COURSE OBJECTIVE:
To present the basic principles of modern organic chemistry and its application in industry and to acquaint students with the understanding of the relationship between the structure and action of organic compounds. As part of laboratory exercises, the synthesis of basic types of organic compounds is envisaged.
COURSE IMPLEMENTATION PROGRAM:
1. Dieni, polieni: resonance
2. Aromatic compounds: properties and reactions, polycyclic aromatic compounds
3. Reactions of aromatic compounds: Basic mechanistic principle of electrophilic aromatic substitutions which include reactions of halogenation, nitration, sulfonation, alkylation and Friedel-Crafts acylation; understanding the influence of substituents on reactivity and directivity (regioselectivity) in the resulting products.3. Conjugated unsaturated systems: reactivity of compounds in terms of allyl substitution that takes place through the formation of allyl radical intermediate and explanation of its stability by molecular-orbital and resonance theory; applying said reaction in allyl bromination, understanding the stability of conjugated 1,3-butadienes by delocalization (electron resonance); understanding the principles of electrophilic 1,2- and 1,4-additions to conjugated dienes (kinetic and thermodynamic control of these reactions) as well as the stereochemical course of 1,4-cycloaddition reactions of dienes and dienophiles (Diels-Alder reactions).
5. Aldehydes and ketones I Nucleophilic addition to a carbonyl group: synthesis of aldehydes by reduction of starting acid chlorides, esters or nitriles; synthesis of ketones from starting alkynes; secondary alcohols or nitriles; the mechanism of acid-catalyzed addition of nucleophiles to the carbonyl group of an aldehyde or ketone; mechanism of hemiacetal and acetal formation; the use of acetals as protecting groups in multistage syntheses; addition reactions of primary and secondary amines to aldehydes and ketones; mechanism of hydrogen cyanide addition to the carbonyl group.
6. Aldehydes and ketones II. Aldol reactions: chemical reactivity of hydrogen atoms in the alfa-position of the carbonyl group and keto-enol tautomerism; enolate anion reaction; the mechanism of acid and base catalyzed enolization; the mechanism of acid and base catalyzed halogenation reactions of aldehydes and ketones; aldol reaction and its synthetic application;
7.-8. Carboxylic acids and their derivatives: structures and chemical reactivities of carboxylic acids and their derivatives: chlorides, anhydrides, esters (lactones), amides (lactams) and nitriles; carboxylic acid synthesis method; synthesis of carboxylic acid derivatives by intercoversion of functional groups in acyl chloride and the mechanistic principle of nucleophilic elimination reaction on acyl group.
9. Syntheses and reactions of beta-dicarbonyl compounds. chemistry of enolate anions: Synthesis of beta-ketoesters by Claisen condensation and the mechanism of nucleophilic addition and elimination of this reaction; synthesis of malonic acid derivatives by Knoevenagel reaction and Michael addition as well as the mechanism of said reactions; Mannich reaction and its mechanism;
10. Phenols and aryl halides: structure, acidity and terminology of phenols; methods of laboratory synthesis of phenol (eg hydrolysis of aryl-diazonium salts), industrial synthesis of phenol (basic hydrolysis of chlorobenzene-nucleophilic aromatic substitution); the use of phenol in Williams ether synthesis, Kolbe synthesis of acetyl-salicylic acid (aspirin); Claisen rearrangement of allyl-phenyl ether; nucleophilic aromatic substitution-addition-elimination mechanism;
11. Colloquium
7.-8. Carboxylic acids and their derivatives: structures and chemical reactivities of carboxylic acids and their derivatives: chlorides, anhydrides, esters (lactones), amides (lactams) and nitriles; carboxylic acid synthesis method; synthesis of carboxylic acid derivatives by intercoversion of functional groups in acyl chloride and the mechanistic principle of nucleophilic elimination reaction on acyl group.
