Description
Q 1. The aryl ketone 3 is prepared by a Friedel-Crafts acylation reaction. Identify the
preferred starting reactants (A and B) that you would use then illustrate a mechanistic
rationale for how your reaction proceeds (show arrows). Clearly show arrows, formal
charges, and stereochemistry in all intermediates. Show all resonance structures. Do not use
abbreviations such as R or Ar in intermediates or final structures.
Q 2. Predict the product from the following reaction. Only one equivalent of NH3, and an
excess of NaCNBH3 is necessary for this reaction. Provide a mechanism for the formation of
that product. Clearly show arrows, formal charges, and stereochemistry in all
intermediates. Do not use abbreviations such as R or Ar in intermediates or final structures.
Q 3. This dipeptide 1 is treated under the conditions described below in two steps. Show
the mechanism for the expected conversions in each step and be sure to indicate the
product 2 to be isolated. (Hint: the isolated product has an excellent chromophore (highly
conjugated) therefore it is readily detected with UV light.) Clearly show arrows, formal
charges, and stereochemistry in all intermediates. Show all resonance structures. Do not use
abbreviations such as R or Ar in the final structure.
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