Carboxylic Acid Practice Problems

Question 1

Using your knowledge of resonance and induction, draw the conjugate base of each of the following carboxylic acids and rank the acids by their relative acidity.

Most Acidic--->Least Acidic
Acid A
Acid B
Acid C
Acid A
Acid B
Acid C
Acid A
Acid B
Acid C

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Check Conjugate Base Structures


Question 2

Use the pKa values provided to rank the following diverse acids by their relative acidity.

Most Acidic--->--->--->Least Acidic
Acid A
Acid B
Acid C
Acid D
Acid E
Acid A
Acid B
Acid C
Acid D
Acid E
Acid A
Acid B
Acid C
Acid D
Acid E
Acid A
Acid B
Acid C
Acid D
Acid E
Acid A
Acid B
Acid C
Acid D
Acid E

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Question 3

Following are many of the reagents used to perform reactions on carboxylic acids. Select the carboxylic acid reaction type occurring upon addition of these reagents. (For additional practice you should draw the product that would be produced when each of these reagents reacts with 3-oxobutanoic acid.)

CH2N2 Acid/Base
Reduction
Esterification
Decarboxylation
Acyl Halide Formation
SOCl2 Acid/Base
Reduction
Esterification
Decarboxylation
Acyl Halide Formation
Heat Acid/Base
Reduction
Esterification
Decarboxylation
Acyl Halide Formation
CH3CH2CH2OH, H2SO4 Acid/Base
Reduction
Esterification
Decarboxylation
Acyl Halide Formation
POCl5 Acid/Base
Reduction
Esterification
Decarboxylation
Acyl Halide Formation
NaOH Acid/Base
Reduction
Esterification
Decarboxylation
Acyl Halide Formation
BH3/THF Acid/Base
Reduction
Esterification
Decarboxylation
Acyl Halide Formation

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Check Reaction Products


Last modified 3/31/97


Abby Parrill
Department of Chemistry
Michigan State University

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