Study Guide CHM 215 2017 - Final Ver 2

School of Physical Sciences
Department of Chemistry
CHM 215
Study Guide
Organic Chemistry
for 2nd Year Engineering
Revised for 2017
Copyright Reserved
CHEMISTRY 215 (CHM 215) 1
CHM 215 (2017) TIMETABLE
2017 Monday Tuesday Wednesday Thursday Friday
06 L1 07 P1 08 L2 09 L3 10
February
13 L4 14 P1 15 Tut 1 Alkenes 16 L5 17
20 L6 21 P2A 22 L7 23 L8 24
Tut 2 Alkyl
27 L9 28 P2B 01 Halides 02 L10 03
06 L11 07 P2C 08 L12 09 L13 10
13 Test Week 14 Test Week 15 Test Week 16 Test Week 17 Test Week
March
20 No Lectures 21 Public Holiday 22 L14 23 L15 24
Q2/ Tut 3
27 L16 28 End Q1/P3A 29 Resonance, 30 L17 31
Benzene &
Aromaticity
03 L18 04 P3B 05 L19 06 L20 07
10 Recess 11 Recess 12 Recess 13 Recess 14 Recess

April
17 Recess 18 Recess 19 L21 20 L22 21

Tut 4 Benzene
24 L23 25 P3C 26 reactions 27 Public Holiday 28 No Lectures
Public
01 Holiday 02 P4A 03 L24 04 L25 05
08 Test Week 09 Test Week 10 Test Week 11 Test Week 12 Test Week
T5 ROH,
RC(O),
15 L26 16 P4B 17 R(CO)R & 18 L27 19
May
Carboxylic
acids
T6 Carboxylic
22 L28 23 P4C 24 acids & 25 L29 26
derivatives
Lectures
29 L30 30 end/Class Test 31 01 02
Final Examinations: 02/06 24/06
Supplementary Examinations: 26/06 30/06
L = Lecture (50 min); Tutorial session (1h); P = Practical session (6h)
2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

INDEX
TIMETABLE................................................................................................... 1
ORGANISATIONAL COMPONENT...................... .............................................. 3
Staff contact information............................................................................................ 3

Course coordinator..................................................................................................... 3
Laboratory manager.................................................................................................... 3
Textbooks................................................................................................................. 4
Exam admission......................................................................................................... 4
Assessment............................................................................................................... 5
Contact times............................................................................................................ 5
Practical sessions....................................................................................................... 6
Tutorial sessions........................................................................................................ 6
Course Website (ClickUP)............................................................................................ 6
Absence and Medical Unfitness to Attend Formal CHM 215 Activities.... ...................... 7
STUDY COMPONENT: ORGANIC CHEMISTRY.................................................. 8
General course objectives.......................................................................................... 8

Organization of study component................................................................................ 8
Summary of course structure..................................................................................9, 10
Theme 1: Basic principles of organic compounds.......................................................... 11

Theme 2: Classes of Organic Compounds................................................................... 11
Theme 2.1: Alkanes and cycloalkanes................................................................. 11
Theme 2.2: Alkenes............................................................................................ 11
Theme 2.3: Alkyl halides..................................................................................... 11
Theme 2.4: Resonance, benzene and aromaticity.................................................. 12
Theme 2.5: Aromatic reactivity............................................................................ 12
Theme 2.6: Alcohols and phenols......................................................................... 13
Theme 2.7: Carbonyl compounds........................................................................ 13
2.7.1: Aldehydes and ketones................................................ 13
2.7.2 & 2.7.3: Carboxylic acids and derivatives.................................... 13
CHM 215 Organic chemistry lecture planning. 14
APPENDIX... 15
Requirements: exam admission; passing CM215; supplementary exams... 15
Fraud/dishonesty 15
Data sheets............................................................................................................. 16, 17

ORGANISATIONAL COMPONENT
The aim of the course is to expose Chemical Engineering students to relevant concepts in Organic
Chemistry. Practical/laboratory work will be offered as part of the module and is compulsory.
Contact us
Building
Lecturers Name & Office Telephone E-mail address Consulting
number number hours
NS-!
Dr M Nkwelo Room (012) mluleki.nkwelo@up.ac.za By appoint-
Org Chem 4-47 420-3094 ment
NS-1
Dr D Riley 4-50 (012) Darren.Riley@up.ac.za By appoint-
420-3097 ment
Laboratory Dr W Mavu-
manager so CHM 2-19 (012) Winile.mavuso@up.ac.za Office hours
420-4586
Tutor (1) Post graduate students (Practicals & Tutorials)
Tutor (2)
Tutor (3)
Tutor (4)
Course coordinator (Dr M Nkwelo)
All administrative matters will be handled by the course coordinator. Students are encouraged to
discuss any academic problems with their lecturer and arrange more formal meetings by
appointment, should this be necessary.
Laboratory Manager (Dr W Mavuso)
All matters related to practical work should be addressed to the laboratory manager.

