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Office Use Only
Semester Two (November) 2014
Examination Period
Faculty of Pharmacy and Pharmaceutical Sciences
UNIT CODE: PSC1022
TITLE OF PAPER: Bioorganic and Medicinal Chemistry II
EXAM DURATION: 3 hours writing time
READING TIME: 10 minutes
THIS PAPER IS FOR STUDENTS STUDYING AT:
Berwick
Clayton
Malaysia
Off Campus Learning Open Learning
Caulfield
Gippsland
Peninsula
Enhancement Studies Sth Africa
Parkville
Other (specify)
During an exam, you must not have in your possession, a book, notes, paper, electronic device/s,
calculator, pencil case, mobile phone or other material/item which has not been authorised for the
exam or specifically permitted as noted below. Any material or item on your desk, chair or person
will be deemed to be in your possession. You are reminded that possession of unauthorised
materials, or attempting to cheat or cheating in an exam is a discipline offence under Part 7 of the
Monash University (Council) Regulations.
No exam paper or other exam materials are to be removed from the room.
AUTHORISED MATERIALS
OPEN BOOK
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NO
CALCULATORS
YES
NO
If ‘YES’ has been selected, only scientific calculators with a "Monash University, Faculty of
Pharmacy and Pharmaceutical Sciences Approved" sticker attached are permitted in examinations
for Pharmacy and Pharmaceutical Science students. No graphic calculators will be permitted.
SPECIFICALLY PERMITTED ITEMS
YES
NO
if yes, items permitted are:
Candidates must complete this section if required to write answers within this paper
STUDENT ID: __ __ __ __ __ __ __ __ DESK NUMBER: __ __ __ __ __
Section A [60 marks] + Section B [96 marks] = 156 marks Section A Multiple Choice Questions [30 questions 2 = 60 marks]
RECORD YOUR ANSWERS TO THESE QUESTIONS ON THE SEPARATE MULTIPLE CHOICE
ANSWER SHEET PROVIDED.
1. Ligands such as ethylenediamine are referred to as:
A bidentate
B bidenated
C tridentate
D bidensate
2. The correct name for [CoCl(NH3)5]SO4 is:
A chloridopentaamminecobalt(III) sulfate
B pentaamminechloridocobalt(III) sulfate
C chloridopentaamminecobalt(II) sulfate
D pentaamminechloridocobalt(II) sulfate
3. Chlorpromazine is an anti-psychotic agent. What is the classification of the amines I and II?
A I: primary aliphatic; II: primary aromatic
B I: tertiary aliphatic, II: primary aromatic
C I: tertiary aliphatic, II: tertiary aromatic
D I: tertiary aromatic, II: tertiary aliphatic
Page 2 of 17 4. Rank the following from most basic to least basic:
A II, III, I, IV
B IV, III, II, I
C I, III, IV, II
D III, IV, I, II
5. Which is the correct structure for diphenylamine?
A I
B II
C III
D IV
6. Many nucleophilic addition reactions of aldehydes and ketones are accelerated by acid or
base. Acids catalyse these reactions by:
A shifting the equilibrium of the reaction
B making the carbonyl group less electrophilic
C reacting with base produced during the reaction
D making the carbonyl group more electrophilic
E activating the nucleophile
Page 3 of 17 Page 4 of 17
7. Arrange the compounds in order of increasing boiling point (lowest first).
A III, I, IV, II
B I, II, IV, III
C III, IV, I, II
D II, I, III, IV
E None of the above
8.
Which is the main product from the reaction of (S)-2-methylpentanal with an aqueous base?
A I
B II
C III
D IV
9. Which compound reacts with aqueous acid to give an aldehyde?
A a
B b
C c
D d 10. Which of the following is a characteristic reaction of carboxylic acids and their derivatives?
A acetalisation
B nucleophilic acyl substitution
C nucleophilic acyl addition
D electrophilic substitution
11. What is the IUPAC name for the following compound?
A 2-oxohexanoic acid
B 5-oxohexanoic acid
C methyl butyroxo ketone
D 5-ketohexanoic acid
12. Which compound is prepared by reaction of benzoic acid with ammonia and water?
A a
B b
C c
D d
13. Arrange the compounds in order of increasing acidity (lowest first).
A IV, I, II, III
B III, II, IV, I
C IV, II, I, III
D II, I, III, IV
E None of the above
Page 5 of 17 14. Which is the correct structure for phenyl benzoate?
