MCAT and Organic Chemistry Study Guides & Tutoring

Proton Transfer and Rearrangement Mechanisms in Organic Chemistry

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Mechanisms in Organic Chemistry Tutorial Video Series by Leah4Sci part 2Proton transfer and rearrangements are 2 more common mechanism patterns you will face in organic chemistry.

This is in addition to Nucleophilic attack and Loss of Leaving Group discussed in Mechanism Video Part 1.

You’ll see multiple proton transfer examples in action including turning a bad leaving group into a good leaving group!

Rearrangement mechanism are broken down for a step-by-step comparison of stability to explain WHY hydride shifts or methyl/alkyl shifts occur to facilitate carbocation stability!

(Watch on YouTube: Mechanisms Part 2. Click cc for video transcription.)

Links & Resources Mentioned In This Video:

<– Watch Previous Video: Mechanisms Part 1
–> Watch Next Video (Coming soon): Mechanisms Part 3

This is Video 2 in the Mechanisms Series. Click HERE for the entire series.

SN1 Reaction Mechanism with Hydride Shift and Carbocation Rearrangement Part 3

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SN1 Reaction Mechanism with Hydride Shift and Carbocation Rearrangement Part 3 Tutorial VideoSN1 SN2 E1 Series: Video 11
In this final SN1 video you’ll see tricky examples involving less substituted carbocation intermediates followed by carbocation rearrangements and hydride shifts.

When working through these reactions pay special attention to the patterns that help determine the SN1 mechanism over a potential SN2 or E2


(Watch on YouTube: SN1 Part 3. Click CC on bottom right for transcript.)

<– Watch Previous Video: SN1 Reaction Mechanism Examples of Unimolecular Substitution Part 2
–> Watch Next Video: SN2 Reaction Rate and Mechanism Bimolecular Substitution Part 1

This is Video 11 in the Nucleophilic Substitution and Beta Elimination Video Series. Click HERE for the entire series & cheat sheet!

Ready to test your substitution/elimination skills? Try my FREE SN1 SN2 E1 E2 Practice Quiz.

Ring Expansion via Hydride Shift and Methyl Shift

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Ring expansions occur as a carbocation rearrangement when an unstable cycloalkane is near a carbocation. You will come across ring expansion mechanisms during alkene reactions and later in SN1 and E1 reactions.

They key is to recognize when a ring is unstable, and the type of rearrangement that will help it become more stable. But don’t stop there. Ring expansions may be followed by a 1,2-hydride or 1,2-methyl shift.

The video below takes you through a tricky reaction mechanism taken from a students actual exam.

(Watch this video on YouTube or read the transcript coming soon)

Watch the previous video: Hydride Shift Methyl shift mechanism

Watch next video: Oxymercuration-Demercuration Reduction

Return to: Alkene Reaction Mechanisms Home Page

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

Hydride Shift and Methyl Shift Mechanism

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hydride shift methyl shift tutorial videoHydride shifts and methyl shifts can occur in organic chemistry reactions if there is a carbocation intermediate. While Markovnikov’s rule placed the carbocation on the more substituted of the 2 former sp2 (double bound) carbon atoms, if there is an EVEN MORE substituted carbon nearby you’ll get a carbocation rearrangement.

This video helps you understand the logic behind the carbocation rearrangement, along with specific patterns to look for when deciding between a hydride shift or methyl shift.

(watch this video or YouTube or view the transcript – coming soon)

Click for previous video – Acid Catalyzed Hydration

Next video: – ring expansion

This is video 6 in the Alkene Reaction Mechanism series. Click to see the entire series

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

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