Departement Chemie

Department of Chemistry

CHM 215
Eksamen / Examination
Organiese & Fisiese Chemie / Organic & Physical Chemistry

12/06/2012 Tyd / Time: 150 min

Punte / Marks: 100

INTERNE EKSAMINATORE / INTERNAL EXAMINERS: Dr S Bauermeister, Dr M Nkwelo,

Dr H Badenhorst
EKSTERNE EKSAMINATORE / EXTERNAL EXAMINERS: Prof R Vleggaar
Dr E du Toit

Finale Punt: / Final Mark:

Voorletters & Van: / Initials & Surname: ______________________________________

Studentenommer: / Student Number: ___________________________

Handtekening: / Signature: __________________________________

Telefoonnommer: / Telephone number: __________________________________

__________________________________________________________________________

Algemene Instruksies:
1. Beantwoord beide Afdelings direk op die vraestel. Indien ‘n antwoord nie in die gegewe spasie
gegee word nie, moet die nuwe posisie duidelik aangetoon word. Kanselleer antwoorde wat
nie gemerk moet word nie met pen.
2. Finale antwoorde moet in blou of swart pen gegee word.
3. Selfone moet afgeskakel word.
4. Sien aparte nota oor die bekendmaking van die finale punte asook insae in gemerkte
eksamenantwoordstelle.
General Instructions:
1. Answer both Sections directly on the question paper. If an answer is not given in the space
provided, clearly indicate location. Cancel answers that should not be marked with pen.
2. Final answers should be given in blue or black pen.
3. Cell phones must be switched off.
4. See separate note regarding the announcement of the final marks as well as viewing of
marked exam scripts.

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AFDELING 1: ORGANIESE CHEMIE / SECTION 1: ORGANIC CHEMISTRY [75 (+4)]

Punte / Marks

Instruksies:
1. Tensy anders gespesifiseer, gebruik lynstrukture waar strukture vereis word.
2. Gebruik geboë pyle om verwante resonansstrukture te genereer en waar meganismes gevra
word.
Instructions:
1. Use line structures where structures are required, unless specified otherwise.
2. Use curved arrows to obtain related resonance structures and where mechanisms are
requested.
__________________________________________________________________

Vraag 1 / Question 1 (8 punte / marks)

1.1 Benaam die volgende verbindings soos gespesifiseer:

Name the following compounds as specified:

a) ‘n Volledige IUPAC sistematiese naam: (3)

A complete IUPAC systematic name: (3)
CHO
OH
O

______________________________________________________

b) ‘n Algemene (triviale) naam: (1) / A common (trivial) name: (1)

OH
OH
O
_____________________________________________________

1.2 a) Teken ‘n lynstruktuur van N-metiel-δ-laktaam: (2)

Draw a line structure for N-methyl-δ-lactam: (2)

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 b) Teken ‘n lynstruktuur vir die bensielester van asynsuur: (2)
Draw a line structure for the benzyl ester of acetic acid: (2)

Vraag 2 / Question 2 (4 punte / marks)

‘n Verteenwoordigende segment van ‘n poliamied word hieronder getoon. Teken die

lynstrukture van die hidroliseprodukte na verhitting in waterige suur.
A representative segment of a polyamide is shown below. Draw the line structures of the
hydrolysis products after heating in aqueous acid.

O O

H H N N
N N H H

O O

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Vraag 3 / Question 3 (9 punte / marks)

3.1 Maak gebruik van strukture van toepaslike tussenprodukte en/of oorgangstoestande en
verduidelik waarom die onderstaande substraat beide E1 en E2 reaksies kan ondergaan.
(6)
Make use of structures of appropriate intermediate products and/or transition states and
explain why the substrate given below could undergo both E1 and E2 reactions. (6)

Brr
B

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3.2 Eters kan deur ‘n SN2 reaksie van alkoksiede (RO¯) met alkielhaliede berei word. Watter
een van die twee onderstaande moontlike sintese roetes sou jy verkies? Verduidelik. (3)
Ethers can be prepared by SN2 reaction of alkoxides (RO¯) with alkyl halides. Which of
the two possible synthetic routes shown below would you prefer? Explain. (3)
_
_
O
O
H3II
CCH3

oeettee 11
RRo
Roouuttee 11
R
OC H3
CH
O 3

_
_
II H3O
CCH O
3

Rooeettee 22
R
Roouuttee 22
R

Vraag 4 / Question 4 (4 punte / marks)

Teken ‘n orbitaaldiagram met gepaste byskrifte waarin die plasing van al die ring π elektrone
asook die valenselektrone van die heteroatome duidelik aangetoon word om die verskille en
ooreenkomste in die basisiteit van die drie N atome in triasool aan te toon.
Draw an annotated orbital diagram to show the placement of all the ring π electrons as well
as the valence electrons of the heteroatoms to show the similarities and differences in
basicity of the three N atoms in triazole.