Textbooks
Organic Chemistry:
1) Theory:
Organic Chemistry, by JG Smith, 2nd , 3rd or 4th, edition, McGraw-Hill, 2008, ISBN: 978-0-07-
128665-7 (2nd) or 9780077136345 (3rd)
2) Practical:
Small Scale Syntheses: A Laboratory Textbook of Organic Chemistry, by Murray, Zanger &
James R McKee, 1995, WCB/McGraw-Hill. ISBN: 0-697-20957-1
Permission has been obtained from the publisher of the laboratory textbook to provide copies of
relevant sections, included in the Practical Guide, to all registered CHM 215 students. The
Practical Guide will be made available shortly before the first practical.
You are strongly encouraged to consult other sources such as the WWW and previously
prescribed textbooks, for example Organic Chemistry by John McMurry, any edition,
Brooks/Cole: Pacific Grove, as well. An excellent textbook, Organic Chemistry by Clayden,
Greeves, Warren and Wothers, Oxford University Press, 2009, ISBN: 0-19-850346-6, is also
available in the reserved collection of the Academic Information Service.
Exam Admission
In accordance with regulations of the Faculty of Engineering, Building Environment and Information
Technology only students with a minimum semester mark of 40% for this module will be admitted
to the June examination.
NB: See also Appendix

Assessment
Semester Tests: During Engineering Test Weeks
Examination: According to the official 2016 UP Examination Timetable
Calculation of marks:
Semester mark: Semester test 1: 35%

Semester test 2: 35%
Practicals: 15%
Class and/or tutorial tests/assignments: 15%
Final mark: Semester mark: 50%

Exam mark: 50%
Pass requirements:
1) A sub-minimum of 40% is required for this course, i.e. students should have achieved
at least 40% in the Organic Chemistry components that contribute to the final mark (AFTER
the final exam). This means all Org Chem marks obtained in theory (including exam mark)
should add up to a minimum of 40%. This rule is not applied to the calculation of the
semester marks.
2) A minimum of 50% (pass mark) in both theoretical and practical components of the
course and a final mark 50%.
Contact times
Day Time Venue

Lectures Mondays 12:30 13:30 South Hall
Wednesdays 10:30 11:30 North Hall
Thursdays 08:30 09:30 Eng III - 6
Practicals Tuesdays 09:30 15:30 Test & pre-practical lecture 09:30, Room
3-1 (Orbital) followed by laboratory work
Lab 2-18 (Chemistry building)
Tutorials Wednesdays 10:30 11:30 North Hall

Practical Sessions
The practical component forms an integral part of the course and must be completed by all students, in
other words, attendance is compulsory. Practical sessions for all groups (A, B and C) are
scheduled for Tuesdays according to the CHM 215 Timetable included in this study guide. You will be
assigned to one of the three groups for practical sessions within the first week of the semester.
Pre-practical assignments must be completed and submitted before the start of a practical session.
Short open-book tests and pre-practical lectures will be given in Room 3-1 (Orbital), Chemistry
building and the practical work will be done in lab 2-18 (Chemistry Building).
All practicals must be completed satisfactorily (attendance of all 4 practicals, and a pass mark
of at least 50%) to gain full credit for the CHM 215 module after passing the theoretical
component.
Students, who repeat the CHM 215 module in 2016, may be considered for exemption from
practical sessions, if the practical component was completed satisfactorily in 2015 (60%).
Exemption as well as the 2015 practical marks of the candidates, who qualify, will be published during
the first week of the semester. No application forms need to be completed.
Note: Exemption from practical sessions does not imply exemption from theoretical
tests, tutorial sessions or other activities scheduled for the time period of practical
sessions.
Tutorial Sessions
The style and depth of assessment are demonstrated in the tutorial and textbook (larger number)
exercises. Remember: Practise makes perfect! Six tutorial sessions are scheduled according to the
CHM 215 Timetable included in this Study Guide. A selection of exercises (see Additional Problems)
will be available on ClickUP under Study Guides) and must be completed before the start of the
sessions. The first 15 minutes of these sessions will be used for assessment and to address any
questions or theoretical concepts on which students may require further teaching. The time left will be
spent on writing and evaluating the answers to problems. There will be a short test towards the end
of each session (last 20-25 min), as determined by the lecturer, and the marks will contribute a
maximum of 5 of the 15 Tutorial Mark (see Assessment). The class test (see CHM 215
Timetable) will contribute to the remaining 10 marks.
Course Website (ClickUP)
The CHM 215 website will be used extensively for the posting of general administrative information,
announcements, the timetable and study guide for the module (including updated versions there of) and
support material for the mastery of course content during this semester. Students are expected to
consult the website on a regular basis where important official and binding information regarding the
course will be posted.

