Adapted from PLTL
Names: ___________________
Chem 227/ Dr. Rusay
Carboxylic Acids
1. Circle the member of each of the following pairs that is more acidic.
a.
CH3COOH
versus
FCH2COOH
b.
CF3COOH
versus
CCl3COOH
c.
CH2=CHCH2COOH
d.
N≡C–CH2COOH
versus
versus
COOH
HC≡CCH2COOH
HC≡CCH2COOH
COOH
versus
e.
CH3
CF3
COOH
COOH
versus
f.
C
H
N
2. Circle the major species at equilibrium.
a.
C6H 5CO2H + H2O
b.
CH3 CO2
+ EtO2CCH 2CO2Et
OH
c.
CH3 CH
C
OH
C6H 5CO2
+ H3O
CH3 CO2H + EtO2CCHCO 2Et
O
CH3CH 2C
OH
Adapted from PLTL
4.
Use words and/or structures to explain the observations in each of the following
equations (solubility is water solubility):
OH
+ NaOH (aq)
insoluble
OH
+ NaHCO3 (aq)
insoluble
OH
+ NaOH(aq)
soluble
OH
+ NaHCO3 (aq)
insoluble
CO2H + NaOH (aq)
soluble
CO2H
soluble, formation
of gas bubbles
+ NaHCO3 (aq)
Using the observations of the reactions above, attach a flow diagram with structures
showing how products of the acid catalyzed hydrolysis of each of the respective esters,
which follow, can be separated by acid-base extraction techniques using methylene
chloride and any aqueous acids or bases that are necessary.
O
C
i.
O
O
C
ii.
O
Adapted from PLTL
5.
Complete the table that follows the synthetic conversions A thru K, specifying
necessary reagents and/or conditions.
A
B
C
Adapted from PLTL
D
E
F
G
H
I
J
K