The Williamson Ether Synthesis:

Conversion of Acetaminophen into Phenacetin

Unit 15 (read pages 323-325 of Experimental Organic Chemistry)

Introduction: Make sure you address each of the questions below when writing your

Introduction. Although for the pre-lab you may answer the questions separately, in your

final report, all of these points must be addressed in paragraphs, in a clear, cohesive,

and logical fashion.

1. Concisely summarize both the objective and purpose for Experiment #3A.

2. Draw the electron-pushing arrow mechanism for the reaction performed in

Experimental: You are not required to add an Experimental Section to your final

laboratory report. However, you must still answer these questions regarding your

experimental procedure in your pre-lab.

3. Draw a flow chart that clearly outlines how the primary product of your reaction will

be separated from the reaction mixture and isolated. The flow chart should include

all organic and aqueous extractions, and when applicable, denote which layer is the

top layer and which is the bottom layer. Intermediary boxes should include the

specific chemical(s) that are in that layer.

4. The Williamson ether synthesis is a simple two-step (1) acid/base reaction followed

by a (2) nucleophile/electrophile reaction. Why are they very useful for benzyl halide

and primary alkyl halide electrophiles, but often fail for secondary, tertiary, and aryl

halide electrophiles? What products might you expect if your electrophile in this

reaction was i-PrBr?.