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Ester Synthesis and Reaction Problems

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1. Consider the reaction sequence below to answer the following questions:

Compound X, diethyl propanedioate, is more commonly known as_____.

2. Consider the reaction sequence below to answer the following questions:

The starting material A in this reaction sequence is called a ______.

Conversion of A into B is a type of reaction termed ______.

Conversion of B into C involves hydrolysis of the ester followed by
decarboxylation. On the structures provided below, show the electron flow for the
decarboxylation step.

3. Give the major organic product(s) of each of the following reactions or sequences
of reactions. Show all relevant stereochemistry.

4. Consider the reaction below to answer the following questions:

This reaction is an example of:

The product of this reaction is:

5. 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.

6. Consider the reaction below to answer the following questions.

Which carbonyl compound functions as the electrophile in this reaction?

Draw the structure of the enolate ion that is generated during the course of this reaction.

This reaction is an example of :

7. Consider the reaction below to answer the questions that follow :
Acetoacetic ester can be prepared by the Claisen self-condensation of ethyl acetate.

Ethyl acetate can be prepared from ethanol as the only organic starting material. Show all reagents and structures for all intermediates in this preparation.

8. A multistep synthesis can be used to prepare 3,3-dimethylindanone. From the list provided below, choose the best reagent(s) for each step in this sequence. Place the letter in the box over the reaction arrow.
a. , HOAc

b. 0.05 equiv. NaOEt, ethanol, heat

c. 1. PhMgBr, ether,
2.

d. 1. Mg, ether
2.
3.

e. , NaOH,

f. , *

g. 1. , ether
2.

h. 1. LDA, THF
2. (CH3)2CHBr

i. ,

9. Methamphetamine can be synthesized by reacting 1-phenyl-2-propanone with methylamine in the presence of H2/Ni

A

Identify the nucleophile in the initial reaction of phenyl-2-propanone to yield intermediate A.

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