6-35 a - Organic Chemistry (Mcmurry)

Question

Follow the flow of electrons indicated by the curved arrows in each of the following polar reactions, and predict the products that result:

Step-by-Step Solution

Answer

(a) 

                         Curved arrow representation 

Attack of hydroxide ion

The hydroxide ion attacks the hydrogen of the alcohol. This results in deprotonation to form water and an alkoxide. Next, the bonding pair of electrons flow down to the oxygen that had its hydrogen removed.

Formation of carbon-carbon double bond

These bonding pairs of electrons form a carbon-oxygen double bond. This new bond forces the methoxy group to leave as methoxide. The leaving group is negatively charged because wherever the arrow stops is where the charge ends up. Thus, the curved arrow representation is as shown:

                      Curved arrow representation