1. Select the dominant form of the amino acid proline at pH 8.
2. Solutions of the following optically active compounds are subjected to catalytic
hydrochloric acid in water. After this treatment, some solutions do not display optical
activity. Identify the compounds whose solutions retain optic...
The following practice exam contains questions from past final exams as well as new questions.
You will get the most out of this practice test if you complete it under EXAM CONDITIONS -
that is, without distractions and within a 2.5 hour time limit.
It is not possible to match the actual exam length exactly, but it is close. This test contains items
that sample from the learning objectives in the course, but does not test everything. The
difficulty level is also similar to the actual final exam. However, since the questions sample from
the course, the actual exam may feel more or less difficult to you, depending on how well you
know the various topics.
1
,Part 1. Multiple Choice.
1. Select the dominant form of the amino acid proline at pH 8.
O O OH O O
OH O OH O O
NH NH 2 NH NH N
A B C D E
2. Solutions of the following optically active compounds are subjected t
hydrochloric acid in water. After this treatment, some solutions do not d
activity. Identify the compounds whose solutions retain opticalactivity.
O O O O O
H H H H H
H HH H Me
A B C D E
3. Which structure will react most rapidly with ethoxide, when ethoxide a
nucleophile?
O O O O O
F Cl Br Me Et
O O O O O
A B C D E
HA
O N
4. Of the labeled atoms, identify the most nucleophilic E
B
NH2
atom in the following structure: C
D NO2
Cl A
B C
5. Of the labeled atoms, identify the most electrophilic
D
carbonatom in the following structure: O E O
H
2
, OH
H
CH2OH
HO O
Questions 6 to 12.
H 1 OH *
*
H O OH
Use the structure of the carbohydrate H
HO H O
derivative shown to the right to answer
H 2
these questions. H OH
H 3
O
O CH2OH
H3C CH3
6. Which of the following describes the three rings labeled 1, 2, a
Answer choice Ring 1 Ring 2 Ring 3
A Pyranose Pyranose Pyranose
B Furanose Furanose Furanose
C Pyranose Furanose Pyranose
D Furanose Pyranose Furanose
E Pyranose Pyranose Furanose
F Furanose Furanose Pyranose
G Pyranose Furanose Neither
H Furanose Pyranose Neither
I Neither Pyranose Neither
J Furanose Neither Neither
7. How many monosaccharides in this structure are based on ketoses?
A) 0 B) 1 C) 2 D) 3
8. Will this structure give a positive Tollen’s test result?
A) Yes B) No
9. Can this structure undergo mutarotation?
A) Yes B) No
10. To what functional group does the carbonatom labeled * belong?
A) aldehyde E) acetal
B) ketone F) ketal
C) hemiacetal G) alcohol
D) hemiketal H) ether
3
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