A.

Synthesis and Purification

This experiment aimed to produce 2-naphthoxyacetic acid

from 2-naphthol and chloroacetic acid through Williamson ether

synthesis. This involved two separate reactions namely,

preparation of an alkoxide, then a reaction of this reagent with the

alkyl halide to produce an ether.

2-Naphthol was observed to be light brown in color with a

slight odor. Around 0.937 grams or 6.5 mmol of 2-naphthol was

dissolved in 7 mL of 10% (w/v) NaOH solution. In an SN2

reaction, a strong base is required for the mechanism to proceed

since this  will act as the nucleophile to produce a phenoxide.

Being a concerted reaction, the cleaving and bond formation all

happen simultaneously, a strong nucleophile is needed to attack

the carbon and to cause the leaving group to leave and also in

forming a stronger bond. 

The solids were dissolved via agitation and the resulting

solutions appeared as brown solution. This solution was then

poured into a micro-reflux setup. Sodium hydroxide which was

dissolved in water will dissociate almost completely into sodium

cations and hydroxide anions. 

NaOH (s) + H2O -> Na+(aq) + OH-(aq)

Figure 7.?? Reaction mechanism of NaOH dissolved in water

This reaction below would proceed upon dissolving 2-

naphthol in sodium hydroxide solution:

Figure 7.?? Reaction mechanism of 2-naphthol with NaOH

Hydroxide ion has a negatively charged oxygen atom which

carries great electron density that the oxygen atom in the neutral

2-naphthol molecule (Sodeberg), hence, the hydroxide ion would

serve as the nucleophile between 2-naphthol and hydroxide ion.

Hydroxide ion can strongly deprotonate the terminal H atom in the

2-naphthol molecule, yielding water and a negatively charged

naphthoxide ion with great electron density at the O atom.