6.Draw: methyl cis-3-ethylcyclobutanecarboxylate
8.Name:
____________________________________________
8.
9. Name:
_____________________________________________
10.Name:
___________________________________________
11.Name:
______________________________________________
Questions 15 -17: Consider the data in the Table below to answer the following question(s):
16.
Acidities of Substituted Benzoic and Acetic Acids
pKas at 25C
YC6H4COOH
Y
meta
YCH2COOH
H
4.75
4.19
CN
2.47
3.64
OCH3
3.57
4.09
Which of the acids in the table above has the strongest conjugate base?
______________________________
para
4.19
3.55
4.46
19 Explain the differences in acidity between p-methoxybenzoic acid and m-methoxybenzoic
acid.
When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting
mixture is acidified, phenylacetic acid is produced. Any unreacted benzylmagnesium bromide is
converted to toluene in the acidification step.
a.
b.
c.
d.
20.
Write the complete reaction sequence for the process described above.
21.
How could you separate phenylacetic acid from toluene?
22.
This reaction is described as a _____ process.
carbonylation
carboxylation
Carbaniolation
cationation
Circle one: a
b
c
d
Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all
relevant stereochemistry.
26.
Question 28:
What is the order of decreasing reactivity towards nucleophilic acyl substitution for the carboxylic acid
derivatives? (most reactive first)
28.
a.
b.
c.
d.
I, II, III, IV
I, III, IV, II
II, IV, III, I
II, I, III, IV
Circle one: a
b
c
d
Questions 31 and 32: Consider the reaction below to answer the following question(s):
Acid halides react with diazomethane to yield diazoketones. Excess diazomethane is used to prevent the
HCl produced in the reaction from reacting with the diazoketone.
31. Diazomethane is an example of a dipolar molecule; a molecule which is neutral overall but has charges on
individual atoms. One resonance form of diazomethane is drawn below. Draw the Lewis structure of the
other resonance form of diazomethane. Be sure to include all formal charges.
32. The intermediate structures for the mechanism for the reaction of propanyl chloride with diazomethane
are provide below. Show all electron flow with arrows on these structures.
33. Methyl butanoate has been isolated from pineapple oil and can be prepared by the Fischer esterification
reaction shown below. Write the complete stepwise mechanism for this reaction. Show all electron flow
with arrows and include all intermediate structures.
34. The purpose of the acid catalyst in the hydrolysis of an amide is:
a.
b.
c.
d.
to enhance the nucleophilicity of the water molecule
to enhance the electrophilicity of the amide carbonyl carbon
to enhance the electrophilicity of the water molecule
to shift the equilibrium of the reaction
Circle one: a
b
c
d
Questions 35 - 37: Consider the information below to answer the following question(s).
The reaction of a carboxylic acid with an alcohol in the presence of acid is termed Fischer esterification.
35. The nucleophile in this reaction is _____.
36.
Compound C functions as _____ in this reaction.
a.
b.
c.
d.
a base scavenger
a solvent
a catalyst
a neutralizer
Circle one: a
b
c
d