carbocations

Making Alkyl Halides From Alcohols

Making Alkyl Halides From Alcohols

February 27, 2015

Making Alkyl Halides From Alcohols In today’s post we show that treating alcohols with HCl, HBr, or HI (which all fall under the catch-all term “HX” where X is a halide) results in the formation of a…

Read the full article →
Rearrangements in Alkene Addition Reactions

Rearrangements in Alkene Addition Reactions

February 26, 2013

In exploring reactions that proceed along the carbocation pathway, every once in awhile you might see an example of an addition reaction that looks a little… strange. The alkene is gone, two new bonds have formed, b…

Read the full article →
Rearrangement Reactions (2) – Alkyl Shifts

Rearrangement Reactions (2) – Alkyl Shifts

August 22, 2012

In the last post we saw how certain carbocations can sometimes rearrange (through hydride shifts)to give more stable carbocations. However, sometimes there are situations where a hydride shift would not lead to a more…

Read the full article →
The Conjugate Acid Is A Better Leaving Group

The Conjugate Acid Is A Better Leaving Group

August 7, 2012

One of the key factors that determines whether a nucleophilic substitution reaction will happen or not is the identity of the leaving group. Previously, we’ve seen that good leaving groups are weak bases. That m…

Read the full article →
The SN1 Mechanism

The SN1 Mechanism

July 13, 2012

Previously we saw that there are two important classes of nucleophilic substitution reactions, which differ in their rate laws, dependence on substitution pattern, and the stereochemistry of the products.  Having gon…

Read the full article →
Evaluating Resonance Forms (4): Positive Charges

Evaluating Resonance Forms (4): Positive Charges

December 14, 2011

As I mentioned before, the resonance form(s) of lowest energy are those where the charges are minimized. However, sometimes you can’t get around it: you have to put a charge somewhere. Last time I talked about t…

Read the full article →
Introduction to Rearrangement Reactions

Introduction to Rearrangement Reactions

October 17, 2011

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…

Read the full article →
Three Factors that Destabilize Carbocations

Three Factors that Destabilize Carbocations

March 21, 2011

In the recent post about 3 things that stabilize carbocations, I mentioned that carbocations are stabilized when their neighboring atoms donate electrons. This makes sense, right? Opposite charges attract, like charg…

Read the full article →
3 Factors That Stabilize Carbocations

3 Factors That Stabilize Carbocations

March 11, 2011

If electrons were money, carbocations would be the beggars of organic chemistry. Packing a mere six valence electrons, these electron-deficient intermediates figure prominently in many reactions we meet in organic che…

Read the full article →
Are these molecules conjugated?

Are these molecules conjugated?

March 8, 2011

If Org 2 has an overall theme, it’s “resonance”. Today’s post has a very simple message. Atoms with lone pairs, π bonds, radicals, and carbocations can participate in resonance: atoms that la…

Read the full article →