School of Chemistry, University of KwaZulu-Natal, Westville Campus

CHEM 220W
ORGANIC CHEMISTRY
2024

Course Structure
The course comprises 36 lectures, 12 tutorials, 6 laboratory practicals and 2 workshops.

The Central Teaching Office can be found on level 3, H Block, Westville Campus. There will be
course administrators there to handle all the administrative tasks of the course.

Your lecturers for the module are:

Professor Neil A. Koorbanally, Tel. 031 260 3189, [email protected]
Dr Matshawe Tukulula, Tel. 031 260 8756, [email protected]

All your lecturers have offices on level 3, H Block, Westville Campus

Your course co-ordinator is Dr Matshawe Tukulula

Textbook
The formal prescribed textbook for this course is

P.Y. Bruice, Organic Chemistry, Pearson/Prentice Hall

(Any edition will be fine. The current edition is the 8 th Edition, Global edition)

Note that this text will be used extensively in the course. It is thus essential that each student purchase
their own copy. Other organic textbooks can also be consulted.

Course Assessment
The Course Mark is made up as follows:
Class (or DP) Mark 33%, Examination 67%
The Class Mark is in turn made up as follows:
Class Tests 15%, Laboratory Practicals 18%

Class Tests
These will be communicated to you in due course. Please note that the DP requirement is 100%
attendance at tests.

Lectures (venue: Lecture theatre L09, L Block)

Attendance at lectures is compulsory and registers will be taken regularly. If you are found not to be
attending lectures, you will not be granted a DP certificate to write the final examination.

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CHEM220 course outline
Lecture Timetable

Day Period Time Venue

Monday 4-5 10.30 AM – 12.10 T7
Wednesday 2 08:40 AM – 9.25 AM T1
Thursday 7 13.15 PM – 14.00 PM T7

Laboratory Practicals
Laboratory practical sessions will be held on Monday and Friday afternoons in the Synthetic Teaching
Laboratories, 1st Floor, H Block, commencing at 2.10 pm sharp, from Monday the 20th of February.
Practical manuals must be collected from the Laboratory Technician located in the laboratory in the
1st week of lectures. Bench and locker allocations will be posted on the noticeboard outside the
laboratories; anyone not on the list should please see the laboratory technician. Practical reports must
be submitted to your demonstrator one week after the date of the practical. Late submissions will not
be accepted.

Closed leather shoes, laboratory coats and safety glasses must be worn in
all laboratory sessions

There will be NO supplementary or “make up” practicals. Students who miss practicals without
adequate explanation will be given ZERO for that session, which may cost them their DP’s (see DP
requirements). Students who are unable to attend for medical or other unavoidable reasons should
give their certificates or other supporting documentation to the Central Teaching Office as soon as
possible after returning to campus.

Laboratory Practical Exemptions

Practical exemptions may be granted to those students who are repeating a course given by this School
and who attained a sufficiently high standard of work in previous years. Students wishing to apply for
practical exemption must please see the Central Teaching Office for details on how to apply. These
applications will then be processed and you will be informed, before practicals begin, whether you
have exemption, or are required to repeat the practical course.
NB. Application for a practical exemption does not mean you are exempt. You need to attend
practicals until such time you are informed officially that you have been exempted.

It is your responsibility to ensure that you either have exemption or have been allocated a bench and
locker.

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CHEM220 course outline
 A subminimum of 40.0% for the Class Mark,
80% attendance at Laboratory Practicals,
and
100% attendance at Class Tests

are
DP requirements.

Students who fail to attend 80% of Laboratory Practicals and 100% of Class
Tests (for whatever reasons), or who fail to obtain the Class Mark subminimum
will have their DPs refused, and will NOT be allowed to sit the final examination.

Plagiarism
Plagiarism is defined as the submission or presentation of work, in any form, which is not one's own
without acknowledgement of the source(s). It is an attempt to deceive the reader that the work or ideas
presented are your own, whereas, in fact they are the words/ideas of others.

With regard to essays, reports and dissertations, a simple rule should be used when deciding if it is
necessary to acknowledge sources. If you obtain information from an outside source, that source must
be acknowledged. Another rule to follow is that any direct (verbatim) quotation must be placed in
quotation marks and your wording should clearly indicate that the item is not your own work and the
source immediately cited. The mere inclusion of the source in a bibliography shall not be considered
sufficient acknowledgement.