A a
B b
C c
D d
15. Which is the product of the reaction of phthalic anhydride with methanol?
A a
B b
C c
D d
E None of the above
Page 6 of 17 16. Which is the final product of a series of reactions starting with ethyl benzoate and reacting
with 1) aqueous sulfuric acid and heat, 2) thionyl chloride, and 3) ethylamine?
A a
B b
C c
D d
17. Which physical property of triacylglycerols rich in unsaturated fatty acids is responsible for
the lower melting point than the corresponding saturated compounds?
A hydrophobic attractions
B hydrophilic interactions
C cis-carbon-carbon double bond steric interactions
D hydrogen bonding
E increased interactions with water
18. Which reagents could be used to harden an oil to a fat?
A NaBH4 / H2O
B Ni / H2
C Ag(NH3)2
+
/ H2O
D Cu2+ / buffer
E heat
19. How many stereocentres are present in methandrostenolone (below)?
A 4
B 5
C 6
D 8
Page 7 of 17 20. Phospholipids are an abundant class of natural lipids and make up about 40-50% of cell
membranes. A phospholipid is derived from phosphatidic acid by esterification of the
phosphate group with an alcohol. Which of the following is NOT one of the most common
alcohols found in phospholipids?
A choline
B cholesterol
C inositol
D ethanolamine
21. Which polymers are correctly matched to their primary use?
I) Kevlar and containers
II) Polymethylmethacrylate and Plexiglas
III) Polytetrafluoroethylene and non-stick coatings
IV) PET and bulletproof vests
A I, III
B II, III
C II, IV
D III, IV
22. Which classification best describes the mechanism of the synthesis of polyamides via step
growth polymerization?
A nucleophilic acyl addition
B nucleophilic acyl substitution
C electrophilic addition
D radical substitution
23. What kind of bonds connect nucleotides within a strand of DNA?
A glycosidic bonds
B hydrogen bonds
C peptide bonds
D phosphodiester bonds
Page 8 of 17 24. What is the relationship between the following compounds?
A enantiomers
B anomers
C meso compounds
D diastereomers
25. Assign the stereocentres in D-Galactose according to the S/R-system.
A 2R, 3R, 4R, 5R
B 2R, 3R, 4S, 5S
C 2R, 3S, 4S, 5R
D 2S, 3S, 4R, 5R
26. What will reduction of D-fructose (below) with NaBH4 yield?
A a single chiral alditol
B two diastereomers
C a pair of enantiomeric alditols
D a meso compound
Page 9 of 17 27. Which is the DNA complement for 5’-ACCGTTAAT-3’?
A 5’-ATTAACGGT-3’
B 5’-GTTACCGGC-3’
C 5’-TGGCAATTA-3’
D 5’-CAATGGCCG-3’
28. Which is the order of increasing percentage in cells of messenger RNA, transfer RNA,
ribosomal RNA (least first)?
A mRNA, tRNA, rRNA
B tRNA, rRNA, mRNA
C rRNA, tRNA, mRNA
D mRNA, rRNA, tRNA
29. Which sequence of one-letter codes correctly represents the following hexapeptide?
A TSYLMT
B TSYKMT
C TMLYST
D TMKYST
E TSFKMT
30. Which is the structure of the pentapeptide that gave lys-leu-phe on reaction with cyanogen
bromide, and gave fragments met-lys, leu-phe, and arg on reaction with trypsin?
A arg-met-phen-leu-lys
B lys-leu-phe-arg-met
C arg-met-lys-leu-phe
D met-arg-lys-leu-phe
EXAMINATION CONTINUES OVER PAGE
Page 10 of 17 Section B Written Answer Questions [96 marks]
ANSWER QUESTIONS ONE TO TEN IN THE BOOKLET PROVIDED.
START EACH QUESTION ON A NEW PAGE.
QUESTION ONE
The amine shown below can be prepared from benzyl bromide.
(a) Give reaction(s), mechanism(s) and reagents that would allow you to complete this
transformation in good yield.