9. Syntheses and reactions of beta-dicarbonyl compounds. chemistry of enolate anions: Synthesis of beta-ketoesters by Claisen condensation and the mechanism of nucleophilic addition and elimination of this reaction; synthesis of malonic acid derivatives by Knoevenagel reaction and Michael addition as well as the mechanism of said reactions; Mannich reaction and its mechanism;
10. Phenols and aryl halides: structure, acidity and terminology of phenols; methods of laboratory synthesis of phenol (eg hydrolysis of aryl-diazonium salts), industrial synthesis of phenol (basic hydrolysis of chlorobenzene-nucleophilic aromatic substitution); the use of phenol in Williams ether synthesis, Kolbe synthesis of acetyl-salicylic acid (aspirin); Claisen rearrangement of allyl-phenyl ether; nucleophilic aromatic substitution-addition-elimination mechanism;
11. Colloquium
12. Amines and related compounds with nitrogen: trigonal pyramidal structure of amines and structures of primary, secondary and tertiary amines and know their terminology; to denote the structures of aryl-amines, basic heterocyclic amines and biologically significant amines (derivatives of 2-phenylethylamine, vitamins B6 and B1, histamine); to know the principles of amine synthesis. alkylation of ammonia, Gabriel synthesis, reductive amination of aldehydes or ketones, reduction of nitriles, oximes or amides, and Hoffmann and Curtius amide rearrangements; reactions to which amines are subject: acid-base reactions, alkylation reactions, electrophilic aromatic substitutions, amine diazotations; synthesis of aryl-diazonium salts used for the preparation of benzene derivatives (Sandmeyer reaction, diazocopulation reactions).
13. Heterocyclic compounds
14. Amino acids and proteins: structures of essential amino acids and understanding their role as building blocks in protein synthesis; amino acid synthesis: enantioselective synthesis and separation of racemic mixtures of amino acids; primary and secondary polypeptide and amide bond structures; polypeptide (protein) synthesis method.
15. Colloquium II;
DEVELOPMENT OF GENERAL AND SPECIFIC COMPETENCIES OF STUDENTS:
Students who successfully complete this course will be trained to:
- recognition and use of dictionaries of organic chemistry
- drawing correct structural representations of organic molecules
- writing acceptable transformations and mechanisms for aromatic, carbonyl and heterocyclic compounds
- use of knowledge from stereochemistry in analyzing mechanisms in organic chemistry
- work in the Practicum of Organic Chemistry: for isolation, purification and identification of organic products.
STUDENTS 'TEACHING OBLIGATIONS AND THEIR PERFORMANCE:
It is obligatory to attend lectures and laboratory exercises in the Practicum of Organic Chemistry.
CONDITIONS FOR OBTAINING A SIGNATURE:
Regular class attendance and completed laboratory exercises
TEACHING METHODS:
Lectures and laboratory exercises
METHOD OF EXAMINATION OF KNOWLEDGE AND EXAMINATION:
Continuous assessment of knowledge through colloquia; written and oral exam if the student does not pass the colloquia or wants a better grade
METHOD OF MONITORING THE QUALITY AND PERFORMANCE OF COURSES:
Student survey
METHODOLOGICAL PREREQUISITES:
Courses taken: General Chemistry, Inorganic Chemistry, Organic Chemistry I
Course learning outcomes:
1. recognize and use a dictionary of organic chemistry
2. draw correct structural representations of organic molecules according to functional groups
3. use knowledge of stereochemistry when analyzing mechanisms in organic chemistry
4. write acceptable transformations and reaction mechanisms for aromatic, carbonyl and heterocyclic compounds
5. compare the reactivities of individual groups of organic compounds depending on the functional group and reaction conditions
6 to suggest the most probable reaction pathway for new molecules not given as examples in class
7. perform standard preparative procedures used to obtain simple organic compounds
Program-level learning outcomes:
1. apply standard laboratory procedures and instrumentation for preparative or analytical purposes, for organic and inorganic systems
2. interpret the results of laboratory observations and measurements, their significance and connection with the relevant theory
3. solve qualitative and quantitative problems by applying appropriate chemical principles and theories
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Organska kemija, L. G. Wade, ml., Organska kemija, prijevod 7. engleskog izdanja, prevoditelji O. Kronja, V. Rapić, I. Bregovec, 1. hrvatsko izdanje, Školska knjiga 2017., L. G. Wade, ml., 2017.
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