CHE 1000 Course Outline - Organic Chemistry Component - 2018-2019

THE UNIVERSITY OF ZAMBIA
DEPARTMENT OF CHEMISTRY
CHE 1000: INTRODUCTORY CHEMISTRY
COURSE OUTLINE: ORGANIC CHEMISTRY COMPONENT

2018/2019 ACADEMIC YEAR
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Specific Objectives:
At the end of the teaching of this component, the students should be able to:
(a) Draw the MO diagrams for organic molecules (methane, ethane, ethene, ethyne, allene, HCHO,
CH3CHO, H2C=C=O)
(b) recognise as well as describe types of bonds (- and - bonds; - bond as spy-spz  bond),
functional groups and types of carbon and hydrogen atoms (as sp3/sp2/sp; primary/secondary/
tertiary/quaternary and allylic/vinylic/ acetylinic) in organic compounds and explain differences
between - and -bonds.
(c) classify and name organic molecules -by IUPAC rules as well as trivial/, systematic names and
draw structures corresponding to given names.
(d) draw structural and geometrical isomers (alkenes only) and recognise isomeric relationships.
(e) describe sources hydrocarbons and predict and explain their physical properties in terms of their
molecular structure
(f) recognise types of reactions – oxidation, reduction, addition, substitution, acid-base neutralisation,
and reactive species and explain relative stabilities of radicals and carbocations.
(g) predict the products/reagents/conditions/starting materials and write mechanisms for selected
reactions of alkanes and alkenes: halogenation of alkanes, addition of hydrogen, halogens and
halogen acids to alkenes.
Course Outline
1.0 Introduction to organic chemistry

 What is organic chemistry?
 Scope, relevance and natural occurrence
 Why it has to be studied separately?
2.0 Review of bonding in organic compounds
 Brief overview of hybridisation of C, N and O and how a covalent bond is formed-

LCAO? (covered in earlier part of CHE 1000);
 M.O. diagrams/pictures for methane, ethane, ethene, ethyne, methanal, allene, ketene
 Types of C-H, C-C, C-N, C-O and C-X bonds in organic compounds: σ- and p-bonds,
description of σ-bonds as (spy-spz) and (spy-s), differences between σ- and p-bonds.
3.0 Elemental Composition and classifications of Organic Compounds
3.1 Classification based types of elements present:

 Compounds containing carbon and hydrogen only (Hydrocarbons)
 Compounds containing C, H and other elements, N,O, X (Hydrocarbon derivatives)
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3.2 Further classification of hydrocarbons:
 based on nature of carbon chain and types of C-C bonds:
(i) Aliphatic hydrocarbons: alkanes (cyclic and acyclic), alkenes (cyclic and acyclic)
and alkynes, general formulae, alkenynes, examples
(ii) Aromatic hydrocarbons: benzene, toluene and xylenes
3.3 Further classification of hydrocarbon derivatives:

 Definitions; structures, names and examples of functional groups; priority order of
functional groups, polarity and acid/base/neutral characteristics.
 classification of hydrocarbon derivatives based on functional groups: Alkyl
halides, alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, nitro
compounds, amines, amides, amino acids, Difunctional compounds.
4.0 Representation of Organic Compounds
4.1 Representation of aliphatic organic compounds

 Molecular and structural formulae,
 Representation of structural formulae- Lewis, Kekule, expanded, condensed and bond-
line (or line) structures- line structures preferred.
4.2 Representation aromatic organic compounds- limited to benzene and its derivatives:
 Benzene: molecular formula, orbital picture, Kekule structures, toluene, xylenes,
mono- and di-substituted benzenes.
4.3 Classification of carbons, hydrogens and nitrogens:

(i) primary, secondary, tertiary, quaternary
(ii) vinylic, allylic, alkynylic/acetylinic, benzylic
5.0 Nomenclature of Organic Compounds
5.1 Systems of nomenclature: trivial (common), systematic and IUPAC – scope and limitations
5.2 IUPAC system of nomenclature:

 introduction, definitions of terminology, underlying principles,
 Architecture of IUPAC nomenclature: root, prefixes and suffixes; multipliers, punctuation
marks
5.3 IUPAC nomenclature of aliphatic cyclic and acyclic organic compounds in detail
 Prefixes and suffixes for all common functional groups

