Problem
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Aldol Self-Condensation
Draw the
structure of the aldol self-condensation product for each of the following compounds. If a compound
does not undergo aldol self-condensation, explain why it does not.
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1.
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Refer
to Aldol Self-Condensation.
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Reaction 23-1
Consider the reaction below to answer the following
question:
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2.
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Refer
to Reaction 23-1. Write the complete stepwise mechanism for the reaction above. Show all intermediate
structures and all electron flow with arrows.
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3.
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Refer
to Reaction 23-1. The product of this reaction is:
a. | a b, g-unsaturated aldehyde | b. | a a, b-unsaturated ketone | c. | an a, b-unsaturated aldehyde | d. | an enol | | |
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Mixed Aldol
Each of the following compounds can be prepared by a
mixed aldol condensation reaction. Give the structures of the aldehyde and/or ketone precursors for
each aldol product and formulate the reaction.
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4.
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Refer
to Mixed Aldol.
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Claisen Condensation
Draw the
structure of the product you would expect to obtain by Claisen condensation of each of the following
esters. If an ester does not undergo Claisen condensation, explain why it does not.
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5.
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Refer
to Claisen Condensation.
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Acetoacetic Ester
Consider the
reaction below to answer the following questions:
Acetoacetic ester can be prepared by the Claisen self-condensation
reaction of ethyl acetate.
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6.
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Refer
to Acetoacetic Ester. Ethyl acetate can be prepared from ethanol as the only organic starting
material. Show all reagents and structures for all intermediates in this preparation.
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2-methyl-2-carboethoxycyclopentanone
Consider the
compound 2-methyl-2-carboethoxycyclopentanone, whose structure is shown below, to answer the
following questions.
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7.
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Refer
to 2-methyl-2-carboethoxycyclopentanone. Formulate a synthesis of
2-methyl-2-carboethoxycyclopentanone starting with acyclic precursors using a Dieckmann cyclization
as a key carbon-carbon bond forming step. show all reagents and all intermediate
structures.
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Michael
Draw the structures of the precursors to each of the
following Michael reaction products. Label the Michael donor and the Michael acceptor in each case
and formulate the reaction.
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8.
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Refer
to Michael.
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9.
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Refer
to Michael.
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10.
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Refer
to Michael.
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