SST_ITOUC_ROCIOThe following videos serve as aids for more effective class preparation when you read the chapter material and work the assigned problems before each class.

  • Complex Amine Synthesis (M4V)
    This video illustrates one example or a reasonably complicated, multi-step synthesis of an amine from an alkyl bromide, involving a variety of synthetic steps to reach the target molecule.
  • Hoffman Elimination (M4V)
    This reaction involves the traditional elimination mechanism, after initial conversion of the amine into an ammonium leaving group. This reaction was discovered by Dustin Hoffman, who was a chemist before he became a well-known actor.
  • Reductive Amination (M4V)
    Addition of an amine (or ammonia) to an aldehyde or ketone, followed by reduction with sodium borohydride; this video details this synthetic scheme.
  • Ways to make Amines (M4V)
    This video illustrates various synthetic schemes that can be used to prepare amines, through the use of several example syntheses.
  • Naming Amines (M4V)
    This video provides the rules for naming amines, and illustrates these rules through the use of several example molecules. This video includes naming conventions for aliphatic, aromatic and heterocylic amines (the last of these tend to have common, rather than IUPAC, names).
  • Micheal Reaction (M4V)
    This video illustrates the mechanism involved when an enolate reacts with an α,β?unsaturated carbonyl compound.
  • Dieckmann Reaction (M4V)
    Just as Aldol reactions can occur in an intramolecular fashion, so can the Claisen condensation. This video illustrates the mechanism of this reaction, known as the Dieckmann reaction.
  • Claisen Condensation (M4V)
    A variant of the Aldol condensation, except where the starting materials are two esters rather than aldehydes or ketones. This video illustrates the mechanism of the Claisen condensation.
  • Aldol Reaction (M4V)
    Arguably the most important example of an enolate addition reaction; this video illustrates the mechanism of the aldol reaction between two carbonyl compounds (aldehydes or ketones).
  • Aldol Condensation (M4V)
    The aldol reaction can also go one step further and produce a condensation product, via elimination of water. The mechanism of this reaction is covered in this video ? because the aldol reaction product is a precursor to this reaction, this is also covered.
  • Intra Molecular Aldol Reaction (M4V)
    The aldol reaction also occurs when two carbonyl groups are present within the same molecule; this video illustrates the mechanism of this reaction, along with its corresponding condensation.
  • Acetoacetic Ester Synthesis (M4V)
    This video illustrates the mechanism of the acetoacetic ester synthesis, in which ethyl acetoacetate is used to convert an alkyl halide into a methyl ketone with at least three extra carbon atoms.
  • Malonic Ester Synthesis (M4V)
    This video illustrates the mechanism of the malonic ester synthesis, in which diethyl malonate is used to convert an alkyl halide into a carboxylic acid with at least two extra carbon atoms.
  • Direct Alkylation (M4V)
    One of the most common reaction types of enolates, alkylation at the α-carbon, is discussed in this video, using examples of enolates formed from different functional groups.
  • Alpha Hydrogens (M4V)
    Understanding enolate chemistry requires knowledge of what hydrogens are and how to recognize them in a molecule; this video illustrates then concept through a set of sample structures.
  • Alpha Halogenation (M4V)
    This video illustrates the halogenation of an aldehyde or a ketone at the α?carbon (hence the name α?halogenation), via an enolate intermediate reacting with bromine.
  • Keto Enol Tautomerism (M4V)
    This video details both the acid- and base-catalyzed tautomerization mechanisms between keto and enol forms of carbonyl compounds.
  • Polymers (M4V)
    Details structures of the various types of step-growth polymers available, and the materials they are made from, as well as some common uses.
  • Nucleophilic Acyl Substitutions (M4V)
    This video illustrates one type of reaction that is specific to carboxylic acid derivatives ? these are carbonyl compounds that undergo substitutions, rather than additions, at the carbonyl carbon. Several examples are used to provide clarification.
  • Fisher Esterification (M4V)
    Details the mechanism of one of the most common methods of ester preparation, from the acid-catalyzed reaction of an alcohol and a carboxylic acid.
