Tuesday, December 3, 2013

For the Sapling solution discussion, I chose to do problem number 6 from chapter 9. The problem begins: Draw the major elimination product formed in the following reaction.

We know from the information given in the problem that this is an elimination reaction. By looking at the reagents we can see that it will be an E2 reaction because it is an aprotic solvent. This is a concerted mechanism meaning that it happens in one single step where the halide and the hydrogen are removed at the same time as the double bond is formed.

 When we look at the alpha carbon which has the halide attached to it, the carbons on this alpha carbon are called beta carbons. Zaitsev's rule states that the more substituted alkene product is formed when the proton is removed from the beta carbon bonded to the fewest number of hydrogens. For this problem however, we do not follow this rule because it will not give us the most stable product. Here we want to remove the hydrogen from the beta carbon with the most hydrogens because it will allow for more conjugation of the compounds can be seen below in the final answer.

1 comment:

  1. Very clear explanations and well organized. This post demonstrates a good understanding of E2 reactions, Zaitsev's rule, and alkene stability