This applies to all work contributing to assessment, including laboratory reports and projects. All
assessed work must be your own individual effort. Copying of laboratory reports, for example, is
plagiarism. You may share data, where appropriate, but the calculations, answers to assignment
questions and the discussion of results must be your own work.

Work referred to from Internet sources must also be acknowledged as above, with the web address
(URL) of the source included and the date accessed.

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CHEM220 course outline
Structure of the module
Purpose of the module:
This module is designed to introduce organic chemical reactions and the way in which they occur, as
well as the tools used to identify the products of reactions.

Learning outcomes for the module:

Specific outcomes for each unit within the module are spelled out in each unit. In general, students
should be able to predict reactions from starting materials as well as identify possible reagents for
synthesizing target molecules. They must be able to write the mechanism of how particular organic
reactions occur. They must be able to identify simple organic compounds from common analytical
and spectroscopic tools.

Students must be able to perform an appropriate range of laboratory techniques in organic chemistry
and report on the synthesis of organic compounds, relating them to theory.

Assessment criteria:
Students must be able to demonstrate an understanding of organic chemical reactions by being able to
write mechanisms for reactions, being able to predict products and identify reagents for target
molecules in a test or examination. Students must also be able to identify simple organic compounds
using spectroscopic means.

Course Content:

Unit 1: An introduction to Nuclear Magnetic Resonance Spectroscopy (NMR) [Prof. Koorbanally]

Unit 2: Stereochemistry [Prof. Koorbanally]
Unit 3: The chemistry of aromatic compounds [Dr Tukulula]
Unit 4: Carbonyl chemistry [Dr Tukulula]
Unit 5: Substitution and elimination reactions [Dr Tukulula]
Unit 6: Reactions of Alkenes [Dr Tukulula]
* Each Unit takes approximately two weeks to cover

Read through the box on the use of curved arrows in your textbook before you start the course.

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CHEM220 course outline
 Unit 1
NMR Spectroscopy

Outcomes:
After reviewing the material covered in this section you should be able to:
● Explain the behaviour of nuclei in the presence of an applied magnetic field
● Draw out a simple diagram of an NMR spectrometer
● Understand the effects of varying field strengths
● Be able to explain diamagnetic shielding effects
● Be able to assign the number of non-equivalent signals for a given compound
● Discuss the role of a reference compound and the chemical shift of a particular signal
● Estimate the chemical shift for a particular signal using correlation tables
● Clearly understand the use of signal integrals and their importance in structural elucidation
● Explain the effect of anisotropy on a particular signal
● Be able to calculate the signal splitting for a compound as well as be able to work back from a
spectrum to determine the number of neighbouring protons
● Understand what coupling constants are and how they may be useful in determining the
structure of a compound (e.g. cis/trans isomers)
● Given a structure one should be able to predict and draw a NMR spectrum
● Given a spectrum for an unknown compound be able to elucidate a plausible structure based
on the information provided. One must also be able to critically assess your answer to check if it is
indeed plausible

Contents: Shielding, Number of non-equivalent signals, chemical shift, use of correlation tables,
integration of NMR signals, anisotropic effects, signal multiplicity (first order coupling only), coupling
constants and applications.

● Coupling in aromatic systems

● Introduction to NMR and nuclei effects
● Number of signals in the NMR spectrum
● Chemical shift
● Use of correlation tables
● Integration of NMR signals
● Anisotropic effects
● Splitting of signals (first order only!) Pascal's triangle
● Examples to illustrate the above concepts
● Coupling constants

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CHEM220 course outline
 Unit 2
Stereochemistry

