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문제 2a
Give an example for each of the following:
a. a β-keto nitrile
문제 2b
Give an example for each of the following:
b. a β-diester
문제 2c
Give an example for each of the following:
c. a β-keto aldehyde
문제 3
Explain why a base can remove a proton from the α-carbon of N,N-dimethylethanamide but not from the α-carbon of either N-methylethanamide or ethanamide.
문제 4
Explain why the -hydrogen of an N,N-disubstituted amide is less acidic (pKa = 30) than the -hydrogen of an ester (pKa = 25).
문제 5a
Rank the compounds in each of the following groups from strongest acid to weakest acid:
a.
문제 5c
Rank the compounds in each of the following groups from strongest acid to weakest acid:
c.
문제 6
Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water.
문제 7d,e
Draw the enol tautomers for each of the following compounds. For compounds that have more than one enol tautomer, indicate the one that is more stable.
d.
e.
문제 7f
Draw the enol tautomers for each of the following compounds. For compounds that have more than one enol tautomer, indicate the one that is more stable.
f.
문제 10
A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the ⍺-carbon. All of these reactions have similar rate constants.What does this tell you about the mechanisms of these reactions?
문제 11a
Show how the following compounds can be prepared from the given starting material:
a.
문제 14a
How could each of the following compounds be prepared from a ketone and an alkyl halide?
a.
문제 14b
How could each of the following compounds be prepared from a ketone and an alkyl halide?
b.
문제 16a
How could each of the following compounds be prepared from cyclohexanone?
a.
문제 16b
How could each of the following compounds be prepared from cyclohexanone?
b.
문제 17a
Describe how the following compounds could be prepared from cyclohexanone using an enamine intermediate:
a.
문제 17b
Describe how the following compounds could be prepared from cyclohexanone using an enamine intermediate:
b.
문제 18a
Draw the products of the following reactions:
a.
문제 18b
Draw the products of the following reactions:
b.
문제 19a
What reagents should be used to prepare the following compounds?
a.
문제 19b
What reagents should be used to prepare the following compounds?
b.
문제 19c
What reagents should be used to prepare the following compounds?
c.
문제 20a
What aldol addition product is formed from each of the following compounds?
a.
문제 20b
What aldol addition product is formed from each of the following compounds?
b.
문제 24
How could you prepare the following compound using a starting material that contains no more than three carbons?
문제 25a
Describe how the following compounds can be prepared using an aldol addition in the first step of the synthesis:
a.
문제 25b
Describe how the following compounds can be prepared using an aldol addition in the first step of the synthesis:
b.
문제 25c
Describe how the following compounds can be prepared using an aldol addition in the first step of the synthesis:
c.
문제 26
What two carbonyl compounds are required for the synthesis of morachalcone A, via a Claisen–Schmidt condensation?
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