Semester Two 2016
Examination Period
Faculty of Pharmacy and Pharmaceutical Sciences
EXAM CODES: PSC1022
TITLE OF PAPER: Bioorganic and Medicinal Chemistry II – Paper 1
EXAM DURATION: 3 hours writing time
Section A Multiple Choice Questions [30 questions × 2 = 60 marks]
1. Rank the following molecules from most basic to least basic:
A I > II > III > IV
B IV > III > I > II
C I > III > IV > II
D IV > III > II > I
E I > IV > III > II
2. Which one of the following amines can be prepared using the Gabriel synthesis [i.e. using potassium phthalimide]?
3. What is the correct IUPAC name for the molecule below?
A N,N,2-trimethylhexanamine
B N,N-dimethyl-2-aminoheptane
C N,N-dimethylheptan-2-amine
D N,N-dimethyl-N(2)-heptylamine
E N,N,2-dimethylaminoheptane Page 3 of 20
4. Which one of the following reactions has a mechanism different from nucleophilic acyl addition?
A Reduction of a ketone with NaBH4
B Reaction of benzaldehyde with ethylmagnesium bromide
C Acid catalysed reaction of acetone and ethylene glycol (HOCH2CH2OH)
D Formation of the cyclic hemiacetal from 5-hydroxypentanal
E Esterification of butanol with acetic anhydride
5. What functional group(s) can be found in the acidic hydrolysis product of the compound below?
A alcohol and aldehyde
B alcohol only
C alcohol and ketone
D alcohol and carboxylic acid
E alcohol and ether
6. Which one of the following compound pairs represents a pair of tautomers?
7. Rank the following carboxylic acid derivatives in order of increasing their reactivity with benzylamine (the least reactive first):
A IV < III < II < I
B IV < III < I < II
C IV < I < II < III
D I < IV < II < III
E I < IV < II < III
8. Rank the following molecules from most acidic to least acidic:
A IV > II > I > III
B IV > III > I > II
C II > IV > I > III
D IV > II > I = III
E II > IV > I = III
9. Which is the correct structure of benzyl benzoate?
10. Which one of the following nucleophilic addition or substitution reactions proceeds well without acid catalysis?
A benzoic acid and ethanol (esterification)
B ethyl butanoate and water (hydrolysis)
C acetophenone and butylmagnesium bromide (Grigniard reaction)
D cyclohexanone and excess of methanol (acetal formation)
E methyl hexanoate and isopropanol (transesterification)
11. Which reagents are suitable for the transformation below?
A 1) thionyl chloride, 2) benzyl alcohol (phenylmethanol)
B 1) LiAlH4, 2) benzoyl chloride
C 1) water, H+, 2) benzoyl chloride
D 1) LiAlH4, 2) benzaldehyde
E 1) KMnO4, 2) benzyl alcohol (phenylmethanol)
12. Which one of the following compounds is the product of reaction between hexanoic acid and hexanamine in water at room temperature?
13. Which statement on Ziegler-Natta polymerisation is correct?
A Its mechanism involves free radical formation
B This method is applied for the synthesis of step-growth polymers
C Insertion of an alkene is one of the steps in this reaction
D This is a metal-catalysed oxidation by mechanism
E This reaction requires very high temperature
14. What is the correct classification of a polymer below?
A polyurethane
B polyester
C polyamide
D polycarbonate
E polyacrylate
15. The magnetic properties of a complex depend on
A the number of donor atoms
B the number of unpaired electrons
C the magnetic properties of the ligand
D options A and B
E options B and C
16. Ligands such as ethylenediamine are referred to as
A diandontate
B polyoate
C bidentate
D bidensate
E didentate
17. Which one of the following vitamins is NOT a lipid (lipophilic molecules)?
A Vitamin A
B Vitamin K
C Vitamin C
D Vitamin D
E Vitamin E
18. Which one of the following fatty acids is more likely to commonly occur in nature?
19. What will reaction of D-ribose (below) with LiAlH4 yield?
A a single chiral alditol
B a pair of enantiomeric alditols
C two diastereomers
D a meso compound
E a chiral salt of aldonic acid
20. Which one of the structures below corresponds to L-ribulose (a ketopentose)?
21. Assign the stereocentres in mannose (below) according to the S/R-system.
A 2R, 3R, 4R, 5R
B 2R, 3R, 4S, 5S
C 2R, 3S, 4R, 5S
D 2S, 3S, 4R, 5R
E 2S, 3R, 4S, 5R
22. Which term better describes the relationship of aldonic acids derived from D-glucose and L-glucose?
A a single chiral alditol
B two enantiomers
C two diastereomers
D a meso compound
E a chiral salt of aldonic acid
23. Which one of the following sets of amino acids contains only hydrophobic amino acids?
A Phe, Ser, Asp
B Met, Gly, Glu
C Val, Trp, Ile
D Val, Lys, Gly
E Arg, Phe, Trp
24. Peptapeptide Ala-Gly-Arg-His-Phe was treated with trypsin and chymotrypsin and then subjected to electrophoresis at pH = 7. Identify a fragment, which is formed from this pentapeptide and moved further to the cathode.
A Ala-Gly
B Ala-Gly-Arg
C Arg-His-Phe
D His-Phe
E Phe
25. Which one of the following dipeptides has a pI of (about) 3?
26. A complete hydrolysis of DNA gives the following pyrimidine bases:
A adenine and guanine
B uracil and thymine
C thymine and guanine
D cytosine and uracil
E cytosine and thymine
27. What kind of bond connects adenine and ribose within a strand of RNA?
A glycosidic bond
B hydrogen bond
C peptide bond
D phosphodiester bond
E purinoribosidic bond
28. What is the reaction mechanism between alkylators and DNA?
A free-radical addition
B electrophilic addition
C nucleophilic substitution
D oxidation of deoxyribose
E pi-pi stacking interactions with nucleobases
29. Which one of the following interactions of a drug and drug target is stronger?
A ionic
B hydrogen bonding
C covalent bonding
D dipole-dipole interactions
E pi-pi stacking interactions
30. Which one of the following biomolecules is NOT a common drug target?
A membrane phospholipids
B enzymes
C DNA
D nuclear receptors
E ion channels