Question

1. In the first step of the mechanism for this process, a phenoxide anion is generated. This phenoxide anion goes on to act as a nucleophile via an SN2 mechanism, displacing the chloride on 3-chloro-1,2-propanediol. Why doesn’t the phenoxide anion act as a base to deprotonate one of the alcohols on 3-chloro-1,2-propanediol? Write a brief, specific explanation (1-2 sentences).

Answer 1

Answer:

See the explanation

Explanation:

In this case, in order to get an elimination reaction we need to have a strong base. In this case, the base is the phenoxide ion produced the phenol (see figure 1).  

Due to the resonance, we will have a more stable anion therefore we will have a less strong base because the negative charge is moving around the molecule (see figure 2).

Finally, the phenoxide will attack the primary carbon attached to the Cl. The C-Cl bond would be broken and the C-O would be produced at the same time to get a substitution (see figure 1).