EDEN UNIVERSITY

School of Natural Sciences

Course Title: Organic Chemistry I

Course Code: CHE 2310

Course Aim:
To provide students with a firm foundation in organic chemistry. The course covers optical,
stereo and conformational isomerism including their application in synthesis of simple
organic compounds. It also gives an in-sight into mechanisms and stereochemistry of
substitution and elimination reactions including the oxidation and reduction of aliphatic
hydrocarbons

Course Objective:
On completion of the course, the students should be able to (TSSBAT):
1. Identify and state isomeric relationships between organic compounds using R/S
nomenclature and draw projection formulae and conformational
structures for simple organic molecules.
2. (Distinguish different types of organic reactions and explain mechanisms of
reactions for electrophilic addition, nucleophilic substitution, selected
oxidation and reduction reactions, and cleavage of ethers and epoxides.
3. Predict the products, including pertinent stereochemistry, of simple organic
reactions and provide detailed reaction mechanisms.
4. Map routes of up to 4 steps for organic synthesis and transformations.

Course Contents:

1. Course content Stereoisomerism

• Concept, definitions, general conditions for chirality, tests for chirality, biological
importance, methods of representing stereo chemical structures, projection formulae.
• Nomenclature of chiral molecules with one and more than one chiral centres, the
Cahn Ingold-Prelog system, E/Z-system for alkenes, isomer number.
• Stereoisomeric relationships: enantiomers, diastereomers, meso structures illustrated
with examples.
• Optical activity, measurement [α]D, computation of enantiomeric excess, racemates
and meso forms.

2. Conformational analysis
• Concept and definitions of terminology
• Conformational isomers and conformational analysis
i. Alicyclic compounds, sawhorse and Newman projection formulae
ii. Three to six membered monocyclic compounds, boat and chair conformers,
angle strain, torsional strain.
3. Alkenes
• Review of nomenclature, physical properties, relative stabilities Reactions including
mechanisms and applications
i. Addition reactions, including reaction mechanisms, region-specificity and
stereochemistry
▪ Addition of unsymmetrical reagents of type A-B; carbocation
rearrangements, addition of hydrogen halides, Markocnikov’s rule,
peroxide effect.
▪ Hydration: sulphuric acid and water, hydroboration-oxidation,
oxymercuration -demercuration
▪ Hydroxylation: formation of 1,2-diols, halohydrin formation

ii. Oxidation: peroxy-acids, permanganate oxidation, ozonolysis

• Structure elucidation of alkenes by oxidative cleavage

• Laboratory tests: decolourisation of bromine and cold permanganate solutions,
limitations.
• Applications: organic synthesis of alcohols, alkyl halides, epoxides, halohydrins,
diols.

4. Alkynes
• Review of nomenclature, physical properties, acidity of terminal alkynes
• Reactions:
i. Addition reactions, mechanism of hydration
ii. Oxidation: permanganate oxidation, ozonolysis
iii. Reduction to alkanes, partial stereo-specific reduction to cis- and
transalkenes, mechanism of dissolving metal reduction

• Laboratory tests: decolourisation of bromine and cold permanganate solutions,

limitations.
• Applications in organic synthesis

5. Alkyl halides

• Physical properties
• Methods of preparation and their reaction mechanisms; from alkanes and alkenes,
limitations, from alcohols.
• Reactions including mechanisms:
i. Nucleophilic aliphatic substitution, (SN), reactions:
Definition of terminology, types and classification of nucleophiles
and leaving groups, SN1and SN2 types including stereochemistry, role
of solvent, factors affecting rates of SN1and SN2, substrate structure,
 nucleophilicity, solvent polarity, steric factors, carbocationic
rearrangement and racemisation in SN1.

ii. Elimination reactions

• Terminology used in elimination reactions
• Types and strength of bases
• Dehydrohalogenation, The Zatsev’s rule, E1 and E2, stereochemistry, role of
solvent
• The Hoffmann elimination
• Factors affecting E1 and E2: substrate structure, strength of base, solvent
polarity, steric factors.

iii. Reactions with strong electropositive metals

• Grignard reagents and application in organic synthesis

6. Preparation of aliphatic hydrocarbons

• Alkenes: By 1,2-elimination reactions, dehydrohalogenation, dehydration of
alcohols
• Alkynes: Dehydrohalogenation of vicinal and germinal dihalides

7. Alcohols – The monohydrics

• Review of nomenclature, structure and classification, physical properties, acidity.
• Methods of preparation and their reaction mechanisms, regiospecificity and
stereochemistry
• Hydration, hydroxylation, Grignard synthesis of alcohols.
• Reactions and their mechanisms:
➢ Reaction due to acidity of alcohols, formation of alkoxides,
Williamson synthesis
➢ Reactions with HX, PX3, SOCl3
➢ Oxidation of alcohols: permanganate and chromate
oxidations, limitations, oxidation with PCC and Jones
reagents.
➢ Protection and deprotection of alcohol group – Benzyl,
THP, TMS and TBDMS ethers, application in organic
synthesis
➢ Simple laboratory tests for detection of alcohol group.

