ORGANIC CHEMISTRY 2 (MCHA 021) EXAMINATION JULY, 2022

2022
QUESTION PAPER
SEFAKO MAKGATHO HEALTH SCIENCES UNIVERSITY
ASSESSMENT AND CERTIFICATION MANAGEMENT

SCHOOL OF SCIENCE AND TECHNOLOGY

SUBJECT NAME: ORGNIC CHEMISTRY 2 TYPE OF EXAMINATION: STANDARD X

RE-EXAMINATION

SUBJECT CODE: MCHA 021

COURSE: BSc 2 PAPER NUMBER: P1

NUMBER OF STUDENTS: 50

DATE OF EXAMINATION: 21 JULY 2022 DURATION: 3 HOURS

NUMBER OF STUDENTS: TOTAL MARKS: 100

INTERNAL EXAMINERS PARTICULARS: DR BR MASEKO; DR PM

NDAWUNI; MR MT OLVIER; MR
N MAKHUBELA

EXTERNAL MODERATOR PARTICULARS: 1. PROF BA DERIBIGBE(FORTHARE)

2.

THIS QUESTION PAPER CONSISTS OF (12) PAGES INCLUDING COVER PAGE.

Please confirm Please indicate the quantity

Stationary
Specified Instructions to students what you need per student

1. Answer ALL questions 4 PAGE BOOK x 4

2. Write neatly 8 PAGE BOOK

1
MCQ’s (must be supplied by the
3. Use MCQ paper for Section A department on day of submission)

4.
 2022 .

SEFAKO MAKGATHO HEALTH SCIENCES UNIVERSITY

SCHOOL OF SCIENCE AND TECHNOLOGY

SUBJECT NAME: ORGANIC CHEMISTRY 2 TYPE OF EXAMINATION: STANDARD X

RE-EXAMINATION
SUBJECT CODE: MCHA 021

COURSE: BSc 2 PAPER NUMBER: P1

DATE OF EXAMINATION: 21 JULY, 2022 DURATION: 100

SIGNATURE OF HEAD OF DEPARTMENT:

SIGNATURE OF DEAN OF SCHOOL:

CONTACT NUMBERS OF INTERNAL EXAMINERS

NAME CONTACT NUMBER

DR BR MASEKO 078 1103017
Mr MT OLVIER 072 660 8500
MR N MAKHUBELA
Dr PM NDAWUNI

CONTACT NUMBERS OF EXTERNAL EXAMINERS

NAME CONTACT NUMBER

PROF BA ADIREBGE 0603045357
SECTION A [25]

1. Which of the following statements

about elimination reactions is true?
A) Two  bonds are broken. C) Two  bonds are broken.

B) Two  bonds are formed. D) Two  bonds are formed.

2. What is the relationship between the following two compounds?

A) Constitutional isomers C) Stereoisomers

B) Identical D) Not isomers, different compounds

3 Which of the following is the definition of chirality?

A) The existence of a molecule with a mirror image.
B) The existence of a molecule with a carbon atom that has four different
substituents.
C) The existence of a molecule that is superimposable on its mirror image.

D) The existence of a molecule that is not superimposable on its mirror image.

4. Which of the following statements is true?

A) Enantiomers are mirror images that are not superimposable.
 B) A molecule that is superimposable on its mirror image is chiral.

C) A chiral molecule usually contains a plane of symmetry.

D) An achiral molecule does not contain a plane of symmetry.