Outcomes:
After reviewing the material covered in this section you should:
● Distinguish between different kinds of isomers
● Use priority rules to assign cis/trans or E/Z configuration of an alkene
● Draw the E- or Z-isomer of a given alkene
● Distinguish between mirror images that are superimposable and mirror images that are not
superimposable
● Decide whether an object is chiral or achiral
● Locate asymmetric carbons (stereocentres) in a molecule
● Define enantiomers
● Draw chiral molecules in tetrahedral form
● Draw chiral molecules in a Fischer projection
● Compare chiral molecules drawn in perspective formulas, Newman projection or in Fischer
projection
● Draw the enantiomer of a given chiral compound
● Assign priorities to substituents around a stereogenic carbon
● Apply priority rules to assign R, S-configurations to stereogenic centres
● Know what plane-polarised light is
● Define an optically-active compound
● Draw a polarimeter
● Define levorotatory or dextrarotatory
● Calculate the specific rotation of a compound
● Explain what a racemic mixture is
● Explain the concept of an ‘enantiomerically pure’ compound
● Calculate the optical purity of a mixture of enantiomers
● Calculate the enantiomeric access of a mixture of enantiomers
● Draw the different stereoisomers of a compound with more than one stereogenic centre
● Distinguish between enantiomers and diastereomers
● Draw the diastereomer of a given chiral compound
● Recognise a plane of symmetry
● Identify a meso compound
● Propose a method for the separation of two enantiomers
● Explain what ‘resolution of a racemic mixture’ is
● Understand the relationship between the physical properties of pairs of enantiomers or
diastereomers
● Understand the relationship between specific rotations of pairs of enantiomers or diastereomers
● Understand the relationship between the chemical properties of pairs of enantiomers or
diastereomers
● Understand the relationship between biological properties of pairs of enantiomers or
diastereomers
● understand the chair conformation of cyclohexane and explain equatorial and axial substituents
and associate energies with different substituents

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CHEM220 course outline
 Unit 3
Aromaticity: Reactions of Benzene and Substituted Benzenes

Outcomes:
After reviewing the material covered in this section you should:
● Know and understand the requirements for aromaticity & be able to apply them in determining
whether or not a molecule/ion is aromatic
● Explain the bonding in aromatic heterocyclic molecules
● Give the general mechanism for electrophilic aromatic substitution
● Understand:
o the role played by delocalisation in stabilising the intermediate carbocation
o why electrophilic addition does not occur
● Give the mechanism for generating each of the electrophiles involved in the 5 electrophilic
aromatic substitution reactions
● Understand why and be able to predict, what rearrangements will occur in a Friedel-Crafts
alkylation reaction and know how to prevent this occurring, using a combination of Friedel-Crafts
acylation & reduction reactions
● Know the starting materials, reaction conditions and products of the various substituent
interconversions:
o reactions of alkyl substituents
o catalytic hydrogenation of double and triple bond substituents and of benzene itself
o oxidation of alkyl substituents to aldehydes and carboxylic acids
o reduction of nitro groups to give amines on an aromatic ring
● Understand the concepts of induction and resonance & how they (de)activate an aromatic ring
toward electrophilic aromatic substitution and be able to draw resonance structures illustrating these
concepts
● Understand the classification of substituents into strong, medium and weak activators and
deactivators and know into which group each of the substituents fall
o be able to draw resonance structures for each of these classes of substituents
● Understand the principles behind the effect a substituent already present on an aromatic ring
has on further substitution, the connection between activation/deactivation and ortho & para/meta
directing groups, why the halogens are the exceptions to this, and (of course…) draw resonance
structures illustrating the above
● Understand the effect of substituents on reaction conditions
● Understand the importance that the order in which substituents are introduced onto an aromatic
ring plays in the design of a particular multi-substituted aromatic ring, and how to balance the opposing
effects of more than one substituent to predict the net effect
● Know the uses of arenediazonium salts in the syntheses of various substituted benzenes and
the mechanisms involved, and the use of these salts as nucleophiles
● Understand why nucleophilic aromatic substitution does not readily occur, know the conditions
under which it does, and the reaction conditions and mechanism involved
● Understand why the benzyne intermediate is needed to explain the experimental observations,
& how, although it cannot be isolated, its existence is supported by trapping the intermediate

Material covered in this unit:

