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Standard Examination July 2022for Study2023
Standard Examination July 2022for Study2023
2022
QUESTION PAPER
SEFAKO MAKGATHO HEALTH SCIENCES UNIVERSITY
ASSESSMENT AND CERTIFICATION MANAGEMENT
RE-EXAMINATION
NUMBER OF STUDENTS: 50
2.
4.
2022 .
5. Which of the following terms explain why aldehydes are more reactive than
ketones?
A) Electronegativity and resonance C) Electronegativity and hybridization
7. How can an unsaturated fatty acid be converted into a saturated fatty acid?
A) hydrogenation B) hydration C) ozonolysis D) hydrolysis
10. Which is the correct Haworth projection for the alpha anomer of D-glucose?
A) A B) B C) C D) D
A) A B) B C) C D) D
12. How can you convert a carboxylic acid into an acid chloride?
A) Heat with hydrochloric acid C) React with sodium chloride
B) React with thionyl chloride (SOCl2) D) React with Cl2 and FeCl3
13. Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the
addition of a Grignard reagent to a ketone?
A) Because the Grignard reagent will react with the acid and be quenched.
A) (Z)-4-hexen-1-amine C) (E)-2-hexen-6-amine
B) (E)-4-hexen-1-amine D) (Z)-2-hexen-6-amine
18. What are the two effects that have to be considered to determine the
influence a substituent will have on electrophilic aromatic substitution?
A) Steric and electronic C) Inductive and resonance
B) Inductive and steric D) Resonance and electronic
A) meta-bromophenol
B) para-hydroxybenzene
C) 3-bromoanisole
D) 6-methoxy-2-bromobenzene
20. What is the major organic product obtained from the following sequence of
reactions?
A) I B) II C) III D) IV
QUESTION 1 [20
Marks]
Give examples to clearly illustrate the meaning of the following terms and expressions. (6)
(a) Polymerization of the styrene when benzoyl peroxide is used as an initiator. Use at least
three monomers (2)
(b) Use 2-propanone as one of your starting material to synthesize an internal alkene as
using a Wittig reaction (2)
(c) Draw the structure of the principal product for each of the reaction below:
(2)
(d) Avocado (persea Americana Mill) is a species that contain oil cells in leaves, seeds, roots and
fruits. However, in the fruit, a higher percentage of oil was reported by many researchers including
Mr Mkhombo Zibusiso, a former Masters student in the School of Science and Technology at
Sefako Makgatho Health Sciences University. Mr Mkhombo further reported that the avocado
seeds contain many biologically active alcohols, some of which are monohydroxylated,
dihydroxylated and polyhydroxylated. The biologically active monohydroxylated compounds
including two stereoisomers, ephedrine and pseudophedrine which have two stereogenic centers
as shownin the structure below was isolated by Mr Mkhombo from avocado oil using column
chromatography. Ephedrine is one component of a once popular combination of drug used by body
builders to increase the energy and alertness, while pseudoephedrine is a nasal decongestant. (10)
(i) Draw the structure of the naturally occurring (-) –ephedrine which was isolated from
avocado seeds and has a configuration of 1R,2S. (1)
(ii) Draw the structure of the naturally occurring (+) –pseudoephedrine, one of the
stereoisomers of (-) –ephedrine, which was isolated from avocado seeds and has a
configuration of 1S,2S. (1)
(v) When the solution of (-) –ephedrine was placed in a polarimeter, the observed
rotation was _8.05o. The solution was made by diluting 0,40 g of the product to a total of
120 mL and the solution was placed into a 600 nm polarimeter. Calculate the optical
rotation (4)
(a) Benzoic acid, the simplest benzene-based carboxylic acid, has been known since the 16th
century. One of its discoverers was the legendary clairvoyant Nostradamus. Its most
common natural source is gum benzoin, a resin found in the bark of trees of the genus
Styrax. Most benzoic acid produced today is synthetic. Benzoic acid's antimicrobial activity
is primarily against yeasts and molds. Like most organic acids, antimicrobial activity is
greatest at low pH. The effect results from greater permeability of the unionized form into
microorganisms. A group of BSc 2 students from Sefako Makgatho Health Sciences
University performed a study on the biological activities of benzene derivatives, including the
ester below. (7)
(i) Write the stepwise mechanism for the Fischer esterification reaction that was used to
prepare the ester above. (5)
(ii) One of the students accidentally added acidified water instead of pure water in an
endeavour to purify the product before drying it. Write the principal products that
were formed. (2)
(iii) Benzoic acid can be synthesized from benzonitrile. Propose a mechanism for the
acid-catalyzed hydrolysis of benzonitrile to benzamide. (4)
(iv) Two widely used pain relievers are aspirin and acetaminophen which are derivatives
of benzene. Show how would you synthesize acetaminophen from phenol. (4)
H O
N C CH3
HO
(b) Which is the major product formed in the reactions below? (4)
O
ethanol
O
heat
(c) Which combination of a carbonyl compound and Grignard Reagents can be used to
prepare the alcohol below (3)
(d) What is the IUPAC name for the following compound? (1)
O OH
OH Br Br OH
A B C D
QUESTION 3 [25]
(a) Convert each compound to a Fischer projection and label each sterogenic center as R or S
configuration. (4)
(i)
HO O
C
CH3 C Br
H
(ii)
Cl
C H
CH3CH2
Br
(b) Treating a monosaccharide with an alcohol and HCl converts the hemiacetal to a glycoside.
Give a detailed mechanism of how β-D-glucose, below, can be converted to the glycoside
acetals B and C, where B is the α glycoside and C the β glycoside. (6)
HO
HO O HCl
OH B + C
HO CH3CH2OH
OH
(c) Using the structures of the amino acids Gly, His and Leu, give the reaction that shows the
formation of following peptide. Label the N-terminal and C-terminal amino acids and all amide
bonds. (5)
Gly-His-Leu
O- O
H3+N H3 N+
+
O O-
Ala Gly
(i) Use the amino acid abbreviations (Ala and Gly) to give all the possible products that can
be formed from the reaction above. (4)
(ii) Choose any one of your products in 4.4.1. above and briefly explain how you would selectively
synthesize the product. (2)
(e) The terpene molecule below is that of squalene (shark oil); (4)
squaline
(shark oil)
(i) How many isoprene units that it have?
(1)
(ii) How many C-C bonds are needed to join the units in 4.5.1. above? Use an arrow to
indicate at least one of the bonds. (2)
(ii) To what class of terpenes does the above molecule belong? (1)
QUESTION 4 [20]
d) Which one of the following three amines can be prepared by the Gabriel synthesis: 2,2-
dimethyl-1-propanamine, 3-methyl-1-pentanamine, or N-butylaniline? Propose an alkyl
halide that can be used as starting material for this synthesis, and explain why the other two
amines cannot be prepared this way. (6)