Download Winter 2004 Final Exam

Memorial University of Newfoundland
Chemistry 2440 Final Exam
April 2004
S. V. Pansare
Name:__________________
Time: 2 ½ hours
Student Number:__________________
[Marks]
1. Give a brief description and provide a suitable example of each of the following:
a) Markovnikov’s rule
b) An aromatic substitution reaction
c) Acetal formation
d) A polyamide (a condensation polymer)
e) Diastereomers
f) An irreversible enzyme inhibitor
[12]
2. Give IUPAC names for the following compounds
[8]
OH
Cl
b)
a)
Br
H3CH2CO
OCH3
F
b)
a)
c)
CH2CH3
O
O
CH3
c)
O
d)
HO
CH3
d)
3. Draw molecules with the formula C5H10 (one for each part) which match the following
a) an alkene which is a trans compound
c) an alkene which does NOT have cis/trans forms
d) a cis compound which is not an alkene
[6]
4. Provide structures for the following compounds:
[8]
a) Ser-Lys-Pro
b) 2-Deoxy-D-ribose (Draw the open chain form as a Fischer projection)
c) Glutamine
d) Cytosine
5)
a) Draw the linear form of D-glucose as a Fischer projection and circle the carbon which is
inspected to determine that the configuration is ‘D’.
b) Draw the two cyclic forms of D-glucose in Haworth type drawings and label ‘α’ and ‘β’
c) Which from of D-glucose is normally the most stable in an aqueous solution; linear, ‘α’, or
‘β’?
d) Draw the structure of propyl-β-D-glucoside.
[5]
5. Complete the following reactions. Show stereochemistry where applicable.
a)
[12]
AlCl3
+
Cl
H2SO4
b)
heat
OH
c)
+
major
+
minor-1
minor-2
solvent
Br2
HBr
d)
e)
+
Ph
O
H2O, H+
O
+
warm
OH
f)
g)
+
H2O
NaOH
H
N
+
aqueous HCl
O
+
heat
6. A) Aspartame, an artificial sweetener which is marketed as NutraSweet®, has the structure
given below. Answer the following questions about Aspartame.
[7]
O
HO
H
N
H2N
O
O
Aspartame
a) Locate and name the functional groups in aspartame
b) Name the amino acids in aspartame
O
B) Ibuprofen, a popular non-prescription anti-inflammatory drug, has the structure given below.
Answer the following questions about ibuprofen.
[3]
OH
O
Ibuprofen
a) Circle the chiral carbon or carbons in ibuprofen, if any.
b) How would you convert ibuprofen to its methyl ester?(show the reaction, reagents, conditions)
7. A) What is the substrate for each of the following enzymes:
a) Maltase
b) fructose oxidase
c) sucrase
d) phenolase
[4]
8. B) What is an enzyme active site? What types of forces hold a substrate at an enzyme active
site?
[4]
9.
[6]
a) Provide the base sequence in the complementary RNA strand if a portion of one strand of
DNA has the following base sequence:
5’-AGTCCAGGT- 3’
b) Explain why the base sequence ATC could not be a codon
c) In terms of hydrogen bonding, a G-C base pair is more stable than an A-T base pair.
Explain.
10. The following questions are based on your laboratory work
a) What is the bromine test used for? Write a reaction to explain how the test works.
[5]
b) List three detection methods used for visualizing colourless organic compounds on TLC
plates
11. In the space provided, place the letter corresponding to a structure below which best fits the
description or name.
[10]
Answer
Description or name
_____
Serotonin
_____
A neurotransmitter
_____
A triose
_____
A sugar found in RNA
_____
The most abundant steroid in humans
_____
Adenine
_____
progesterone
_____
Histidine
_____
A base found in DNA
_____
D-mannose
NH2
OH
HO
N
NH2
N
N
H
HO
HO
HO
H
H
N
(B)
(A)
CHO
H
H
OH
OH
CH2OH
O
HO
HO
(C)
CHO
O
H
H
HO
OH
(E)
(D)
O
O
OH
NH2
HO
O
NH
NH2
N
H
O
(F)
OH
(G)
N
H
HO
(H)
(I)
O
N
H
(J)
12. Write short notes on any two of the following topics:
a) Chlorofluorocarbons and the ozone layer
b) Diabetes, aldehyde oxidation and glucose testing
c) Aspirin
d) Enzymatic browning: Discolouration of fruits and vegetables
[10]