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CHEM220 course outline
● review of 1st year/ self study
o electron delocalization & bonding in benzene
o nomenclature of monosubstituted benzenes, disubstituted & polysubstutited benzenes
o effects of substituents on pKa
● general reading
o antiaromaticity; aromaticity to molecular orbital theory; ortho-para ratio; arenediazonium ion
as electrophile; polycyclic benzenoid hydrocarbons
● definition of & criteria for aromaticity (Huckel rules)
o selected examples (hydrocarbons, cations & anions, fused systems; heterocyclic systems)
● consequences of aromaticity
o pKa
● how benzene reacts & mechanism of electrophilic aromatic substitution
o halogenation (Br, Cl, I) & nitration
o reversible sulfonation
o Friedel-Crafts alkylation; skeletal rearrangement with primary alkyl halides
o Friedel-Crafts acylation; indirect alkylation by acylation-reduction
● reactions of aromatic substituents
o oxidation & reduction reactions
● effects of aromatic substituents on reactivity & orientation of further substitution
o substituent electron donation/withdrawal by induction &/or resonance & relationship to
activating/deactivating ability; classification of substituents as weakly/moderately/strongly
activating/deactivating
● effect of substituents on orientation & relationship to activating/deactivating ability
o additional effects
● synthesis design
o monosubstituted & disubstituted benzenes
o trisubstituted benzenes, using arenediazonium salts
● nucleophilic aromatic substitution
● benzyne

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CHEM220 course outline
 Unit 4
Chemistry of Carbonyl Compounds

Outcomes:
● After reviewing the material covered in this section you should:
● Be able to identify & draw structures for the functional groups of carboxylic acids, acid
anhydrides, acyl halides, esters, amides & nitriles
● Give the general mechanism for nucleophilic acyl substitution
● Understand the relationship between the basicity of a given leaving group and:
o its leaving group ability
o the pKa of its conjugate acid
● predict, given specific pKa values
o whether or not a given substitution reaction will occur
o which acid derivatives can be substituted by others
o the products formed, should a reaction occur (use Table 16.1, and the reactions of NaCl,
NaOAc, CH3OH, H2O and CH3NH2 with each of benzoyl chloride, benzoic anhydride, methyl
benzoate, benzoic acid and benzamide as specific examples)
● give the mechanisms involved for each of the above substitution reactions
● understand:
o why 3O amines do not form amides
o why only one equivalent of amine is needed in the reaction with an ester, but two equivalents
are required in the reactions with acyl halides & anhydrides
o the differences between the mechanisms of the acid- & base-catalysed hydrolyses of esters, &
why excess water is needed in the acid hydrolysis
o why transesterification is a poor synthetic method for the synthesis of esters
o why an excess of alcohol is required when producing esters from carboxylic acids
o why a catalyst is required for amide hydrolysis
● understand
o why aldehydes/ketones do not undergo acyl substitution, but rather nucleophilic addition or
addition/substitution reactions
o what factors govern the above reactions and the role of lone pair electrons
o the differences in the mechanisms of reactions involving strong & weak nucleophiles
o the relative reactivities of aldehydes & ketones, and where they fit in in the relative reactivities
of carbonyl compounds towards nucleophiles
● give the mechanisms involved for each of the addition reactions
● understand
o why addition of a 2O amine to a ketone gives an enamine rather than a imine
o the factors governing the position of a carbonyl/gem diol equilibrium
o why the reaction of Grignard reagents with esters and acyl halides requires a 2:1 molar ratio,
and why the reaction does not work with amides and acids
o the problem involved in the reaction of LAH and esters and acyl halides, and how this can be
avoided
o the difference in the mechanism of the reaction of LAH with acids & amides, and why a 2:1
molar ratio is required

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CHEM220 course outline
Material covered in this unit:
● review of 1st year/self study
o nomenclature of acids & acid derivatives
o nomenclature of aldehydes & ketones
o carbonyl -hydrogens & their acidity; keto-enol tautomerism
● general reading
o structure of carboxylic acids & their derivatives; physical properties of carbonyl compounds;
naturally occurring acids & derivatives
● how class 1 carbonyl compounds react: nucleophilic acyl substitution
o relative reactivities of acids & their derivatives
o general mechanism
● reactions of acids & acid derivatives
o acyl halides
o acid anhydrides
o esters; acid catalysed ester hydrolysis; hydroxide ion promoted hydrolysis
o acids
o amides; acid catalysed amide hydrolysis
● synthesis design: cyclic compound synthesis
● how class 2 carbonyl compounds react: nucleophilic addition
o relative reactivities of aldehydes & ketones
● reactions of aldehydes & ketones
o with carbon nucleophiles (Grignard reagents, HCN)
o with hydride ion
o with nitrogen nucleophiles (formation of imines and enamines) with oxygen nucleophiles (addition
of H2O, ROH; use as protecting groups)
o with sulphur nucleophiles
● stereochemistry of nucleophilic addition – Re and Si faces
● synthesis design: retrosynthesis
● reactions of enols & enolate ions: carbonyl group -substitution/addition
o general mechanism of acid & base catalysed -carbon substitution
o aldol addition; mixed aldol addition; dehydration to form ,-unsaturated aldehydes/ketones §

