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