Absence and Medical Unfitness to Attend Formal CHM 215 Activities
Students, who are absent from lectures or tutorials, bear the risk of forfeiting unannounced
class or tutorial tests, important communications and being informed of possible modifications
in the module programme. The practical work is regarded as an integral part of the course and
unfinished practical work amounts to an incomplete module that leads to failing the module.
A valid official medical certificate must support absence from tests, tutorials and practical
sessions. Supplementary (Sick) tests (not for class or tutorial tests or re-examination) will only be
granted after authorized and confirmed absence from semester tests and the final examination*. These
may be in the form of oral tests, depending on the decision of the lecturer and course coordinator. Only
one absence test (for both semester tests, covering all work), will be granted during the last
week of lectures to candidates who fulfil the criteria below.
Medical certificates covering the absence from any formal course activities (tests, tutorials, final
examination*, practical sessions, and any other formal activities) will be accepted only on condition that
the certificate clearly states that the student was both ill and medically unfit to attend the specific
activity on that particular day. This certificate (original copy) must be handed to the course
coordinator, or sent by fax to the course coordinator at fax number (012) 420-4687, within three
working days of the date of the activity (test, tutorial or practical). In the case of a faxed certificate, the
original certificate must also be shown to the course coordinator on the first day that the student returns
to the university.
*If medical unfitness prevents a candidate from writing the official examination, such a student must,
within three working days after the examination, complete the necessary application forms for a special
examination, and submit it together with a valid, original medical certificate at the Faculty Office and
also inform the course coordinator.

STUDY COMPONENT: ORGANIC CHEMISTRY
General course objectives:
To study the chemistry of the most common classes of organic compounds

To develop an understanding of the underlying principles which govern the chemical behaviour
of organic compounds in order to predict behaviour of an unknown compound
To develop the ability to design syntheses of organic compounds
Your learning activities should occur within the framework presented in the study component of this
study guide.
Organisation of module:
Course structure: The summary of the course structure on the following two pages provides an
overview of the Syllabus and Study themes that will be covered in this course.
Syllabus and study themes: Syllabus and study themes are presented in full from pages 16.
References*: Consult the summary of the course structure for references to the relevant
paragraphs in the prescribed textbook for each theme. The textbook should be used as the
primary source of information for this component of the course. Lectures will be used to
highlight key concepts, to foster the development of in-depth understanding of fundamental
principles and to demonstrate how information should be used to solve problems.
Learning goals: A number of specific study goals are presented for each syllabus theme.
Teaching will focus on these learning goals and you are advised to structure your studies
accordingly.
Exercises*: Additional problems that follow on the description of each syllabus theme, must be
completed before the start of tutorial sessions. Typical problems from the textbook should be
attempted individually or in small groups in order to ensure that newly acquired knowledge
becomes firmly embedded.
* References to relevant paragraphs and textbook problems from the 4th edition of
Smith, as well as Additional problems will soon be available on ClickUP under
Study Guides!

