Alkene Reaction Mechanisms in Organic Chemistry

organic chemistry alkene reaction mechanism tutorial videosAlkene reactions are the core foundation to learning reaction mechanisms in organic chemistry. These are likely the first set of reaction mechanisms covered in your Orgo 1 course. But the concepts and foundations learned in these reactions will carry through to the rest of your organic chemistry 1 and 2 courses.

Below is my alkene reaction mechanism tutorial video series taking you through each reaction 1 at a time, focusing on the WHY and HOW for every step in every mechanism starting with an understanding of pi bond reactivity, role of nucleophile/electrophile and even covering hydride shifts and ring expansions.

Alkene Reaction Study Guide Cheat Sheet

Alkene Reaction Study Guide Cheat Sheet

Included in this series:

  1. Introduction to nucleophile, electrophile and pi bond reactivity
  2. Hydrohalogenation
  3. Halogenation
  4. Halohydrin formation
  5. Acid Catalyzed Hydration
  6. Hydride Shift and Methyl Shift
  7. Ring Expansion via Hydride AND Methyl Shift
  8. Oxymercuration-Demercuration
  9. Alkoxymercuration-Demercuration
  10. Hydroboration Oxidation
  11. Alkene Epoxidation
    Cheat Sheet + Alkenes Quiz linked below the videos

Video 1 – Introduction to Nucleophile/Electronphile and Pi Bond Reactivity

Introduction to nucleophile electrophile and pi bond reactivity in alkene reaction mechanismsDon’t dismiss the intro video as ‘unimportant’ this may very well be the most important video in this series.

In this video you’ll get a proper view at the pi bond orientation and how this relates to alkene reactivity.

You’ll also learn the true meaning of Nucleophile and Electrophile, including how to recognize them and why they react as they do.

And finally, this video takes you through a sample alkene reaction mechanism focusing on they WHY and HOW to ensure you understand the movement of electrons every step of the way.

Video 2 – Hydrohalogenation Reaction Mechanism

Hydrohalogenation of alkenes reaction mechanism tutorial videoThe hydrohalogenation reaction is one in which the pi bond breaks adding a halogen to the more substituted carbon in keeping with Markovnikov’s rule.

This video takes you through the reaction and step by step mechanism for both a symmetrical starting alkene, and and asymmetrical starting alkene.

This mechanism typically involves hydrobromination and hydrochlorination in an inert solvent.

Carbocation rearrangements may be observed.

Video 3 – Halogenation of Alkenes Reaction Mechanism

Alkene Halogenation Reaction Mechanism Tutorial VideoThe alkene halogenation reaction is one in which the alkene pi bond breaks adding TWO halogen atoms to neighboring carbons. This occurs via a cyclic bromonium or chloronium intermediate.

This video helps you understand the step by step reaction mechanism, from the halogen reactivity, bridge formation, and overall anti addition.

Do not confuse this with the alkene hydrohalogenation which only ads a single halogen along with a hydrogen atom.

This video demonstrates the mechanism for a symmetrical and asymmetrical starting molecule.

Video 4 – Halohydrin Formation

Halohydrin formation alkene reaction mechanism tutorial videoThe halohydrin formation is an alkene reaction in which a halogen and an alcohol add to the broken pi bond.

This reaction starts out just like the halogenation reaction, but since it takes place in a reactive solvent, you get a solvent molecule partaking in the reaction mechanism.

This video provides with a step by step breakdown of the mechanism and helps you understand WHY this reaction undergoes anti addition and still follows Markovnikov’s rule.


Video 5 – Acid Catalyzed Hydration Alcohol Formation 

Acid catalyzed hydration alcohol formation alkene reaction mechanismAcid catalyzed hydration is the reaction in which an alcohol is added to a pi bond following Markovnikov’s rule.

This tutorial video gives you a step by step logical breakdown of every step in the reaction mechanism to ensure you understand WHY each atom attacks as it does.

This reaction covers the role of solvent and catalyst in hydration reactions, and well as regioselectivity in accordance with Markovnikov’s rule.

Practice problems included

Video 6 – Hydride Shift and Methyl Shift in Alkene Reactions

hydride shift methyl shift tutorial video

Video 7 – Ring Expansion Example with Hydride and Methyl Shift

coming soon

Video 8 – Oxymercuration-Demercuration of Alkenes

oxymercuration demercuration alkene reaction mechanism tutorial videoOxymercuration-Demercuration is an interesting alkene reaction in which the pi bond breaks to form an alcohol.

While this reaction is regioselective following Markovnikov’s rule, there is no carbocation rearrangement due to the mercurinium bridge formed in the intermediate.

This video takes you through the step by step reaction mechanism for oxymercuration and helps you understand WHY there is no carbocation rearrangement.

Video 9 – Alkoxymercuration – Demercuration of Alkenes

Alkoxymercuration Demercuration Reduction Alkene Reaction Mechanism Leah4sciAlkoxymercuration-Demercuration Reduction is the alcohol version of the oxymercuration reaction.

Just like its counterpart above, this reaction is regioselective in following Markovnikov’s rule and will not exhibit a carbocation rearrangement.

The product of this reaction is an ether as detailed in this tutorial video.


Video 10 – Hydroboration

click HERE for video

Video 11 – Alkene Epoxidation

Click HERE for video

Ready to test your skills? Click HERE for my FREE Alkene Reactions Practice Quiz

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Need a quick review of alkene reactions? 

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alkene reaction study guide cheat sheet