5. Which of the following terms explain why aldehydes are more reactive than
ketones?
A) Electronegativity and resonance C) Electronegativity and hybridization

B) Hybridization and resonance D) Sterics and electronics

6. Is the following reaction reversible and, if so, under what conditions?

A) No C) Yes, using Pd/C

B) Yes, under acidic conditions D) Yes, under basic conditions

7. How can an unsaturated fatty acid be converted into a saturated fatty acid?
A) hydrogenation B) hydration C) ozonolysis D) hydrolysis

8. Which of the following is the repeating unit in polyvinyl chloride (PVC)?

 A) A B) B C) C D) D

9. What would happen if a mixture of benzoic acid and cyclohexanol dissolved in

CH2Cl2 is treated with aqueous NaOH solution?
A) Benzoic acid would remain in the CH 2Cl2 layer, and cyclohexanol would
dissolve in the aqueous layer.
B) Benzoic acid would dissolve in the aqueous layer while cyclohexanol would
remain in the CH2Cl2 layer.
C) The salt of benzoic acid would dissolve in the aqueous layer while
cyclohexanol would remain in the CH2Cl2 layer.
D) The salt of benzoic acid would remain in the CH 2Cl2 layer while
cyclohexanol would dissolve in the aqueous layer.

10. Which is the correct Haworth projection for the alpha anomer of D-glucose?
 A) A B) B C) C D) D

11 Which of the following is the correct structure for alanine at pH = 7?

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.

B) Because the ketone will be protonated and thus unreactive.

C) Because the ketone will form an unreactive enol.

D) Because the Grignard reagent won't dissolve in aqueous solutions.

14. What is the direct product of the base-promoted hydrolysis of an ester?

A) A nitrile B) A carboxylic acid C) An amide D) A carboxylic acid salt

15. What is the IUPAC name of the following compound?

A) (Z)-4-hexen-1-amine C) (E)-2-hexen-6-amine

B) (E)-4-hexen-1-amine D) (Z)-2-hexen-6-amine

16. Which of the following compounds is conjugated?

AI B II C III D IV

17 Which of the following statements about the structure of benzene is not

true?
A) Benzene is planar.
B) Benzene has three short double bonds alternating with three longer single
bonds.
C) The electrons in the pi bonds are delocalized around the ring.
D) Benzene has six pi electrons

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

19. What is the name of the following compound?

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

SECTION B [80 Marks]

INSTRUCTIONS:
1 ANSWER QUESTION 1 IN THE SPACES PROVIDED.
2 USE THREE SEPARATE ANSWER SHEETS TO ANSWER QUESTION 2, 3 and 4

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)

(iii) Draw all the other stereoisomers of (-) –ephedrine.

(2)
 (iv) How are the above stereoisomers related to (-) –ephedrine? (2)

(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)

(e) Draw a stepwise mechanism for the following reaction. (4)

hv
+ Br
NBS
Br
QUESTION 2 [20]

(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

(e) Arrange the following acids in increasing strength of acidity (1)

 O
O Br
Br O
O
OH
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

(d) Given the peptide synthesis reaction below: (6)

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]

a) Considering the anti-corona virus medication drawn below (Dimethyl-[3-(3-nitro-

phenylcarbamoyl)-phenyl]-(3-phenylamino-phenyl)-ammonium) an isolated compound from
a medicinal plant from Lusiki-siki in Eastern Cape province (South Africa). After the structure
elucidation of the compound, it was found that the drug has several benzene rings identified
as A, B, C and D. According to the electrophilic aromatic substitution select:
i) Which of these rings is the most reactive in electrophilic aromatic substitution.
(1)
ii) Which of these rings is the least reactive in electrophilic aromatic substitution
(1)
b) Use the Intramolecular Friedel-Crafts acylation reaction to explain the mechanism of the
most probable product (major product) among the two formed (A and B) following chemical
transformation below. Give the reason. (6)

c) 2-tert-butyl-4-methoxyphenol, known as Butylated Hydroxyanisole (BHA) is a synthetic

antioxidant commonly used as food preservative. This powerful organic compound can be
developed from benzene-1,4-diol (p-benzene diol) via 4-methoxyphenol. Derive the
synthetic route of the formation of BHA. (Use para isomer when para and ortho are formed).
(4)

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)

e) Retrosynthesis is the process of “deconstructing” a target molecule into readily available

starting materials by means of imaginary breaking of bonds (disconnections) and by the
conversion of one functional group into another functional group. What organic starting
materials are needed to synthesise the compound below by reductive amination? (2)