Summary of Course Structure
References
Syllabus Theme Study Theme
Smith, 2 , 3rd or 4th edition
nd
Self study (CHM 181):

1. Basic principles 1.1 Structure and Bonding
of Organic Chap 1: Par 1.1 - 1.4; 1.6; 1.8; 1.9; 1.10; 1.11;
Chemistry 1.12
Chap 2: Only par 2.5D
1.2 Chemical structure
Chap 1: Par 1.7
1.3 Functional groups
Chap 3: Par 3.1; 3.2
Self study (CHM 181, No mechanisms):
1.4 Oxidation and Reduction
Chap 12: Par 12.1; 12.3; 12.3C,D (Not 12.3A);
12.4; 12.7; 12.9 (See also par 9:15 - no
details); 12.10; 12.12; 12.12A,B; 12.13
New (Mechanisms included):
Chap 12: Par 12.2; 12.5; 12.5A,B; See also
Themes 2.6 & 2.7
1.5 Stereochemistry
Chap 5: Par 5.2 5.12C
2. Classes of 2.1 Alkanes and cycloalkanes
Chap 4: Par 4.1 4.5; 4.7 4.10; 4.11 (only
Organic
angle strain); 4.12 - 4.14
compounds
Self study (CHM 181, No mechanisms):
2.2 Alkenes
Chap 3: Par 3.3
Chap 6: Par 6.1 6.3; 6.10
Chap 8: Par 8.1; 8.2 B; 8.5
Chap 10: Par 10.1 10.3; 10.7* (CHM 181 &
new); 10.8; 10.9 (no energy diagrammes);
10.10 - 10.14 - 10.16; 10.18
Chap 3: Par 3.4
Chap 8: Par 8.2 A, C
Chap 10: Par 10.4
Chap 15: Par 15.1; 15.2; 15.14
Chap 30: Par 30.1 30.2 A
Self study (CHM 181) & Revision (CHM 215):
2.3 Alkyl halides
Chap: 7: Par 7.1*; 7.2*; 7.4; 7.14
Chap 9: Par 9.11; 9.11A; 9.12
Chap 10: Par 10.7*
Chap 15: Par 15.1; 15.2; 15.9
(No energy diagrammes)
Chap 6: Par 6.9 B
Chap 7: Par 7.1 - 7.3; 7.5 -7.11; 7.13; 7.17;
7.18; 7.19B
Chap 10: Par 10.17
Chap 8: Par 8.1 8.8A; 8.9; 8.11
Chap 15: Par 15.2 15.4A; 15.5; 15.6 (no
details); 15.7
Chap 20: Par 20.9; 20.9A, C

Chap 1: Par 1.5

2.4 Resonance, Benzene and
Chap 2: Par 2.5 C
Aromaticity
Chap 16: Par 16.1 16.5; 16.8
Chap 17: Par 17.1 17.3; 17.5 17.8; 17.11
(self!)
2.5 Chemistry of benzene Chap 18: Par 18.1 - 18.15; 19.11

Chap 25: Par 25.11 (only top p 977)
Self study (CHM 181) & Revision (CHM 215):
2.6 Alcohols and phenols
Chap 2: Par 2.6; 2.8
Chap 9: Par 9.1 9.3A,B; 9.4; 9.6 (preparation
of alkoxides); 9.7; 9.8; 9.8A; 9.8B (E1); 9.10;
9.11; 9.11A (SN1); 9.12; 9.12A,B
Chap 10: Par 10.7*
Chap 12: Par 12.9; 12.12
Chap 20: Par 20.9*; 20.9A*, C*
(No energy diagrammes)
New: Partially also to be covered in Theme
2.7
Chap 2: Par 2.5
Chap 9: Par 9.4
Chap 19: Par 19.3; 19.8 19.11
Chap 20: Grignard & Reduction reactions:
Par 20.1 20.4; 20.7 (carboxylic acids, esters);
20.9D; 20.10; 20.10A; 20.11; 20.13; 20.13A
(esters); 20.14A; 20.16 (only RMgX); 20.17 (not
TsCl) See also Theme 1.4
Chap 21: Par 21.7; 21.7A ; 21.8
Self study (CHM 181 & 215):
2.7 Carbonyl chemistry:
Chap 20: Par 20.9*; 20.9A*, C*
Chap 21: Par 21.6
2.7.1 Aldehydes and ketones
Chap 30: Par 30.1*
2.7.2 Carboxylic acids
New & covered already in Theme 2.6:
2.7.3 Carboxylic acid
derivatives Chap 19: Par 19.1 - 19.3*; 19.5; 19.7 - 19.11*;
(Prac 1: Read Par 19.12)
Chap 20*: 20.8; See also Theme 2.6
Chap 21: Par 21.1; 21.2; 21.3 (self!); 21.5
(self!); 21.6 - 21.8
Chap 22: 22.1; 22.2; 22.3C, D; 22.6; (self!);
22.7A, B; 22.10; 22.10A, B D (A & D no
mechanisms; B & C mechanisms included),
22.11; 22.11A, B; 22.12B (soap); 22.15; 22.16;
22.16A,B; 22.18A (only hydrolysis; no
tautomerism); Chap 30: Par 30.6 A D; (Prac
3: Par 20.9; 20.9A, C, D; 20.10; 20.10A; 20.14;
20.14A)
Notes:
Study themes 1.1-1.3, 1.5. 2.1 - No lectures!

