TAILIEUCHUNG - Ebook Organic chemistry as - A second language (3th edition): Part 2

(BQ) Part 2 book "Organic chemistry as - A second language" has contents: Substitution reactions, elimination reactions, addition reactions, alcohols, synthesis, retrosynthetic analysis, Predicting solubility of alcohols,.and other contents. | CHAPTER 9 SUBSTITUTION REACTIONS In the last chapter we saw the importance of understanding mechanisms. We said that mechanisms are the keys to understanding everything else. In this chapter, we will see a very special case of this. Students often have difficulty with substitution reactions—specifically, being able to predict whether a reaction is an SN2 or an SN1. These are different types of substitution reactions and their mechanisms are very different from each other. By focusing on the differences in their mechanisms, we can understand why we get SN2 in some cases and SN1 in other cases. Four factors are used to determine which reaction takes place. These four factors make perfect sense when we understand the mechanisms. So, it makes sense to start off with the mechanisms. THE MECHANISMS Ninety-five percent of the reactions that we see in organic chemistry occur between a nucleophile and an electrophile. A nucleophile is a compound that either is negatively charged or has a region of high electron density (like a lone pair or a double bond). An electrophile is a compound that either is positively charged or has a region of low electron density. When a nucleophile encounters an electrophile, a reaction can occur. In both SN2 and SN1 reactions, a nucleophile is attacking an electrophile, giving a substitution reaction. That explains the SN part of the name. But what do the “1” and “2” stand for? To see this, we need to look at the mechanisms. Let’s start with SN2: R1 Nuc H R2 LG - LG H Nuc R1 R2 On the left, we see a nucleophile. It is attacking a compound that has an electrophilic carbon atom that is attached to a leaving group (LG). A leaving group is any group that can be expelled (we will see examples of this very soon). The leaving group serves two important functions: 1) it withdraws electron density from the carbon atom to which it is attached, rendering the carbon atom electrophilic, and 2) it is capable of stabilizing the negative charge .

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