WORKSHEET FOR CARBOXYLIC ACIDS AND ESTERS
1. How is the geometry of the carbonyl group different from the geometry around a carbon in an
alkane? Explain why.
2. Provide the IUPAC name for each of the following compounds.
HO
OH
O
Cl
C
C
HO
O
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OH
H2
C
O
CH
H2
C
H3C
CH
H3C
C
C
H2
OH
C
O
OH
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O
O
_________________________________
O
O
C
C
H3C
CH 3
_________________________________
H2
C
O
H2
C
C
H2
CH 3
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3. Using the Ka or pKa values, rank the acids in order from strongest (1) to weakest (2) acid.
Acid
Benzoic acid
Trichloroacetic acid
Acetic acid
Pentanoic acid
Hexanoic acid
Rank Solubility
Rank BP
4. Write the full or condensed structural formula for each of the following compounds.
Butyric acid
isopropyl hexanoate
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acetic acid
cyclopentyl benzoate
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2-hydroxy-3, 5-dimethyl heptanoic acid
phenyl pentanoate
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5a. Explain why acids are highly water soluble (even
more so than corresponding alcohols).
b. Explain what happens between carboxylic acid
molecules that significantly increases their boiling
points compared to comparable alcohols.
6.
Complete the following reactions and supply the appropriate reactant(s) or product(s).
+ KOH
OH
C
O
HO
CH 3
O
CH 3
C
+
C
H2
O
CH
___________________
H3C
C
O
C
H2
O
H2
C
C
O
H2
C
H2
C
CH
H3C
H2O
CH 3
LiAlH 4
OH
C
CH 3
O
CH 3
CH 3
heat
CH
______________________________
H2
C
H3C
H2
C
C
H2
H2
C
O
C
H2
H3C
C
O
CH3
NaOH
CH
O
C
C
O
O
CH 3
CH 3