* Applicable to more than one Theme.

Theme 1: Basic principles of Organic Chemistry (CHM 181)
After studying this syllabus theme, you should be able to do the following:
a) Describe and explain structure and bonding in organic molecules
b) Understand hybridisation and the spatial requirements of hybrid orbitals
c) Use line (skeletal) structures to present organic compounds correctly and realistically.
___________________________________________________________________________
Theme 2: Classes of Organic Compounds

Theme 2.1: Alkanes and cycloalkanes (CHM 181)
a) Name acyclic alkanes and cycloalkanes according to IUPAC rules
b) Given the IUPAC name of an alkane or cycloalkane, draw the structure of the compound
c) Given the molecular formula of an alkane or cycloalkane, draw the appropriate constitutional
(structural), conformational and geometrical isomers (cis-trans)
d) Identify functional groups in compounds by name.
___________________________________________________________________________
Theme 2.2: Alkenes (CHM 181 & CHM 215)
a) Name any alkene according to IUPAC rules, including the geometry of double bonds (cis-trans,
E/Z)
b) Given the IUPAC name of an alkene, draw the structure of the compound
c) Given the molecular formula of an alkene, draw the appropriate constitutional and geometric
isomers
d) Suggest reactions for the formation of alkenes from alcohols and alkyl halides
e) Predict the products of the reactions of alkenes and explain their formation, i e
Addition of water, hydrogen and hydrogen halides (HX)
Addition of chlorine and bromine in the absence and presence of water
Oxidation of C=C bonds by hydroxylation and cleavage (OsO4, ozone, etc)
f) Application of the reactions covered in CHM 181 & CHM 215 in synthesis
g) Revise the use and application of Markovnikovs rule based on the stabilities of carbocations
h) Know the structures of common polymers, monomers and repeating units and formulate a
radical mechanism for the formation of simple chain-growth polymers from monomer units
(New)
__________________________________________________________________________________
Theme 2.3: Alkyl halides

a) Name alkyl halides according to IUPAC rules
b) Propose reactions for the synthesis of alkyl halides and their conversion to Grignard reagents
c) Formulate a mechanism for the radical halogenation of methane
d) Discuss the polarity of the C-Mg bond and its implications
e) Understand the reasons for the competition between substitution and elimination reactions of
alkyl halides
f) Formulate SN1, SN2, E1 and E2 mechanisms
g) Predict the products of substitution and elimination reactions
h) For primary and tertiary alkyl halides predict whether substitution or elimination will take place
preferentially under specific reaction conditions
i) For secondary alkyl halides predict which product mixture will be formed.

Theme 2.4: Resonance, Benzene and Aromaticity
a) Understand resonance theory and draw resonance forms for compounds
b) Name mono-, di- and trisubstituted benzene derivatives according to IUPAC rules
c) Know and use the common names of mono-substituted benzene compounds
d) Define aromaticity and explain the concept by using specific examples (Hckels rule).
e) Use Hckels rule to identify aromatic compounds and aromatic components of compounds
(including cations, anions and heterocyclic compounds).
f) Recognise and draw structures for the polycyclic aromatic hydrocarbons (PAHs) naphthalene
and anthracene.
__________________________________________________________________________________
Theme 2.5: Aromatic reactivity
a) Formulate mechanisms for the different electrophilic aromatic substitution reactions, i.e.
bromination, chlorination, sulfonation, nitration and Friedel-Crafts reactions
b) Predict the products of electrophilic aromatic substitution reactions
c) Describe the scope and limitations of Friedel-Crafts alkylation and explain the solutions that are
available
d) Understand the activation and directing effects of substituents on aromatic rings
e) Use resonance structures, as well as induction and resonance arguments, to predict the
orientation and reactivity of aromatic substitution reactions
f) Propose synthetic pathways for di- and tri-substituted benzene derivatives
g) Know and use side-chain reactions of benzene compounds in synthetic strategy.
General remarks:
Assure that nitration follows AFTER Friedel-Crafts reactions, since the ring is sufficiently deactivated by
the nitro-group that the Friedel-Crafts reaction will not take place.
The amino group is such a strong activator that it has to be modified to prevent multiple substitution in
the following step. This is achieved by conversion to the N-acetyl group, since the acetyl group can
later be removed with base.
Both Friedel-Crafts alkylation and acylation can be considered for substitution of benzene rings with
alkyl groups. However, unbranched alkyl substituents can only be obtained via Friedel-Crafts
acylation, since carbocation rearrangements will lead to the formation of branched side-chains.
__________________________________________________________________________________

