{"id":1011,"date":"2020-02-17T22:22:00","date_gmt":"2020-02-17T22:22:00","guid":{"rendered":"http:\/\/box5250.temp.domains\/~aceorgan\/blog\/?p=1011"},"modified":"2020-02-20T17:25:51","modified_gmt":"2020-02-20T17:25:51","slug":"carbocation-stability","status":"publish","type":"post","link":"https:\/\/www.aceorganicchem.com\/blog\/carbocation-stability\/","title":{"rendered":"Carbocation Stability [with free study guide]"},"content":{"rendered":"\n

Carbocation stability<\/strong><\/h1>\n\n\n\n

Before we start talking about carbocation stability, we should have a starting discussion about some carbocation basics.<\/p>\n\n\n\n

What is a carbocation?<\/strong><\/h3>\n\n\n\n

A carbocation, also sometimes referred to as the carbonium ion, is an sp2 hybridized carbon atom with three groups bonded to it and a empty orbital.  Because it has an empty orbital, the sp2 carbon carries a positive charge on it, making it highly electrophilic (want to know more about electrophiles<\/a>?  Check out this blog post).  The geometry of the carbocation is trigonal planar, meaning all bond angles are 120\u00b0.  The empty orbital allows for the cation to be attacked from either side.  Hence, in many cases, a loss of chirality will occur if the starting material was chiral and the mechanism goes through a carbocation intermediate (Like an SN1 reaction).<\/p>\n\n\n\n

\"carbocation<\/figure><\/div>\n\n\n\n

How do we get carbocations?<\/strong><\/h3>\n\n\n\n

There are several ways to obtain a carbocation, but the first thing to understand is that carbocations are not inherently stable.  Translation<\/u>: You will not find a bottle of carbocations just sitting on the shelf.<\/p>\n\n\n\n

\"\"
This isn’t a thing<\/figcaption><\/figure><\/div>\n\n\n\n
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Shocking, i know<\/figcaption><\/figure><\/div>\n\n\n\n

The most common way to get a carbocation is through heterolytic cleavage of a carbon-heteroatom bond, where the heteroatom gets both electrons in the bond.  The heteroatom is sometimes referred to as a \u201cleaving group\u201d and is an atom (or molecule even) that can easily carry a negative charge.  Some examples of this type of carbocation formation are below:<\/p>\n\n\n\n

\"\"<\/figure><\/div>\n\n\n\n

The other way to form a carbocation is through the first step of electrophilic addition to a double bond.  The most common electrophile to add is a proton.  In this method, the proton adds to one side of the double bond, creating a carbocation on what used to be the other side of the double bond.<\/p>\n\n\n\n

\"\"<\/figure><\/div>\n\n\n\n

How do we stabilize carbocations?<\/strong><\/h4>\n\n\n\n

Now that we are all on the same footing, let\u2019s talk about carbocation stability.  There are three major ways to do this:<\/p>\n\n\n\n