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Curved Arrows and Addition Reactions

February 15, 2013 By James Ashenhurst 4 Comments

The last two posts have been about a pretty amazing new concept. Not only can lone pairs act as nucleophiles…. but π bonds can too! Alkenes are a lot more exciting than they're often given credit for.  That means that given a sufficiently frisky electrophile, they can donate their pair of … [Read more...]

Filed Under: AlkeneCC, Alkenes Tagged With: alkenes, conventions, curved arrows, electrophiles, pi bonds

Nucleophilicity vs. Basicity

June 6, 2012 By James Ashenhurst 30 Comments

Following up on Nucleophiles and Electrophiles, here's a common question students have about nucleophilicity: What's the difference between nucleophicity and basicity? Great, great question. First of all, remember that basicity is a subset of nucleophilicity. All nucleophiles are Lewis … [Read more...]

Filed Under: Alkyl Halides, Organic Chemistry 1, Understanding Electron Flow Tagged With: acids, bases, basicity, electrophiles, kinetic, nucleophiles, nucleophilicity, rates, thermodynamic

Nucleophiles and Electrophiles

June 5, 2012 By James Ashenhurst 19 Comments

All through the series on understanding where electrons are, and how they flow, we've been talking about how the basis of chemistry is that opposite charges attract and like charges repel, and that in reactions, electrons flow from "electron rich" areas to "electron poor" areas. Today, we'll … [Read more...]

Filed Under: Alkyl Halides, Organic Chemistry 1, Organic Reactions, Understanding Electron Flow, Where Electrons Are Tagged With: acids, bases, electrophiles, electrophilicity, lewis acids, lewis bases, nucleophiles, nucleophilicity

Acid Base Reactions: What’s the Point?

May 30, 2012 By James Ashenhurst 2 Comments

One thing has been missing from our discussion of acid-base reactions. Who cares? What does it matter that we understand acid base reactions? Why is it important? Today, I hope to show that it matters a lot, not only for its own sake, but for topics that concern the rest of the … [Read more...]

Filed Under: Alcohols, Aldehydes, Functional Groups, Organic Chemistry 1, Organic Reactions, Understanding Electron Flow, Where Electrons Are Tagged With: acid, base, conjugate acid, conjugate base, electrophiles, nucleophiles

Reaction Friday: Friedel Crafts Acylation

March 2, 2012 By James Ashenhurst 10 Comments

Today's Reaction Friday is about the Friedel Crafts acylation of benzene and other aromatics, an important example of electrophilic aromatic substitution. One thing I forgot to say at the bottom is that there's several different ways of showing how the acyl halide is activated by Lewis acid - … [Read more...]

Filed Under: Organic Chemistry 2, Organic Reactions Tagged With: acid halides, acyl halides, AlCl3, aromaticity, aromatics, benzene, electrophiles, electrophilic aromatic substitution, FeCl3, Friedel-Crafts, mechanisms, Reaction Friday

Introduction to Nucleophilic Substitution Reactions

September 26, 2011 By James Ashenhurst 9 Comments

Following up on the 4 most important patters of reactions in Org 1, and introduction to acid-base reactions, here's the second major pattern. It's called nucleophilic substitution. I won't go into nucleophiles and electrophiles in this post. The point is actually not to understand what's going on … [Read more...]

Filed Under: Chemical Bonds, Organic Chemistry 1, Organic Reactions Tagged With: electrophiles, leaving groups, nucleophiles, nucleophilic substitution, sn1, SN2, substitution

Partial Charges Give Clues About Electron Flow

July 11, 2011 By James Ashenhurst 3 Comments

There's a hidden layer of detail beneath chemical structures that students new to organic chemistry often miss. I'm talking about partial charges. Although each of these bonds appears to be covalent, the electronegativity of each atom determines how "greedy" it is for electrons - and this … [Read more...]

Filed Under: Chemical Bonds, Functional Groups, Organic Chem Study Tips, Organic Chemistry 1, Where Electrons Are Tagged With: charges, electron density, electronegativity, electrophiles, hints, nucleophiles, partial charges

Common Blind Spot: Intramolecular Reactions

July 4, 2011 By James Ashenhurst 3 Comments

So I bought a belt today (pleather, 75 cents at the Goodwill).  and decided to show it off. This is me putting it together. This is what it looks like now: At this point you're probably saying WTF: that's not what a belt is supposed to look like when you put it together. That's because … [Read more...]

Filed Under: Drawing Reaction Mechanisms, Understanding Electron Flow Tagged With: electrophiles, fischer esterification, Friedel-Crafts, intramolecular, mental blocks, nucleophiles, rings, williamson

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