Reagent Friday: Potassium tert-butoxide [KOC(CH3)3]
…commonly encountered in Org 1/ Org 2. Sometime back in general chemistry you (hopefully) learned that hydroxide ion (HO-) is a strong base. It’s the conjugate base of water –…
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A Fourth Alkene Addition Pattern – Free Radical Addition
…result in a new free radical on a secondary carbon. Attack of the bromine radical on the less substituted carbon would result in a new free radical on a tertiary…
Read moreWhat Makes A Good Nucleophile?
…to form a new covalent bond. Nucleophilicity is measured by comparing reaction rates; the faster the reaction, the better (or, “stronger”) the nucleophile. Table of Contents Reminder: Nucleophilicity Is Measured…
Read moreLiAlH[Ot-Bu]3 For The Reduction of Acid Halides To Aldehydes
…of LiAlH4 such that only the most reactive C=O bonds are reduced. One example is the reagent formed when LiAlH4 is treated with three equivalents of t-butanol to give lithium…
Read moreIntramolecular Reactions of Alcohols and Ethers
…up a tremendous amount on exams. Think of instructors as a bit like baseball pitchers. When it comes to exams, they don’t always groove fastballs down the centre of the…
Read moreEvaluating Resonance Structures With Positive Charge
…new π bond that has been formed through the donation of a pair of electrons on the adjacent atom (O, N, Cl, F). In the process we put a positive…
Read moreLithium Aluminum Hydride (LiAlH4) For Reduction of Carboxylic Acid Derivatives
…also reduce nitriles and amides to amines Finally it can open epoxides as well as reduce alkyl halides to alkanes. Table of Contents Lithium Aluminum Hydride, LiAlH4 LiAlH4 vs NaBH4…
Read moreMaybe they should call them, “Formal Wins” ?
…modern computational techniques, we can calculate charge densities extremely well. From these calculations, it’s easy to see where charge is distributed throughout the molecule. For example, ClO- below; oxygen is…
Read moreEvaluating Resonance Forms (1) – The Rule of Least Charges
…to get different resonance forms. Every resonance form we can draw for a molecule can be made through a combination of these three moves. We can apply these “moves”…
Read moreIntroduction to Resonance
…mention a second key factor that can complicate the analysis of electron densities: the presence of double bonds (π bonds). In this post we will see how combining an understanding…
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