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Eötvös Loránd Science University
Faculty of Sciences
Department of Chemistry
Core (required) / Core Elective /
Free Elective Course
COURSE OUTLINES
and Prerequisites
2013
Course Title: Organic chemistry (2)
1.
Course Code
Semester
Grading
kv1c1es2
2
Colloquium
Credits / Language
Weekly
Hours
3/3
English
Major
Chemistry
BSc
2. Course Type:
Lectures
3. Course Instructor and Department:
Dénes Szabó, Institute of Chemistry, (Department of Organic Chemistry)
4. Course Instructor:
Name:
Dénes Szabó
Title:
Assistant professor
Department, Institution:
Department of Organic
Chemistry, Institute of Chemistry
5. Course Requirements:
General chemistry, Organic chemistry (1)
6. Course Prerequisites:
6.1. Prerequisites
Organic chemistry (1), kv1c1es1
6.2. Recommended
General chemistry
7. Course Objectives:
To introduce the students to the basic properties of the following groups of organic compounds: oxygen containing carbon compounds (alcohols, phenols, aldehydes, ketones, carboxylic acids, acid derivatives), nitrogen containing organic compounds (amines, amides,
nitriles, nitro compounds, diazo compounds), heteroaromatic compounds, polycyclic aro-
matic hydrocarbons, organic sulfur compounds. The aim is to interpret the physical and
chemical properties on the basis of the structure of functional groups.
8. Course Outline:
Topics Covered:
To present the groups of organic compounds by the following system: functional groups,
nomenclature, examples, electron structure, physical and chemical properties.
8.1. Course Outline (Weekly)
Add/Drop courses (Week 1);
1. lecture (Week 2)
Alcohols and phenols – Structure of alcohols and ethers, nomenclature, physical properties.
Synthesis of alcohols. Acidity and basicity. Alkylation of alcohols, Williamson synthesis.
The acylation of alcohols.
2. lecture (Week 3)
Preparation of sulfonic esters and their use in syntheses. Esters of inorganic acids.
Halogenation of alcohols. Dehydration of alcohols: preparation of ethers and alkenes.
3. lecture (Week 4)
Oxydation of alcohols. Reactivity of ethers, cleavage of ether bond. Structure and cleavage
of epoxides. Structure and acidity of phenols. Chemical transformation of phenols:
alkylation, oxydation and substitution.
4. lecture (Week 5)
Aldehydes and ketones – Nomenclature, important aldehydes and ketones. Physical
properties. General characterization of reactivity of carbonyl group. Mechanism of
nucleophilic addition. Addition reactions with O-nucleophiles.
5. lecture (Week 6)
Protection of carbonyl group, removal of protecting groups. Addition reactions with Nnucleophiles. Addition reactions with C- and S-nucleophiles. Addition of heteroconjugated
compounds. Oxydation and reduction of aldehydes and ketones.
6. lecture (Week 7)
Tautomerism of aldehydes, ketones and phenols. The reaction of -carbon atom:
halogenation and aldol-addition. The preparation and reactivity of keten.
Carboxylic acids - Structure of carboxyl group, important carboxylic acids.
7. lecture (Week 8)
Physical properties of carboxylic acids. Synthesis of carboxylic acids. The acidity of
substituted carboxylic acids. Decarboxylation of acids. Heating of dicarboxylic acids.
Preparation of acid chlorides and anhydrides.
8. lecture (Week 9)
Halogenation of -carbon atom. Reactivity of halogenated acids.
Carboxylic acid derivatives - Structure of carboxylic acid derivatives (acid chlorides,
anhydrides, esters, amides, nitriles). Important acid derivatives. Chemical properties:
characterization and order of reactivity.
9. lecture (Week 10)
Nuceophilic acyl substitution of acid derivatives: reaction with water, alcohols, amines.
Reduction reactions.
10. lecture (Week 11)
The C-H acidity of esters. Caisen condensation. Acetoacetic ester and malonester
syntheses. Derivatives of carbonic acids.
11. lecture (Week 10)
Nitrogen containing organic compounds - Structure of amines. Physical properties.
Basicity of amines, depending on structure. Preparation of amines. Hofmann-degradation
and Curtius-arrengement. Alkylation and acylation of amines.
12. lecture (Week 13)
Preparation of sulfonamides. Hinsberg-test.The protection of amino group and removal of
protecting groups. Alken synthesis by Hofmann elimination. Electrophilic substitution of
aromatic amines. Reactivity of aromatic nitro compounds. Preparation of aromatic
diazonium salts and their synthetic use. Structure of amides. Acidity and basicity of
amides. Alkylation reaction of amides.
13. lecture (Week 14)
Beckmann-rearrangement. Preparation and synthetic use of diazomethane. Reduction of
aromatic nitro compounds.
Polycyclic aromatic compounds – Structure of naphthalene, anthracene and phenanthrene.
Electrophilic aromatic substitution on polycyclic aromatic compounds, reactivity and
orientation.
14. lecture (Week 15)
Heteroaromatic compounds – Structure, important heteroaromatic compounds. Physical
properties. The acidity and basicity of pyrrol and pyridine. Electrophilic and nucleophilic
reactions. Pyridine-N-oxide. Tautomerism of heteroaromatic compounds. Nucleic acid
bases. Preparation of heteroaromatic compounds.
Organic sulfur compounds – Characterization of organic sulfur compounds. Physical and
chemical properties.
9. Remarks:
10. Requirements:
10.1. Course Work:
Only students registered in the Neptun system can attend the lectures.
Prerequisites for completion of course are listed in „ELTE Organizational and Operational Regulations”).
10.2. Exam Period
The prerequisite of oral exam is performing the written test by higher than fifty
percent.
11. Make Up Policy
According to the document of "establishment and operation of the EÖTVÖS LORÁND UNIVERSITY”.
12. Office Hours/Consultation:
According to agreement on request
13. Lecture Notes, Textbook, Resources, Recommended Reading:
List of figures:
http://szerves.chem.elte.hu/oktatas/ea/SzaboD-KemiaBSc/index.html#szerves2
Recommended reading:
Náray-Szabó Gábor, Keszei Ernő, Szabó Dénes, Szepes László: Kémia, Akadémiai Kiadó,
Budapest, 2005
T. W. Graham Solomons, Craig B. Fryhle: Organic Chemistry (seventh edition) ISBN 0-47119095-0
Bruckner Győző: Szerves Kémia I-III.
14. Learning Strategy:
Learning for the exam is based on the lectures of course.
15. Syllabus Written by (Name, Title, Department/Institution)
Dénes Szabó, Department of Organic Chemistry, Institute of Chemistry,
16. Enforcement Date:
September 1, 2014.