Microsoft word - hw7 revised.doc

Homework 7 Questions
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Nomenclature (1 pt)
1. Potassium (2E,4E)-2,4-hexadienoate is added as a preservative to certain foods to prevent
bacteria and mold from causing food spoilage. Draw a structural formula of potassium (2E,4E)-
Acidities (1 pt)
2. In each of the following pairs below, which compound would have the higher pKa?

Synthesis (4 pts)
3. Predict the products of the following reactions:
hint: the product gives a peak in the IR at
Reactions of Acid Derivatives (3 pts)

4. Predict the products of the following reactions.

Mechanisms (2 pts)
5. A urethane is a molecule where the carbonyl is part of an ester and an amide. Propose a
mechanism for the formation of the following urethane.
Synthesis (6 pts)
6. Synthesize the following compounds using only benzene, carbon dioxide, 1-propanol as
sources of carbon.

Applications (3 pts)
7. Diphenyhydramine was one of the first known antihistimines. It is marketed under the brand
name Benadryl. Propose a synthesis starting from benzene, benzoic acid, and 2-(N,N-


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