Study Guide CHM 215 2018_final Ver 1

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School of Physical Sciences

Department of Chemistry

CHM 215

Study Guide

Organic Chemistry
nd
for 2 Year Engineering

Revised for 2018


© Copyright Reserved
CHEMISTRY 215 (CHM 215) 1

CHM 215 (2018) TIMETABLE

2018 Monday Tuesday Wednesday Thursday Friday

05 L1 06 Prac Skills 07 L2 08 L3 09
February

12 L4 13 Prac Skills 14 Tut 1 Alkenes 15 L5 16

19 L6 20 P1A 21 L7 22 L8 23
Tut 2 Alkyl
26 L9 27 P1B 28 Halides
01 L10 02

05 L11 06 07 L12 08 L13 09

12 Test Week 13 Test Week 14 Test Week 15 Test Week 16 Test Week
March

Wednesday Tut 3 Resonance,


Public
19 Timetable; 20 P2A 21 Holiday 22 Benzene & 23
L14 Aromaticity
End Q1 P2B/ Recess
26 L15
27 Q2
28 Q2/Friday 29 Recess 30
Timetable

02 Recess 03 Recess 04 Recess 05 Recess 06 Recess


Monday Tut Test 2 on
09 Recess 10 Timetable/L16 11 Tut 3 work
12 L17 13
April

16 L18 17 18 L19 19 L20 20


Tut 4 Benzene
23 L21 24 P3A 25 reactions
26 L22 27 Public Holiday

Public
30 No lectures 01 Holiday
02 L23 03 L24 04

07 Test Week 08 Test Week 09 Test Week 10 Test Week 11 Test Week
P3B;
T5 ROH,
(Sick Tests 1
14 L25 15 & 2 after the
16 RC(O), 17 L26 18
May

R(CO)R
prac)
T6 Carboxylic
21 L27 22 Class Test 23 acids & 24 L28 25
derivatives

28 L29 29 Lectures end 30 31 01

Final Examinations: 02/06 – 23/06

Supplementary Examinations: 25/06 – 30/06

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

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 2

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

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 3

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.

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 4

Textbooks

Organic Chemistry:

1) Theory:
Organic Chemistry, by JG Smith 4th or 5th edition, McGraw-Hill, 2008, ISBN: 978-981-4581-88-2
(4th) or 978-1-259-25488-8 (5th)

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

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 5

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

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 6

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.
Pre-practical talks and practical work will be carried out in the laboratories (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 2018, may be considered for exemption from
practical sessions, if the practical component was completed satisfactorily in 2017 (≥60%).
Consult the course coordinator or lab manager to find out if your qualify for exemption 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 tutorial sessions will be used for assessment and to address any questions or theoretical
concepts on which students may require further teaching. 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.

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 7

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.

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 8

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’!

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 9

Summary of Course Structure

References
Syllabus Theme Study Theme
Smith, 5th edition
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
Self study (CHM 181):
1.2 Chemical structure
Chap 1: Par 1.7
Self study (CHM 181):
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
Self study (CHM 181):
1.5 Stereochemistry
Chap 5: Par 5.2 – 5.12C
Self study (CHM 181):
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
New (Mechanisms included):
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
New (Mechanisms included):
(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

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 10

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.

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 11

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)

After studying this syllabus theme, you should be able to do the following:
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)

After studying this syllabus theme, you should be able to do the following:
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 Markovnikov’s 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

__________________________________________________________________________________

Theme 2.3: Alkyl halides


After studying this syllabus theme, you should be able to do the following:
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

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 12

After studying this syllabus theme, you should be able to do the following:
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 (Hückel’s rule).
e) Use Hückel’s 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 (PAH’s) naphthalene
and anthracene.
__________________________________________________________________________________

Theme 2.5: Aromatic reactivity

After studying this syllabus theme, you should be able to do the following:
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.

__________________________________________________________________________________

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 13

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

After studying this syllabus theme, you should be able to do the following:
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

After studying this syllabus theme, you should be able to do the following:
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.

