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Understanding Ortho, Para, and Meta Directors

February 2, 2018 By James Ashenhurst Leave a Comment

In the previous post we introduced ortho- ,para- and meta- directors in electrophilic aromatic substitution.  Previous to that we covered the mechanism of electrophilic aromatic substitution, and showed that the mechanism proceeds through a carbocation intermediate. Today, we're going to tie … [Read more...]

Filed Under: Aromatic Reactions, Organic Chemistry 2 Tagged With: activating, carbocation stability, deactivating, directing groups, electrophilic aromatic substitution, meta, nitration, ortho, para, reaction energy diagram

Hybridization And Bond Strengths

January 19, 2018 By James Ashenhurst 4 Comments

Understanding the concept of hybrid orbitals lets you make accurate predictions about trends in bond strengths. In this post we'll give several examples of how to do this. Let's start with a quick quiz. What's the strongest C–H bond, below? (In other words, which C–H bond has the highest … [Read more...]

Filed Under: Chemical Bonds, Organic Chemistry 1 Tagged With: acidity of alkynes, bond dissociation energy, bond strength, carbocation stability, hybridization, pi bonds, radical stability, sigma bonds

The E1 Reaction

September 19, 2012 By James Ashenhurst 5 Comments

Last time in this walkthrough on elimination reactions, we talked about two types of elimination reactions. In this post, we're going to dig a little bit deeper on one type of elimination reaction, and based on what experiments tell us, come up with a hypothesis for how it works. Here's the … [Read more...]

Filed Under: Alkenes, Alkyl Halides, Organic Chemistry 1, Organic Reactions, Understanding Electron Flow Tagged With: alkenes, alkyl halides, base, carbocation stability, e1, elimination, mechanism, primary, rate laws, secondary, tertiary

Comparing the SN1 and SN2 Reactions

August 8, 2012 By James Ashenhurst 93 Comments

Hey! You can now download a free 1-page Summary Sheet of SN1 vs SN2 reactions containing all the material on this series of blog posts here: Download SN1 vs SN2 Summary Sheet PDF   Since we've gone through the different factors that impact the SN1 [see post] and SN2 [see post] … [Read more...]

Filed Under: Alcohols, Alkyl Halides, Organic Chemistry 1, Organic Reactions, Stereochemistry Tagged With: backside attack, carbocation stability, leaving groups, nucleophiles, sn1, SN2, steric hindrance, substitution

7 Factors that stabilize negative charge in organic chemistry

February 27, 2012 By James Ashenhurst 18 Comments

Like I wrote about last time, it's good - but not enough - to recognize partial charges and to figure out where they interact. Since reactions involve processes that lead to the gain or loss of charges, understanding the factors that stabilize (or destabilize) charge have a tremendous impact on … [Read more...]

Filed Under: Organic Chemistry 1, Understanding Electron Flow Tagged With: acidity, basicity, carbanions, carbocation stability, charge stability, electron density, electron withdrawing groups, formal charge, polarizability, resonance

Introduction to Rearrangement Reactions

October 17, 2011 By James Ashenhurst 7 Comments

The previous four posts on acid-base, substitution, addition, and elimination covered the 4 main reactions in organic chemistry I. Now it's time to go beyond those mainstays to introduce a few of the less common (but still important) reactions you learn in organic chemistry 1. They will be … [Read more...]

Filed Under: Organic Chemistry 1, Organic Reactions Tagged With: 1-2-shifts, addition, carbocation stability, carbocations, elimination, rearrangements, substitution, wagner meerwein

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