Organic Chemistry-related videos from YouTube

Most of these videos are from the MolModAc Project at the University of Illinois or the Royal Society of Chemistry.

Click on the pictures to watch the individual video; once the video page opens, right-click and press "full screen" to view a larger format.

Conjugation

Conjugated Systems; Chapter 10

Linear conjugation versus cross conjugation in extended pi systems; care needs to be taken when deciding the actual extent of conjugation in polyunsaturated molecules.

DielsAlder1

The Diels-Alder Reaction; Chapter 10

Introduction to the Diels-Alder reaction in terms of stereochemical outcome and inference in mechanism. Discussion of endo and exo transition states.

DielsAlder2

The Diels-Alder Reaction; Chapter 10

Further examples of Diels-Alder cycloaddition reactions and stereochemical outcomes. Additional discussion of endo and exo possibilities.

Aromaticity

Aromaticity; Chapter 11

An introduction to the requirements for aromaticity, Huckel's rule, and the diversity of aromatic and heteroaromatic compounds found in Organic Chemistry and Biochemistry.

Huckel

Aromaticity; Chapter 11

Criteria used for counting the electrons in both aromatic and non-aromatic pi systems, including carbon and heteroaromatic systems with lone pairs.

Frost

Aromaticity; Chapter 11

The Frost circle, a device for determining the populations of bonding, non-bonding, and antibonding orbitals in conjugated cyclic systems.

EAS1

Electronic Effects in EAS; Chapter 12

A discussion of the different effects that substituents on a benzene system have on the reactivity of the ring, as well as the effect on electron density at each carbon within the cycle.

EAS2

Directing Effects in EAS; Chapter 12

Substituent effects in Electrophilic Aromatic Substitution; how each type of group either stabilizes or destabilizes the intermediate cation and how that influences product distribution.

Heteroaromatics

Heteroaromatics: Chapter 12

The aromatic heterocycles pyridine and pyrrole are compared and charaterized as being electron-poor and electron-rich, respectively, based on the resonance possibilities within the cycles.

Heteroaromatics2

Heteroaromatic Reactivity; Chapter 12

A description of the reactivity of electron-poor and electron-rich heterocyles in the presence of electrophiles and nucleophiles; lone pair inclusion in the aromatic sextet being key.

Infrared

Introduction to Infra-Red Spectroscopy; Chapter 13

Infra-Red spectroscopy is discussed from the basics of bond vibration to the assembly of the IR spectrometer; examples of output (spectra) and interpretation are given.

NMR1

Nuclear Magnetic Resonance Spectroscopy; Chapter 13

A Flash-based exercise on how to determine the number and type of protons in an organic molecule. The examples should be studied in conjunction with the Spectroscopy Sheet.

NMR2

Nuclear Magnetic Resonance Spectroscopy; Chapter 13

A second Flash-based exercise in NMR spectroscopy in which proton spectra are matched to one of three possible molecules. Use the Spectroscopy Sheet to practice working with spectra.

NMR3

Nuclear Magnetic Resonance Spectroscopy; Chapter 13

The superconducting magnets required for modern NMR (Nuclear Magnetic Resonace) spectroscopy need to be cooled to liquid helium temperatures to work; usually a "quench" is very bad news.

MassSpec

Mass Spectrometry basics; Chapter 13

Mass spectrometry is a very sensitive technique used in Chemistry and Forensic Science to identify organic and biological molecules; the spectra reveal information about structure and isotope ratios.

Acidbase

Acid-base concepts; Chapter 14-20

A review of the important concepts that dictate the pKa of acids as they relate to organometallic stability and protonation of carbonyls in the upcoming chapters.

Anions

Carbanion stability; Chapter 14-20

Discussion of relative carbanion stability based on hybridization, resonance, and solvation effects; important for upcoming nucleophilic addition chemistry.

Aromaticity

Organometallic reagents and reactions; Chapter 14

Carbon nucleophiles (carbanions) may be generated by reacting alkyl and aryl halides with metals such as Mg or Li. The polarization in these reagents allows them to react as carbon nucleophiles.

Aromaticity

Nucleophilic Addition reactions; Chapter 14-15

General concepts of nucleophilic addition to polarized carbonyl groups in aldehydes and ketones. Use of C-nucleophiles for C-C bond formation and of hydride reagents in reduction processes.

Aromaticity

Esterification reactions; Chapter 15

Mechanisms of esterifications at differing pH. Use of acylation reagents (anhydrides, acyl chlorides) under basic conditions, as well as the Fischer esterification under acidic conditions. MolModAc Project, University of Illinois.