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 14

CHM 215 ORG CHEM LECTURE PLANNING (2018)

Study Theme Approx


# Lectures

Theme 2.2: Alkenes 2 (T1)


Reactivity, Revision CHM 181 Reactions
(Also Prep) & Polymers

Theme 2.3: Alkyl Halides 7.0 (T1)


Part 1: Naming, Structure, Prep, Reactions 2.0
Grignard as base
Part 2: Substitution 3.0
Part 3: Elimination 2.0
Part 4: Summary

Theme 2.4: Resonance, Benzene & Aromaticity 4.0 (T2)


Part 1: Resonance 1.5
Part 2: Benzene Struct & Nomenc 1.0
Part 3: Aromaticity 1.5

Theme 2.5: Reactions of Benzene 6 (T2)

Theme 2.6: Alcohols & Phenols 4 (CT1)


Part 1 (Acidity & Basicity) 1.0
Part 2 (Grignard) 2.0
Part 3 (Reductions) 1.0

Theme 2.7: Carbonyl Compounds 5 (CT1)


Th 2.7.1: Aldehydes & Ketones 1.5
Th 2.7.2: Carboxylic Acids 1.0
Th 2.7.3: Carboxylic Acid Derivatives 2.5
(Condensation Polymers)

Total 27

T = Test CT = Class Test

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 15

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 student’s 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.

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


CHEMISTRY 215 (CHM 215) 16

CHM 215 Organic Reagents Data Sheet based on ‘Organic Chemistry’, Smith

Alkylating agents (R = alkyl, phenyl, etc) Halogenating agents


 Grignard:  X2, CCl4 (X = Cl, Br)
1. RX (X = Cl, Br, I)  X2, H2O (X = Cl, Br)
2. Mg, dry ether  X2, hν
3. H2O or H3O+  NBS, aq DMSO or DMSO (aq)
 Grignard in carboxylation:  HX (X = Cl, Br, I)
1. RX (X = Cl, Br, I)  HX (X = Cl), ZnCl2
2. Mg, dry ether  PBr3, ether
3. CO2  SOCl2, pyridine
4. H3O+

Hydrating agents Dehydrating agents


 H2O, H+ or H3O+  Conc. acid, e.g. H3PO4 or H2SO4
 1. BH3, THF  POCl3, pyridine
2. H2O2, HOˉ

Hydrohalogenating agents Dehydrohalogenating agents


 HX (X = Cl, Br, I)  ROˉ or HOˉ

Oxidising agents Reducing agents


 1. OsO4 Tollens:  H2, Pd/C or PtO2
2. NaHSO3 1. Ag2O  1. NaBH 4, CH3OH
 KMnO4, H2O, HOˉ NH4OH (2. H2O or H3O+) (optional)
 1. CH3CO3H 2. H3O+  1. LiAlH4, dry ether
2. H3O+ or HOˉ 2. H2O or H3O+
 1. O3  1. DIBAL-H, -78○C
2. Zn, H2O or Me2S 2. H2O
 CrO3, H2SO4 (aq) (Jones’ reagent)
 Na2Cr2O7 or K2Cr2O7 , H2SO4 (aq) = (H2CrO4)
 PCC (C5H6N+ClCrO3ˉ), CH2Cl2

Electrophilic aromatic substitution reagents Carboxylic acid derivatization reagents


 X2, FeX3 with X = Cl, Br  PBr3, ether
 I2, CuCl2 or HNO3  SOCl2, pyridine
 HNO3 (c), H2SO4 (c)  R’OH, H2SO4 (c)
 SO3, H2SO4 (c) or H2SO4 (c)  R’OH, pyridine
 RCl, AlCl3  1. NH3 or NH2R or NHR2 2. ∆ > 100 oC
 RC(O)Cl, AlCl3  NaOH, H2O
 1. NaOH 2. R’X
Benzene side chain reactions reagents Hydrolysis reagents / Deprotection reagents
[Note: Reducing agents (see also top right)]  H3O+, ∆ or H2O, H+, ∆
 RC(O)Cl, base (specify!) or (H3CC(O))2O  H2O, HOˉ, ∆
 H2SO4 (aq), ∆ or H2SO4, steam
 Br2, hν or ∆
 NBS, hν or ROOR
 KMnO4, ∆ and 1. KMnO4, HOˉ, ∆ 2. H3O+
 1. Fe, HCl
2. HOˉ
 1. Sn, HCl
2. HOˉ
 1. SnCl2, H3O+
2. HOˉ
 Zn (Hg), HCl, ∆
 NH2NH2, HOˉ, ∆

Other reagents Other reagents


 In• or Rad•  NC¯  N3¯
 Na (s) or K (s) or NaH or NaNH2  RCO2¯  HCC:¯
 ROˉ, ROH  ROH
 HS¯ or RS¯  H2O
 HOˉ
Note: Specify symbols such as R, X, etc.!

©2018 University of Pretoria, Faculty of Natural & Agricultural Sciences


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 HC≡CH HC≡C¯
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 reëls:

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

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