Theme 2.6: Alcohols and phenols
After studying this syllabus theme you should be able to do the following:
a) Name simple alcohols and phenols, including compounds with two other functional groups (e.g.
double bond and halogen or nitro group)
b) Know and understand the properties of alcohols and phenols (hydrogen bonding, acidity and
basicity)
c) Propose reactions for the synthesis of alcohols
from alkenes (CHM 181)
by reduction of carbonyl compounds
using Grignard reagents
d) Give the products formed in the reactions of alcohols (elimination, substitution and oxidation)
e) Use the reactions of alcohols in synthetic planning
f) Formulate mechanisms for the acid-catalysed dehydration of tertiary alcohols and the
conversion of tertiary alcohols to alkyl halides with HBr and HCl (CHM 181)
g) Propose reactions for the synthesis of phenol from cumene and benzene
__________________________________________________________________________________
Theme 2.7: Carbonyl compounds
2.7.1 Aldehydes and ketones
a) Name simple aldehydes and ketones, including compounds with two other functional groups
b) Propose methods for the preparation of aldehydes and ketones by oxidation and of aromatic
ketones by Friedel-Crafts alkylation
c) Suggest reagents and define products of reduction of aldehydes and ketones
d) Explain the difference in reactivity of aldehydes and ketones towards nucleophilic addition
e) Formulate mechanisms for nucleophilic addition reactions
f) Apply addition reactions of Grignard reagents with aldehydes and ketones for C-C bond
formation.
__________________________________________________________________________________
2.7.2 & 2.7.3: Carboxylic acids and derivatives
a) Name simple carboxylic acids or derivatives, including compounds with two other functional
groups
b) Explain the physical properties of carboxylic acids
c) Understand the effect of a range of substituents on the acid strength of carboxylic acids
d) Propose reactions for the synthesis of carboxylic acids and their derivatives
e) Explain the relative reactivity of carboxylic acid derivatives and its consequences
f) Formulate a general mechanism for acyl substitution reactions and apply it to any of the
reactions of carboxylic acid derivatives
g) Formulate mechanisms for Fischer esterification, saponification and acid-catalysed hydrolysis of
esters
h) Predict the products of reactions of
Esters
Amides
i) Use nucleophylic acyl substitution reactions in synthesis
j) Provide the structure of a commercial polyester (Dacron), polyamide (Nylon) and polycarbonate
and identify the monomers from which it was obtained.

CHM215ORGCHEMLECTUREPLANNING(2016)

StudyTheme Approx
#Lectures

Theme2.2:Alkenes 2(T1)
Reactivity,RevisionCHM181Reactions
(AlsoPrep)&Polymers

Theme2.3:AlkylHalides 7.0(T1)
Part1:Naming,Structure,Prep,Reactions 2.0
Grignardasbase
Part2:Substitution 3.0
Part3:Elimination 2.0
Part4:Summary

Theme2.4:Resonance,Benzene&Aromaticity 4.0(T2)
Part1:Resonance 1.5
Part2:BenzeneStruct&Nomenc 1.0
Part3:Aromaticity 1.5

Theme2.5:ReactionsofBenzene 6(T2)
Theme2.6:Alcohols&Phenols 4(CT1)
Part1(Acidity&Basicity) 1.0
Part2(Grignard) 2.0
Part3(Reductions) 1.0

Theme2.7:CarbonylCompounds 5(CT1)
Th2.7.1:Aldehydes&Ketones 1.5
Th2.7.2:CarboxylicAcids 1.0
Th2.7.3:CarboxylicAcidDerivatives 2.5
(CondensationPolymers)
Total 27