N NH

N
triasool / triazole

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Vraag 5 / Question 5 (8 punte / marks)

Gebruik die onder gegewe vier substituente en teken lynstrukture van die vier para-
gesubstitueerde bensoësuurderivate in volgorde van swakste tot sterkste suur. Gebruik
enkele strukture, geboë pyle, resonans- en induktiewe effekte met kort beskrywings om jou
antwoord te verduidelik.
Use the four substituents given below and draw line structures of the four para-substituted
benzoic acid derivatives in order from the weakest to the strongest acid. Use some
structures, curved arrows, resonance and inductive effects with short descriptions to explain
your answer.

Substituente: / Substituents:

CN OH CH3 C(O)CH3

Suurheidvolgorde: / Order of acidity:

Verduideliking: / Explanation:

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Vraag 6 / Question 6 (13 punte / marks)

6.1 Gebruik lynstrukture, geboë pyle, resonans- en induktiewe effekte met kort beskrywings
om die effek van die substituent in metielbensoaat (Verbinding B) op die reaktiwiteit in
elektrofiele aromatiese substitusiereaksies sal hê, te verduidelik. (6)
Use line structures, curved arrows, resonance and inductive effects with short
descriptions to explain the effect the substituent in methyl benzoate (Compound B)
would have on the reactivity in electrophilic aromatic substitution reactions? (6)

O
O

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6.2 Die –NH2 en –Br groepe is beide orto/para-rigtend in elektrofiele aromatiese substitusie
reaksies, maar die –NH2 groep is aktiverend, terwyl die –Br deaktiverend is, d.w.s.
anilien is baie meer reaktief as bromobenseen. Verduidelik. (3)
The –NH2 and –Br groups are both ortho/para-directing in electrophilic aromatic
substitution reactions, but the –NH2 group is activating whereas the –Br is deactivating,
i.e. aniline is much more reactive than bromobenzene. Explain. (3)

6.3 p-Tolueensulfoonsuur word gevorm wanneer tolueen in die para-posisie gesulfoneer

word na die behandeling met rokende swaelsuur. Teken die struktuur van die
verbinding en skryf ‘n meganisme vir die vorming daarvan. (4)
p-Toluenesulphonic acid is formed when toluene is sulphonated at the para-position
after treatment with fuming sulfuric acid. Draw the structure of the compound and
write a mechanism for its formation. (4)

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Vraag 7 / Question 7 (33 punte / marks)

7.1 Skryf ‘n reaksievergelyking vir die bereiding van die volgende amied beginnende met
‘n karboksielsuurderivaat. (3)
Write a reaction equation for the synthesis of the following amide starting from a
carboxylic acid derivative. (3)

O
O
N
N
H
H

7.2 Skryf ‘n volledige stapsgewyse meganisme vir die volgende reaksie: (6)
Write a detailed stepwise mechanism for the following reaction: (6)
O
2 PhMgBr H3O+
18O C D

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7.3 Verbinding E hieronder is a voorloper in die sintese van verbinding F. Stel ‘n sintese
roete vir die omskakeling van verbinding E na verbinding F, voor. [Vereistes: Beide ‘n
Grignardreaksie asook −CN substitusiereaksie moet in die sintese gebruik word.] (7)
Compound E below is a precursor in the synthesis of compound F. Suggest a synthetic
route for the conversion of compound E to compound F. [Requirements: Both a
Grignard reaction and a −CN substitution reaction must be used in the synthesis.] (7)

CHO CO2H

OCH3 OCH3
OCH3 OCH3

E D

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7.4 Stel ‘n sintese voor vir verbinding H met toleen as uitgangstof. Neem aan dat
oplosmiddels en enige ander reagense beskikbaar is. Toon alle stappe volledig met
reagense en organiese produkte. Geen meganisme of stereochemie word vereis
nie. [Wenk: ‘n amiedbeskermingsstap is betrokke.] (10)
Propose a synthesis for compound H starting from toluene. Assume that solvents and
any other reagents are available. Show all steps complete with reagents and organic
products. No mechanism or stereochemistry is required. [Hint: An amide
protection step is involved.] (10)

NH2
NH2
H

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7.5 Verskaf die ontbrekende reagense en lynstrukture van die substrate en produkte in die
volgende reaksies. Een leë blokkie mag meer as een reagens/produk/stap
verteenwoordig. Geen stereochemie of meganismes word vereis nie. (7)
Provide the missing reagents and line structures of the substrates and products for the
following reactions. One empty block may represent more than one
reagent/product/step. No stereochemistry or mechanisms are required. (7)

O
OH H2 SOCl2
O Pd/C

AlCl3

OH

BF3

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EINDE / END

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