The number of alkenesthat will form under E2 elimination for each of the given alkyl bromides are to be determined. Concept Introduction: > E2 elimination is a single step mechanism involving both the substrate and the base in the rate determining step. > The base extracts a β-proton from a carbon next to the carbon bonded to halogen. Simultaneously, the bond pair moves to form the pi-bond between these two carbon atoms, and the halogen leaves as halide ion, with its bond pair. > The number of products formed depends on the number of distinct β-carbon atoms bearing hydrogen atoms.

Question

Wintergreen from Aspirin: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? 2. Write the mechanism of the esterification reaction you did. 3. What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?

Answer 1

Question

Chapter 7, Problem 41P

Interpretation Introduction

Interpretation:

The number of alkenesthat will form under E2 elimination for each of the given alkyl bromides are to be determined.

Concept Introduction:
>
E2 elimination is a single step mechanism involving both the substrate and the base in the rate determining step.
>
The base extracts a β-proton from a carbon next to the carbon bonded to halogen. Simultaneously, the bond pair moves to form the pi-bond between these two carbon atoms, and the halogen leaves as halide ion, with its bond pair.
>
The number of products formed depends on the number of distinct β-carbon atoms bearing hydrogen atoms.

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