(b) What is the IUPAC name for this amine?
[6 + 1 = 7 marks]
QUESTION TWO
Predict the magnetic properties of the [Fe(CN)6]
3– complex anion. Justify your answer.
Data: Fe3+ is a d5
ion; CN–
is a strong-field ligand.
[5 marks]
Page 11 of 17 QUESTION THREE
Metals interactions with Aβ peptide in amyloid plaques are associated with Alzheimer’s disease
(AD) [“Alzheimer’s disease & metals: therapeutic opportunities”, V. B. Kenche and K. J. Barnham,
British Journal of Pharmacology 2011, 163, 211-219]. Compounds, which prevent these
interactions, may have potential as disease modifying strategies for treating AD. Clioquinol (shown
below) has moderate affinity for metal ions and has been tested in clinical trials against AD.
(a) Name the donor atoms in the functional groups, which enable this molecule to bind to
transition metal ions.
(b) What is the term used to describe the action of this compound when it forms a coordination
complex?
(c) Draw and classify two isomeric forms of the complex which could be formed between two of
these organic molecules and a copper (II) ion.
[2 + 2 + 6 = 10 marks]
QUESTION FOUR
Consider the following chemical transformations.
a) Draw structures of products (1), (2), and (3).
b) Give the IUPAC name for compound (1).
c) Reaction of (1) gives product (2). Describe type of this reaction on the basis of the
chemical transformation involved and the reaction mechanism.
d) Name functional groups in compound (3).
[6 + 1 + 2 + 2 = 11 marks]
Page 12 of 17 QUESTION FIVE
Consider the following chemical transformations.
1) Draw structures of products (1), (2), (3), and (5).
2) What is reagent (4)?
3) Give the IUPAC name for compound (1).
4) Name the functional group(s) in compound (2).
[8 + 2 + 1 + 1 = 12 marks]
QUESTION SIX
(a) Show with chemical equations how soaps can be made from triglycerides.
(b) Why is hard water problematic for triglyceride derived soaps?
(c) Would you expect the following fatty acids to occur naturally? Explain your answer for each
in 1-2 sentences.
[2 + 1 + 4 = 7 marks]
Page 13 of 17 QUESTION SEVEN
Given the following structure, determine the polymer’s repeating unit; redraw the structure using
simplified parenthetical notation, and name the polymer.
[4 marks]
QUESTION EIGHT
(a) The chair conformation of β-D-glucopyranose is unusual in that all the substituents are
equatorial. Draw the chair conformations of both α- and β-D-glucopyranose and their
corresponding Haworth projections, ensuring that you label each diagram.
(b) Draw the Fischer projection for the compound resulting from treatment of L-glucose with
silver nitrate, and name the compound.
[6 + 4 = 10 marks]
Page 14 of 17 QUESTION NINE
Given the structures of the deoxynucleotides below, redraw these structures to indicate the
arrangement of the Watson-Crick base pairs between them.
[6 marks]
Page 15 of 17 QUESTION TEN
Part A. The diagram below shows the binding mode of an analogue of the statin drug rosuvastatin
into the active site of the enzyme HMG-CoA reductase. Seven important intermolecular
interactions are shown numbered 1 through to 7. Also in the active site is a water molecule
(labelled 8) which resides next to the ethyl side chain on the pyrimidine ring and is also adjacent to
the side chain of leucine 562.
Provide a descriptive name for each of the seven intermolecular interactions.
Part B.
Order the seven intermolecular interactions from weakest to strongest. [e.g. 6 < 3 and so forth].
Part C.
For the interaction labelled 3 (aspartate, 690) suggest an alternative functional group to replace the
alcohol group (OH) that would result in a stronger interaction. Name this new interaction.
Page 16 of 17 Part D.
For the water molecule labelled 8, which resides next to the ethyl side chain on the pyrimidine ring
and leucine 562, suggest an alternative group to the ethyl group which could then displace the
water molecule and allow the new group to further interact with the leucine 562 residue. Either
name the group you intend to replace with the ethyl group or draw the structure in your exam
booklet. Briefly explain the reasoning behind your choice.
Explain the advantage of displacing the water molecule.
[7 + 7 + 2 + 8 = 24 marks]
END OF EXAMINATION
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