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CHEM220 course outline
 Unit 5
Substitution and Elimination Reactions

Outcomes:
After reviewing the material covered in this section you should:
● Know how alkyl halides will react (substitution / elimination)
● Explain the mechanism (including the rate law for the reaction) of an SN2 reaction in detail
● Predict the stereochemical outcome of an SN2 reaction
● Describe the influence of the following factors on the outcome of an SN2 reaction:
o structure of substrate
o the nature of the leaving group
o reactivity of nucleophile
o effect of solvent on reactivity of the nucleophile
o influence of steric effects on nucleophilicity
o concentration of nucleophile
o the solvent in which the reaction is carried out
● Know the difference between a protic and aprotic solvent
● Predict the product if different nucleophiles are reacting with an alkyl halide or, vice versa,
decide which nucleophile to use if a given product must be prepared from a given alkyl halide
● Explain the mechanism (including the rate law for the reaction) of an SN1 reaction in detail
● Predict the stereochemical outcome of an SN1 reaction
● Describe the influence of the following factors on the outcome of an SN1 reaction:
o structure of substrate
o the nature of the leaving group
o reactivity of nucleophile
o the solvent in which the reaction is carried out
● Predict when a carbocation will rearrange and write the mechanism thereof
● Be cognisant of the increased stability of allylic and benzylic carbocations
● Be able to predict whether a specific substrate will predominantly give a SN1 or an SN2 reaction
● Explain the mechanism of an E2 reaction
● Predict the stability of an alkene
● Predict the regioselectivity of an elimination reaction and apply Zaitsev’s rule
● Be cognisant of the stereochemical implications of an E2 reaction
o (in the transition state the groups being eliminated must be in an anti-periplanar or syn-periplanar
conformation)
● Explain the mechanism of an E1 reaction, including stereochemistry and regioselectivity
● Predict whether a particular substrate will undergo an E1 or E2 reaction
● Consider the substrate and conditions of a reaction and predict what the mechanism and major
product will be (Substitution - SN1, SN2; elimination - E1 or E2)
● Apply substitution and elimination reactions to the synthesis of organic compounds

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CHEM220 course outline
 Unit 6
Reactions of Alkenes

Outcomes:
After reviewing the material covered in this section you should:
● Know how alkenes will react
● Understand the thermodynamics and kinetics of a reaction
● Describe the mechanism of addition of a hydrogen halide to an alkene
● Predict the stability of a carbocation
● Try and predict the structure of the transition state (Hammond postulate)
● Describe the mechanism of the acid-catalysed addition of water to alkenes
● Understand the rearrangement of carbocations
● Explain the addition reactions of halogens to alkenes
● Be able to perform the addition of water to an alkene without any rearrangements
● (Know the mechanism of the oxymercuration – reduction reaction)
● Be able to perform a reaction that is the equivalent of an anti-Markovnikov addition of water
to an alkene (Hydroboration/oxidation – know mechanism)
● Propose a reaction for the anti-Markovnikov addition of HBr to alkenes
● (Radical addition of HBr to alkenes – know mechanism)
● Hydrogenation of alkenes (revision of first year – self study)
● Propose a reagent for the syn-hydroxylation of alkenes (KMnO4, OsO4)
● Know how to prepare an epoxide from an alkene
● Predict the reactions of an epoxide
● Ozonolysis of alkenes (revision of first year course – self study)
● Apply the reactions of alkenes to the synthesis of organic compounds

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CHEM220 course outline