T=Test CT=ClassTest

Appendix:
Exam admission requirements

Minimum semester mark: 30% for CHM 171 and 40% for CHM 172, CHM 215 and CHM 226
Candidates must also comply with any additional requirements unique to each module (e.g.
practical work)
Pass requirements
Final mark 50%, minimum exam mark 40%, prac mark 50% (CHM 215)
Subminimum performance for course components (e.g. CHM 215) as stated in course guide
Final marks of 49% and 74% must be re-evaluated by both internal and external examiners for
possible upward adjustment.
Supplementary examinations are awarded for CHM 100 and CHM 200 candidates with
Final mark between 45% and 49%
Final mark between 40% and 44%, if either the semester mark or exam mark was 50%
Final mark 50%, but subminimum requirements were not met.
Fraud the consequences of fraudulent activity (copying during tests and/or exams, alteration
of marked scripts etc.)
Fraud or dishonesty is a very serious matter that requires every students attention because if a
student is found guilty of misconduct, various penalties may apply such as:
denying a student, the right or privilege to register for a particular module, or revoke a credit
obtained in a module;
permanent expulsion of a student from the University etc.

CHM215OrganicReagentsDataSheetbasedonOrganicChemistry,Smith
Alkylatingagents(R=alkyl,phenyl,etc) Halogenatingagents
Grignard: X2,CCl4(X=Cl,Br)
1.RX(X=Cl,Br,I) X2,H2O(X=Cl,Br)
2.Mg,dryether X2,h
3.H2OorH3O+ NBS,aqDMSOorDMSO(aq)
Grignardincarboxylation: HX(X=Cl,Br,I)
1.RX(X=Cl,Br,I) HX(X=Cl),ZnCl2
2.Mg,dryether PBr3,ether
3.CO2 SOCl2,pyridine
4.H3O+
Hydratingagents Dehydratingagents
H2O,H+orH3O+ Conc.acid,e.g.H3PO4orH2SO4
1.BH3,THF POCl3,pyridine
2.H2O2,HO
Hydrohalogenatingagents Dehydrohalogenatingagents
HX(X=Cl,Br,I) ROorHO
Oxidisingagents Reducingagents
1.OsO4Tollens: H2,Pd/CorPtO2
2.NaHSO31.Ag2O 1.NaBH4,CH3OH
KMnO4,H2O,HONH4OH (2.H2OorH3O+)(optional)
1.CH3CO3H2.H3O+ 1.LiAlH4,dryether
2.H3O+orHO 2.H2OorH3O+
1.O3 1.DIBALH,78C
2.Zn,H2OorMe2S 2.H2O
CrO3,H2SO4(aq)(Jonesreagent)
Na2Cr2O7orK2Cr2O7,H2SO4(aq)=(H2CrO4)
PCC(C5H6N+ClCrO3),CH2Cl2
Electrophilicaromaticsubstitutionreagents Carboxylicacidderivatizationreagents
X2,FeX3withX=Cl,Br PBr3,ether
I2,CuCl2orHNO3 SOCl2,pyridine
HNO3(c),H2SO4(c) ROH,H2SO4(c)
SO3,H2SO4(c)orH2SO4(c) ROH,pyridine
RCl,AlCl3 1.NH3orNH2RorNHR22.>100oC
RC(O)Cl,AlCl3 NaOH,H2O
1.NaOH2.RX
Benzenesidechainreactionsreagents Hydrolysisreagents/Deprotectionreagents
[Note:Reducingagents(seealsotopright)] H3O+,orH2O,H+,
RC(O)Cl,base(specify!)or(H3CC(O))2O H2O,HO,
H2SO4(aq),orH2SO4,steam
Br2,hor
NBS,horROOR
KMnO4,and1.KMnO4,HO,2.H3O+
1.Fe,HCl
2.HO
1.Sn,HCl
2.HO
1.SnCl2,H3O+
2.HO
Zn(Hg),HCl,
NH2NH2,HO,
Otherreagents Otherreagents
InorRad NC N3
Na(s)orK(s)orNaHorNaNH2 RCO2 HCC:
RO,ROH ROH
HSorRS H2O
HO
Note:SpecifysymbolssuchasR,X,etc.!

