GOING GREEN

Can you help me understand Substitution and Beta-Elimination Reactions in Organic Chemistry?

Why does Beta elimination always compete with nucleophilic substitution? I dont understand. And how do I know which will happen, or more specifically, what would I write on a test? Im really confused on this topic and I can not figure it out. Please, if you can, clarify this for me. Thanks so much!

Substitution reactions can be described in two extremes, SN1, and SN2. In an SN1 reaction, the rate-limiting step is formation of a carbocation. The leaving group must pull the electrons from the carbon. It is assumed that no bond formation occurs until a carbocation exists long enough for the leaving group to diffuse away and the group having left does not influence any incoming nucleophile. If the RX compound had been optically active, then the product of the reaction would be completely racemic.

On the other extreme, we have an SN2 reaction. In an SN2 reaction, the bond formation precedes and controls the product formation. The nucleophile must push into the carbon nucleus. If the RX group were optically active, the product would retain that optical activity but it will be of the opposite configuration due to an inversion that takes place.

In between these extremes will be the reactions for which you have to predict the products and sometimes there are ambiguities or exceptions. Therefore, I find that predicting the products can be challenging. However, there are some simple principles,

An SN1 reaction requires conditions that favor carbocation formation, namely a good leaving group on a tertiary carbon, a polar solvent, usually water, and weak nucleophiles (often uncharged). Primary halides (unless allylic or benzylic) never undergo SN1 reactions. Tertiary halides never undergo an SN2 reaction.

SN2 reactions require conditions in which a pair of electrons are able to attack the carbon attached to the leaving group. That attack must precede bond cleavage. In order to extend the reach of the electrons, anions and especially anions of weak acids are common. High nucleophile concentrations and polar aprotic solvents (DMF, DMSO) are common.

The ease of nucleophilic substitution is: methyl halide>primary halide>secondary halide. Tertiary halides fail to react via SN2 mechanisms. In order to displace a tertiary halide, the halide must leave before the nucleophile can attack (Sn1 reaction).

Any factors that interfere with SN2 reactions will increase the amount of elimination. In Chapter 4, Examples 2, 3, and 5 result in elimination reactions. Elimination increases as steric hindrance to an SN2 reaction increases. In Example 3, tert-butoxide is a poor nucleophile due to its greater size. In Examples 2 and 5, the target carbon is more hindered by neighboring atoms and stereochemical factors that favor elimination. Secondary halides are more difficult to displace by an SN2 reaction and the conditions of the reaction are more important in predicting the products.

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