 IUPAC rules for naming organic compounds in detail (all common functional groups)
 Naming cyclic and acyclic alkanes, mono-, di- and tri-functional compounds by IUPAC
rules: Liberal examples covering all common functional groups and alkenynes.
5.4 IUPAC nomenclature of aromatic compounds – benzene derivatives only
 IUPAC nomenclature rules for benzene derivatives

 Naming mono- and di- substituted benzenes:
2
6.0 Isomerism-
6.1 Definitions, terminology and classification- constitutional- and stereo-isomers
6.2 Constitutional isomers:
 Definitions, further classification, examples
 Differences in properties of structural isomers
6.3 Stereoisomerism: limited to geometrical isomerism in alkenes
 Origin, definitions and classification.
 Geometrical isomerism in alkenes: restricted rotation about double bonds,
 Nomenclature of geometrical isomers, configurational labels- Cis- and Trans-
6.4 Drawing structures for isomers corresponding to given MF:

 Index of hydrogen deficiency (IHD) or unsaturation number (UN): brief explanation,
calculation and interpretation of IHD
 Guidelines for writing structures for isomers corresponding to given MF.
7.0 Properties of Hydrocarbons

7.1 Physical properties alkanes, alkenes, alkynes, benzene: polarity, solubility, acidity-pKa, b.p.
7.2 Reactions of Aliphatic Hydrocarbons

(a) Introduction to Organic Reactions
 Definitions, terminology- substrate, reagents, solvents, reaction conditions
 Notations/conventions for writing organic reactions- different types of arrows, curly
arrows
 Types of organic reactions and examples: acid-base, oxidation, reduction, addition,
substitution, elimination, esterification reactions...
 What is involved in organic reactions?: Covalent bond cleavage-homolytic and heterolytic
 Reactive intermediates and species: radicals, carbocations and carbanions- hybridisation
state, shapes (of carbon) and relative stability; electrophiles, nucleophiles.
 Notations and conventions for writing organic reaction mechanisms
(b) Reactions of Alkanes and cycloalkanes:

 Sources of alkanes and physical properties
 Reactivity and reactions: Combustion- balanced equation, applications; Substitution
reactions: halogenation – reaction equations, conditions: thermal, photochemical,
peroxides and NBS, products- composition, Mechanism of radical halogenation of alkanes
(thermal, photochemical, peroxides and NBS), limitations and scope. Relative reactivity of
10, 20 and 30 hydrogens- regiospecificity
(c) Selected Reactions of Alkenes and Cycloalkenes:

Structure & reactivity, addition of H2 and, X2; applications HX- mechanism & applications.
RECOMMENDED TEXTBOOK
Stevens S. Zumdahl and Susan A. Zumdahl (2014), Chemistry 9th Edition, Brooks/Cole, USA
Advise: 1. Revise chapter 9: Covalent bonding done earlier (pages 415-422 and 428-430)
2. Study Chapter 22: Organic and Biological Molecules, pages 1022- 1044 and attempt questions and
exercises on pages 1071 – 1074.
3. In addition, you will need to read organic chemistry book(s) - to be advised during lectures
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THE UNIVERSITY OF ZAMBIA

CHE 1000: INTRODUCTORY CHEMISTRY

COURSE OUTLINE: ORGANIC CHEMISTRY COMPONENT

1.0 Introduction to organic chemistry

2.0 Review of bonding in organic compounds

 Brief overview of hybridisation of C, N and O and how a covalent bond is formed-

3.0 Elemental Composition and classifications of Organic Compounds

3.1 Classification based types of elements present:

3.3 Further classification of hydrocarbon derivatives:

4.0 Representation of Organic Compounds

4.1 Representation of aliphatic organic compounds

4.3 Classification of carbons, hydrogens and nitrogens:

5.0 Nomenclature of Organic Compounds

5.2 IUPAC system of nomenclature:

 Prefixes and suffixes for all common functional groups

5.4 IUPAC nomenclature of aromatic compounds – benzene derivatives only

 IUPAC nomenclature rules for benzene derivatives

6.4 Drawing structures for isomers corresponding to given MF:

7.0 Properties of Hydrocarbons

7.2 Reactions of Aliphatic Hydrocarbons

(b) Reactions of Alkanes and cycloalkanes:

(c) Selected Reactions of Alkenes and Cycloalkenes:

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