pKa Acid Conjugate base Example
Suur Gekonjugeerde Voorbeeld
basis
-10 HI I
-9 HBr Br
7 HCl Cl
7 RSH2+ RSH
2 H3O+ H2O
1.4 HNO3 NO3
3.2 HF F
4-5 RCO2H RCO2
5.3 C5H5NH+ C5H5N pyridine
6 H2CO3 HCO3 NaHCO3
7 PhSH PhS
9.2 HCN CN NaCN or KCN
9.3 NH4+ NH3 NH3
9.9 PhOH PhO
10.3 HCO3 CO32 Na2CO3 or K2CO3
10.8 CH3CH2NH3+ CH3CH2NH2
11 RSH RS
15.7 H2O HO NaOH or KOH
16 ROH RO NaOEt or NaOMe
18 tBuOH tBuO tBuOK
25 HCCH HCC
35 H2 H NaH or KH
38 NH3 NH2 NaNH2
40 PhCH3 PhCH2
43 Ph-H Ph
45 CH2=CH2 CH2=CH
50 CH4 CH3 CH3MgBr
Functional groups in order of decreasing priority according to IUPAC rules:

Funksionele groepe in afnemende prioriteitsorde volgens IUPAC rels:
H C N O F Cl Br I carboxylic acid > carboxylic acid derivative>aldehyde>ketone>alcohol>phenol>thiol>

Elektronegatiwiteit amine>alkene>alkyne>alkane>>ether; halide; nitro; sulfide
2.2 2.6 3.0 3.4 4.0 3.2 3.0 2.7
Electronegativity
karboksielsuur > karboksielsuurderivaat>aldehied>ketoon>alkohol>fenol>tiol>
amien>alkeen>alkyn>alkaan>>eter; halied; nitro; sulfied

Study Guide CHM 215 2017 - Final Ver 2

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Study Guide CHM 215 2017 - Final Ver 2

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School of Physical Sciences

CHM 215 (2017) TIMETABLE

2017 Monday Tuesday Wednesday Thursday Friday

06 L11 07 P2C 08 L12 09 L13 10

20 No Lectures 21 Public Holiday 22 L14 23 L15 24

03 L18 04 P3B 05 L19 06 L20 07

10 Recess 11 Recess 12 Recess 13 Recess 14 Recess

17 Recess 18 Recess 19 L21 20 L22 21

Final Examinations: 02/06 24/06

Supplementary Examinations: 26/06 30/06

L = Lecture (50 min); Tutorial session (1h); P = Practical session (6h)

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

ORGANISATIONAL COMPONENT...................... .............................................. 3

Staff contact information............................................................................................ 3

STUDY COMPONENT: ORGANIC CHEMISTRY.................................................. 8

General course objectives.......................................................................................... 8

Theme 1: Basic principles of organic compounds.......................................................... 11

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Course coordinator (Dr M Nkwelo)

Laboratory Manager (Dr W Mavuso)

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

NB: See also Appendix

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Semester mark: Semester test 1: 35%

Final mark: Semester mark: 50%

Day Time Venue

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Course Website (ClickUP)

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Absence and Medical Unfitness to Attend Formal CHM 215 Activities

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

STUDY COMPONENT: ORGANIC CHEMISTRY

General course objectives:

To study the chemistry of the most common classes of organic compounds

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Summary of Course Structure

Self study (CHM 181):

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Chap 1: Par 1.5

2.5 Chemistry of benzene Chap 18: Par 18.1 - 18.15; 19.11

Study themes 1.1-1.3, 1.5. 2.1 - No lectures!

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Theme 1: Basic principles of Organic Chemistry (CHM 181)

Theme 2: Classes of Organic Compounds

Theme 2.2: Alkenes (CHM 181 & CHM 215)

Theme 2.3: Alkyl halides

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Theme 2.4: Resonance, Benzene and Aromaticity

Theme 2.5: Aromatic reactivity

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Theme 2.6: Alcohols and phenols

Theme 2.7: Carbonyl compounds

2.7.1 Aldehydes and ketones

2.7.2 & 2.7.3: Carboxylic acids and derivatives

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Exam admission requirements

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

2017 University of Pretoria, Faculty of Natural & Agricultural Sciences

Functional groups in order of decreasing priority according to IUPAC rules:

H C N O F Cl Br I carboxylic acid > carboxylic acid derivative>aldehyde>ketone>alcohol>phenol>thiol>

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