8. Ethers
• Review of structure and nomenclature, classification, physical properties
• Methods of preparation and their reaction mechanisms, regiospecificity and
stereochemistry
• Open chain ethers by Williamson synthesis, alkoxy-mercuration-
demercuration
• Oxiranes via halohydrins and epoxidation of alkenes
• Cleavage of open chain ethers and epoxides by acids and bases,
Assessment:

Continous Assessment (tests, assignments, tutorial quizzes, laboratory work) = 40%

Theory test 15%

Practical test 10%
Assignments/tutorial quizzes 5%
Laboratory work 10%

Final Theory Examination 60%

Prescribed Readings:

1. Organic Chemistry; T. W. Graham Solomons, John Wiley and Sons, New York,

Recommended Readings:

1. Organic Chemistry; R. T. Morrison and R.N. Boyd, Allyn and Bacon, Inc., London,
Title: Organic Chemistry II
Course Code: CHE 2320

Course Aim:

The course provides an in-depth understanding of reactions and reaction mechanisms of

carbonyl compounds, carboxylic acids and their derivatives and aliphatic amines. It covers
the principles and concepts of aromaticity and methods of preparing aromatic compounds
possessing medicinal properties.

Course Objective:
On completion of the course, students should be able to:

1. Differentiate between conjugated and non-conjugated multiple bond systems

and account for differences in addition and substitution reactions.

2. Explain reaction mechanisms of methods of synthesis of carbonyl compounds

including reaction mechanisms of carboxylic acids and their derivatives,
aliphatic amines and aromatic hydrocarbons.

3. Predict the products and explain reactions of benzene and substituted

benzenes.

4. Provide synthetic plans of synthesis of selected simple organic compounds

possessing pharmacological properties.

Course Contents:
1. Conjugated unsaturated systems
(a) Allylic system, conjugatation, orbital picture and stability of allyl cation,
radical and anion, acidity of allylic hydrogens, generation and reactions
of allyl anions
(b) Dienes, resonance stability, 1,2- and 1,4-additions and Diels-Alder
reaction.

2. Aromatic hydrocarbons
(a) Aromaticity, orbital picture, structure, conditions for aromaticity and its
prediction, and Hückel models.
(b) A survey of benzenoid aromatic systems; naphthalene, anthracene
and phenantrene; nonbenzenoid aromatic systems including
nomenclature, structures of azulene and ferrocene.
(c) Reactions:
i. Electrophilic aromatic substitution in benzene and reaction mechanisms –
sulfonation, nitration, halogenation and Friedel-Craft alkylation and
acylation
 ii. Orientation and reactivities of mono- and di-substituted benzenes towards
electrophilic substitution.

3. Carbonyl compounds
(a) Classification and nomenclature, structure and physical properties,
acidity of hydrogens.
(b) Preparation of aldehydes and ketones from alcohols and ozonolysis of
alkenes.
(c) Reactions:
i. Nucleophilic addition: Addition of sodium metabisulphite, hydrogen
cyanide, alcohols, actal/ketal and hemiacetal/hemiketal formation, Grignard
reagents
ii. Condensation: With nitrogenous nucleophile- ammonia, amines, hydrazine,
phenyl hydrazine, 2,4-dinitrophenylhydrazine and hydroxylamine. iii.
Aldol: Basicity and acidity of hydrogens of carbonyl compounds,
reaction mechanism. Use of nitromethane and allyl nitriles in aldol
reactions.
iv. Dieckmann and Cannizaro reactions
v. Oxidation: Simple laboratory tests for detection of carbonyl group and
distinction between aldehydes and ketones, protection and deprotection of
carbonyl group.
vi. Reduction: Hydrogenation, metal hydrides, Clemmensen and Wolf-Kishner
reductions

(d) Unsaturated carbonyl compounds: Michael addition and

Robinson annulations.

4. Carboxylic acids
(a) Classification, nomenclature, physical properties, acidity, substituent
effects on acidity.
(b) Preparation of carboxylic acids.
Oxidation of alcohols, carboxylation of Grignard reagents, hydrolysis of
esters, nitriles and amides.
(c) Reactions and their mechanisms
Esterification, reaction with PX3, SOCl2, Ammonia, HVZ reaction,
dehydration.

5. Acid derivatives

(a) Esters
• Nomenclature, ester formation reactions and trans-esterification
• Mechanisms of acid and base catalysed hydrolysis, reaction with Grignard
reagents, Claisen condensation, reduction to aldehydes and alcohols

(b) Amides
• Nomenclature, formation, hydrolysis and reaction with Grignard reagents
 (c) Acid chlorides
• Nomenclature
• Reactions; formation of aldehydes, esters, anhydrides

6. Aliphatic amines
(a) Nomenclature, physical properties, basicity, substituent effects on basicity, inversion.
(b) Preparation:
Ammonolysis of halides, reductive amination, reduction of nitriles, Gabriel
synthesis, Hoffmann, Lossen and Curtius rearrangements
(c) Reactions
Amines as nucleophiles, as bases, exhaustive alkylation, Hoffmann
elimination, conversion to amides, sulphonamides as Hinsberg test for
amines
(d) Enamine
• Formation
• Reactions; alkylation and
acylation

Assessment:

Continous Assessment (tests, assignments, tutorial quizzes, laboratory work) = 40%

Theory test 15%
Practical test 10%
Assignments/tutorial quizzes 5%
Laboratory work 10%

Final Theory Examination 60%

Prescribed Readings:

1. Organic Chemistry; T. W. Graham Solomons, John Wiley and Sons, New York,

Recommended Readings:
1. Organic Chemistry; R. T. Morrison and R.N. Boyd, Allyn and Bacon, Inc.,
London,