Electrophilic Aromatic Substitution: Nitration of Phenacetin

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

1. 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.

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2. Although all EAS reactions proceed via the same two-step mechanism, it is the formation of the reactive electrophile that differs from reagent to reagent. Draw a reasonable electron-pushing arrow mechanism for the formation of the active nitration reagent. Then draw the mechanism for the actual EAS with the activated electrophile you will be using in this lab.




3. Is your starting material for this reaction (phenacetin) activating or deactivating? How do you know? What impact should this quality have on the ensuing nitration?

4. What regio selectivity do you expect for the nitration reaction?Why?Use electron- pushing arrows and resonance structures to help demonstrate your predicted reaction regio selectivity.

5. Using your answers from #1-4, reflect back and concisely summarize both the objective and the purpose of this experiment?

Results & Discussion:

6. For each characterization test you will perform, provide at least one specific piece of data that will indicate that your objective was fulfilled, and the expected product(s) were obtained. For each piece of data, explicitly state whether it shows that your reaction (a) went to completion, and/or (b) proceeded to give the expected regio specificity (i.e. how will you be able to distinguish the ortho product from the meta product).

7. For each possible regio isomeric product for Lab #3B, calculate (and clearly show your calculations for) the theoretical 1H NMR chemical shifts for all aromatic protons, and predict their corresponding multiplicities and J values.


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