to SN2, E2, SN1, and E1, please go to pages 335 to 341 (problems 7.47-7.106) of the textbook, and for the solutions to those problems, those can be found in the solution manual from pages 208 to 233.
Episode 11: Hydrohalogenation
Learn the difference between Markovnikov and anti-Markovnikov addition of hydrogen and a halide across a double bond. We discuss the reagents and mechanisms for both methods of addition. Carbocation rearrangements are introduced in-depth.
Episode 12: Hydration
Acid-catalyzed hydration and oxymercuration-demercuration are two reactions that add water across a double bond in a Markovnikov addition. Mechanisms, stereochemistry, and rearrangements are the focus of this video!
Episode 13: Hydroboration- Oxidation
An in-depth discussion of the mechanism for hydroboration-oxidation that explains all the key features of the reaction and its products!
Episode 14: Hydrogenation
Featured is a brief discussion of catalytic hydrogenation, as well as a synopsis of the mechanism that highlights the regio- and stereochemical outcomes specific to this reaction.
Episode 15: Halogenation- Halohydrin Formation
Learn about halogenation and halohydrin formation through a detailed comparison of their mechanisms and regioselectivity!
Episode 16: Dihydroxylation
Discussion of both syn and anti dihydroxylation, from reagents to mechanisms to key concepts such as epoxide formation.
Episode 17: Ozonolysis
An overview of the ozonolysis reaction and some example problems!
Episode 18: Prep of Alkynes
How to prepare terminal alkynes using elimination. Includes a brief overview of acidity, equilibria, and our selection of base.
Episode 19: Reduction of Alkynes
Using alkynes to make alkenes and alkanes in two ways: catalytic hydrogenation and dissolving metal reduction. Featured is a discussion of the dissolving metal reduction mechanism as well as a comparison of the two reduction methods.
Episode 20: Hydrohalogenation of Alkynes
Hydrohalogenation of alkynes is very similar to the process for alkenes, so this is just a quick video that points out the differences between the two reactions.
Episode 21: Hydration of Alkynes
Acid-catalyzed hydration and hydroboration oxidation are compared in this video and represent the markovnikov and anti-markovnikov addition of water across a triple bond, respectively. This video mainly focuses on mechanistic considerations and on the idea of keto-enol tautomerization, which is defined and discussed at length. These hydration reactions are essential to second-semester organic chemistry, so follow along to learn how to synthesize two very important molecules: ketones and aldehydes!
Episode 22: Halogenation- Alkylation of Alkynes
Brief overview of halogenation and ozonolysis of alkynes. Both reactions as well as examples are explained.
Episode 23: Alkylation of Terminal Alkynes
Tips, tricks, and examples for understanding the alkylation of terminal alkynes. This reaction is very useful for synthesis problems, so be sure to keep this one in mind!
Episode 24: Radical Reactions and Mechanisms
Learn about the 3 most important/synthetically useful radical reactions! I'll walk you through a basic tutorial of radical mechanisms and explain how kinetics, thermodynamics, and resonance come into play with our 3 main radical reactions.
Episode 25: Synthesis Strategies
Strategies for tackling synthesis problems on exams: learn patterns, tips, and tricks that will help you be successful in organic chemistry!
Episode 26: Preparation of Alcohols_Diols
In this video, we go over how to prepare both alcohols and diols using both new and familiar methods. Get a quick overview of previous reactions and also learn how to prepare alcohols and diols using the reduction of carbonyls! Reduction is a very useful and super simple synthetic technique. For help understanding oxidation/reduction, please see the gen chem videos for a refresher.
Episode 27: Grignards
Grignards are very useful in synthesis, so learn all about Grignard reagents in this video! We'll go over the types of reactants that a Grignard can be used on, the reaction mechanisms, and also two exceptions to Grignards' usefulness.
Episode 28: Protecting Alcohols
A brief discussion on how and why to protect alcohols, which is a skill you'll need for second-semester organic chem!
Episode 29: Reactions of Alcohols
Let's talk about all the reactions that alcohols can go through: substitution, elimination, and oxidation. Since we already know how to do substitution and elimination, oxidation is the main focus of this video.
