6-35b - 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

(b) 

                        Curved arrow representation

Attack of hydroxide ion

The hydroxide ion attacks the hydrogen of the methyl. This results in deprotonation to form water and a carbanion. Next, the bonding pair of electrons flow down from the carbon that had its hydrogen removed.

Formation of carbon-carbon double bond

These bonding pairs of electrons form a carbon-carbon double bond. This new bond forces the carbon-oxygen double bond to migrate up to the oxygen to form an oxyanion. The oxygen is negatively charged because wherever the arrow stop is where the charge ends up. Thus, the curved arrow representation is as shown:

                            curved arrow representation