  • Fisher Projection Basics (M4V)
    Fisher Projections are arguably the 3-D structure representations that cause students the most headaches. This video illustrates, through the use of several simple examples cases, that what Fisher projections are showing is much simpler than many students think. They are not that complicated.
  • Fisher Projection for Sugars (M4V)
    This video illustrates that, with an understanding of Fisher projection basics, expanding those concepts to larger molecules such as sugars is quite easily achievable. Several examples are included in the video to help clarify the concepts.
  • Reactivity of Acid Derivatives (M4V)
    The different carboxylic acid derivatives all have varying reactivities, and this video compares these differences, and relates them to leaving group ability in each derivative.
  • Naming Acid Derivatives (M4V)
    This video provides the rules for naming carboxylic acid derivatives such as acid chlorides, esters, amides, and anhydrides, and illustrates these rules through the use of several example molecules
  • Acidic Hydrolysis of Nitriles (M4V)
    Outlines the long mechanism of acidic hydrolysis of nitriles - first to amides and then to carboxylic acids. As always, an understanding of electron-pushing fundamentals will make this particularly lengthy mechanism more palatable.
  • Carboxylic Acid Synthesis (M4V)
    This video details various synthetic methods to form the carboxylic acid functional group, along with some example syntheses.
  • Wittig Reaction (M4V)
    This video illustrates the reaction and mechanism of one of the most important synthetic methods to form alkenes. Example syntheses are used to help clarify the concepts involved.
  • Imine Enamine Formation (M4V)
    Details the reaction mechanism that accounts for the formation of imines/enamines when aldehydes and ketones react with 1o / 2o amines, respectively. Although it's a lengthy mechanism, an understanding of basic electron-pushing principles makes it much easier to follow.
  • Acetal Formation (M4V)
    Details the reaction mechanism that accounts for the formation of acetals when alcohols react with aldehydes and/or ketones. Although it's a lengthy mechanism, an understanding of basic electron-pushing principles makes it much easier to follow.
  • Grignard Reactions (M4V)
    Arguably the most important reaction in organic synthesis, the Grignard reaction and how it works is detailed in this video; several examples of its use are also included.
  • Grignard Reactions in Organic Chemistry (M4V)
    Due to its importance in organic synthesis, this video details some basics about why the Grignard reaction is so useful, and how it can be used in a synthetic reaction scheme (C-C bond formation).
  • Hydride Reductions (M4V)
    Hydride reductions are one of the nucleophilic addition reactions that dominate the chemistry of aldehydes and ketones. This video explains this reaction, as well as its similarity to the other nucleophilic addition reactions.
  • Naming Aldehydes and Ketones (M4V)
    This video provides the rules for naming aldehydes and ketones, and illustrates these rules through the use of several example molecules.
  • Naming Ethers and Sulphides (M4V)
    This video provides the rules for naming ethers and sulfides, and illustrates these rules through the use of several example molecules.
  • Williamson Ether Synthesis (M4V)
    The most important reaction for preparing ethers is explained in this video, along with several examples; it's a particularly useful reaction in organic synthesis.
  • Reactions of Ethers (M4V)
    Explains the main reaction that ethers undergo cleavage into two separate molecules when reacted with a strong acid. The video also illustrates that ether structure is key in determining where in the molecule the ether cleavage occurs.
  • Naming Alcohols (M4V)
    This video provides the rules for naming alcohols, and illustrates these rules through the use of several example molecules.
  • Directing in EAS Reactions (M4V)
    Details how different substituents on a benzene ring direct where a new group is introduced in an EAS reaction. The different categories of substituents are discussed, and the concepts are illustrated through the use of several examples.
  • EAS Reactions (M4V)
    This video details various synthetic methods to form the carboxylic acid functional group, along with some example syntheses.
  • Naming Aromatics (M4V)
    This video provides the rules for naming mono-, di- and poly-substituted benzene derivatives, and illustrates these rules through the use of several example molecules.
  • Addition to Conjugated Dienes (M4V)
    Addition of HBr to conjugated dienes results in more products than at first expected; the extra products formed from resonance stabilization of the carbocation intermediate are explained here, as is the mechanism of the reaction.