Kinetic Versus Thermodynamic Enolates
Kinetic versus Thermodynamic Enolates of Ketones Enolates have a lot in common with alkenes. They are flat and have a C-C pi bond. Zaitsev’s rule
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The Hofmann Elimination
The Hofmann Elimination Of Alkylammonium Salts: Examples and Mechanism The Hofmann Elimination is an elimination reaction of alkylammonium salts that forms C-C double bonds [pi
Read moreBulky Bases in Elimination Reactions
Elimination Reactions Using “Bulky Bases” – When The Zaitsev Product Is Minor We’ve recently talked about Zaitsev’s rule in elimination reactions, and how the transition
Read moreComparing the SN1 and SN2 Reactions
Comparing the SN1 and SN2 Reactions In nucleophilic substitution reactions, a bond between carbon and a leaving group (C–LG) is broken, and a new bond
Read moreWhat Makes A Good Nucleophile?
Factors That Determine Whether A Species Is A Good Nucleophile If you read the last post, you’ll recall that a nucleophile is a species that
Read moreReagent Friday: Potassium tert-butoxide [KOC(CH3)3]
Potassium tert-Butoxide (KOt-Bu) Is A Bulky Base In a blatant plug for the Reagent Guide and the Reagents App for iPhone, each Friday I profile a different reagent that
Read moreDi-isobutyl Aluminum Hydride (DIBAL) For The Partial Reduction of Esters and Nitriles
DIBAL (Di-isobutyl Aluminum Hydride) – A Bulky Reducing Agent For The Partial Reduction Of Esters and Nitriles DIBAL (also known as DIBAL-H or DIBAH) is
Read moreReagent Friday: Lithium Di-isopropyl Amide (LDA)
Lithium Diisopropyl Amide (LDA), A Strong, Sterically Hindered Base In a blatant plug for the Reagent Guide, each Friday I profile a different reagent that is
Read moreSteric Hindrance is Like a Fat Goalie
Steric Hindrance In Nucleophilic Substitution Reactions Sportswriter Todd Gallagher asked a question that every hockey fan has probably asked at one point. “Could a morbidly
Read moreThe Ups and Downs of Cyclohexanes
Drawing cyclohexane chair forms can be a tricky business. While it’s often intuitive to pick out which groups are up and down when they’re axial
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