Aromaticity

Ring-opening of Epoxides; Chapter 16

Discussion of the different ring-opening reactions that epoxides undergo. Acid-catalyzed opening at the more highly-substituted carbon (SN1-control); base-promoted opening at the less-hindered carbon (SN2 control).

Aromaticity

Summary of Carbonyl Functional Groups; Chapters 17-20

A summary of the different classes of carbonyl compound encountered in the remaining chapters of the second semester. Classified generally as aldehydes/ketones and compounds with a heteroatom (potential leaving group) attached. Definition of alpha carbon. MolModAc Project, University of Illinois.

Aromaticity

Acetals and Ketals; Chapter 17

Reactions of aldehydes and ketones to produce acetals and ketals, respectively. Mechanism of acid-catalyzed formation using alcohols and acid and experimental details of synthesis. Stability and use as protecting groups, as well as hydrolysis back to carbonyl. MolModAc Project, University of Illinois.

Aromaticity

Formation of Imines; Chapter 17

Treatment of aldehydes and ketones to form imines and enamines. Nucleophilic addition of different amines followed by loss of water to produce C=N functional groups or elimination at the alpha C to give enamine species. MolModAc Project, University of Illinois.

Aromaticity

The Wittig reaction; Chapter 17

The use of phosphonium ylides in addition to alkenes is discussed. The formation of the stable R3P=O species allows for a carbonyl to be turned into an alkene. The Wittig reaction mechanism is discussed in detail. MolModAc Project, University of Illinois.

Aromaticity

Classes of Carbonyl Functional Groups; Chapters 17-20

Definitions of different carbonyl functional groups found in chemistry and biology. Overview of reactivity with nucleophiles and bases. Definition of alpha carbon and alpha,beta-unsaturated systems. MolModAc Project, University of Illinois.

acid derivatives

Carboxylic Acids and Derivatives; Chapters 18-19

Classification of carboxylic acids and their derivatives such as esters, acid chlorides, anhydrides, and amides. Interconversion of each class of compound through nucleophilic acyl substitution. Effect of leaving group and nucleophile strength. MolModAc Project, University of Illinois.

acid derivatives

Carboxylic Acids and Derivatives; Chapters 18-19

Reactivity of carboxylic acids and their derivatives. Nucleophilic acyl substitution mechanism to describe interconversion; discussion of leaving group ability as related to base and conjugate-acid strength. Reaction profiles to describe energetic changes. MolModAc Project, University of Illinois.

esterification

Carboxylic Acids and Derivatives; Chapters 18-19

Mechanisms of ester formation at different pH. Review of Fischer esterification process under acidic catalysis, and also of esterification in base using anhydrides and acid chlorides. MolModAc Project, University of Illinois.

alpha acidity

Enols and Enolates; Chapter 20

Discussion of the acidity of alpha protons in aldehydes, ketones, esters, etc. Effect of EWG on pKa and conjugate base strength. Relationship between enols and enolates and their use as nucleophiles in upcoming nucleophilic addition-type reactions. MolModAc Project, University of Illinois.

tautomers

Enols and Enolates; Chapter 20

Details of keto-enol tautomerism and the potential nucleophilicity of the alpha carbon. Similarity between enols and enamines (formed from aldehydes/ketones and secondary amines). Carbonyls with alpha H may therefore be sources of both electrophiles and nucleophiles. MolModAc Project, University of Illinois.

aldol

Enols and Enolates; Chapter 20

Details of keto-enol tautomerism and the potential nucleophilicity of the alpha carbon. Similarity between enols and enamines (formed from aldehydes/ketones and secondary amines). Carbonyls with alpha H may therefore be sources of both electrophiles and nucleophiles. MolModAc Project, University of Illinois.

aldol

Enols and Enolates; Chapter 20

Aldol reactions with two enolizable carbonyl starting materials. Equilibrium produces two nucleophiles and a mixture of products usually results. Reaction is made useful by employing one substrate that has an enolizable H and one that does not to limit mucleophilic species possible. MolModAc Project, University of Illinois.

aldol

Enols and Enolates; Chapter 20

Claisen condensations with two enolizable ester starting materials. Equilibrium produces two nucleophiles and a mixture of products usually results. Reaction is made useful by employing one substrate that has an enolizable H and one that does not to limit mucleophilic species present. MolModAc Project, University of Illinois.

aldol

Enols and Enolates; Chapter 20

Michael reaction using stabilized enolates from 1,3-dicarbonyl compounds. 1,2- versus 1,4-addition (kinetic versus thermodynamic processes). Formation of enol and subsequent tautomerism to reveal ketone product. MolModAc Project, University of Illinois.