Acid Catalyzed Hydration of Alkenes Reaction and Mechanism

Acid catalyzed hydration of alkenes involves replacing the pi bond on an alkene with a water molecule.  This is done by adding an alcohol to the more substituted carbon atom, and hydrogen to the less substituted carbon atom. This reaction follows Markovnikov’s rule and may undergo a carbocation rearrangement. If it is chiral, the product […]

Backpack Trick for Organic Chemistry Reactions

When it comes to organic chemistry reactions, many students focus on learning the EXACT steps by memorizing the SPECIFIC molecules presented in their books and lecture slides. Then, when something looks even slightly different on the exam, they panic! One such scenario: replacing water with alcohol in a reaction sequence – either as the attacking molecule or […]

Markovnikov vs Anti-Markovnikov in Alkene Addition Reactions

Markovnikov’s Rule tells us where to add the nucleophile and hydrogen in an asymmetrical alkene addition reaction. This is a critical pattern to both understand and recognize when studying alkene addition reactions. What is Markovnikov’s rule all about and how does this impact regioselectivity in electrophilic addition reactions? As you follow along with my alkene reactions […]

Hydroboration Oxidation of Alkenes

Hydroboration-oxidation is yet another alcohol yielding alkene reaction. However this reaction results in an alcohol adding to the less substituted carbon for an anti-Markovnikov product. The video below helps you understand the reactivity of Boron as well as the hydroboration and oxidation steps of the reaction mechanism. Watch this video on YouTube or read the […]

Alkoxymercuration Demercuration Reduction of Alkenes

Alkoxymercuration-Demercuration Reduction is a tricky mechanism for organic chemistry students. Not because it’s any more difficult than oxymercuration, but simply because students tend to overlook the alcohol reagent and miss the alkyl group in the product. The video below helps you understand the similarities and differences between oxymercuration and alkoxymercuration of alkenes. The video also […]

Oxymercuration-Demercuration Alkene Reaction Mechanism

Oxymercuration-Demercuration, also referred to as oxymercuration-reduction is slightly more confusing than that average alkene reaction. I think it’s a combination of the extra steps, involvement of mercury, and the mysterious reduction by sodium borohydride. But don’t let this confuse you. The video below takes you through the entire reaction mechanism with step by step explanations […]