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 structure and the action of organic compounds. As part of laboratory exercises, the synthesis of basic types of organic compounds is envisaged.
COURSE IMPLEMENTATION PROGRAM:
WEEK 1
Dienes, polyenes: resonance
WEEK 2
Aromatic compounds: properties and reactions, polycyclic aromatic compounds
WEEK 3
Reactions of aromatic compounds: basic mechanistic principle of electrophilic aromatic substitutions which include reactions of halogenation, nitration, sulfonation, alkylation and Friedel-Crafts acylations, understanding the influence of substituents on reactivity and directivity (regioselectivity) in the resulting products, heterocyclic compounds
WEEK 4
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).
WEEK 5
Partial exam I
WEEK 6
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.
WEEK 7
Aldehydes and ketones II: Aldol reactions: chemical reactivity of hydrogen atoms in the alpha 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.
WEEK 8, 9
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 interconversion of functional groups in acyl chloride and the mechanistic principle of nucleophilic elimination reaction on acyl group.
WEEK 10
Synthesis 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.
WEEK 11
Partial exam II
WEEK 12
Phenols and aryl halides: structure, acidity and nomenclature 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), application of phenol in Williams synthesis of ether, Kolbe synthesis of acetyl-salicylic acid (aspirin), Claisen rearrangement of allyl-phenyl ether, nucleophilic aromatic substitution addition elimination mechanism.
WEEK 13
Amines and related compounds with nitrogen: trigonal pyramidal structure of amines and structures of primary, secondary and tertiary amines, principles of amine synthesis, alkylation of ammonia, Gabriel synthesis, reductive amination of aldehydes or ketones, reduction of nitriles, oximes or amides, and Hoffman and Curtius rearrangement of amides, 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).
WEEK 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.
WEEK 15
Partial exam III
DEVELOPING 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
- rad u Praktikumu organske kemije: za izolaciju, pročišćavanje i identifikacije organskih produkata
STUDENT'S OBLIGATIONS:
It is obligatory to attend lectures and laboratory exercises in the Practicum of Organic Chemistry.
CONDITIONS FOR OBTAINING SIGNATURES:
Regular class attendance and completed laboratory exercises
TEACHING METHODS
Lectures and laboratory exercises
MANNER OF EXAMINATION OF KNOWLEDGE AND EXAMINATION
Continuous assessment of knowledge through colloquia, written and oral exam.
METHOD OF MONITORING THE QUALITY AND PERFORMANCE OF COURSES
Student survey
METHODOLOGICAL PREREQUISITIES
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
LEARNING OUTCOMES AT PROGRAM LEVEL
1. apply knowledge of chemistry, chemical technologies specifically related to modern applications, to biochemical systems
2. interpret biochemical cycles using the acquired knowledge of the overall metabolism strategy
3. assess the impact of structure and biological activity on various biomolecules
4. apply basic knowledge of applied chemistry in understanding the concept of the central dogma of molecular biology
TEACHING UNITS WITH ASSOCIATED LEARNING OUTCOMES AND EVALUATTION CRITERIA
Teaching unit
Aldehydes and ketones; nucleophilic additions to the carbonyl group
Learning outcomes
- use a dictionary of organic chemistry for carbonyl compounds, heterocycles, and nitrogen compounds
- draw correct spatial representations of organic molecules containing a carbonyl or amino group
Evaluation criteria
to judge the reaction path of the electrophilic addition of a given heterocyclic compound
Teaching unit
Carboxylic acids and derivatives; Amines and related compounds with nitrogen
Learning outcomes
- write acceptable transformations in nucleophilic addition reactions to the carbonyl group of aldehydes, ketones, carboxylic acids and derivatives
- compare the reactivity of amines depending on the structure
Evaluation criteria
- to conclude on the possibility of mutual translation of carboxylic acid derivatives into each other
- recommend preparing variously substituted aromatic compounds via diazonium salts from the corresponding amine
Teaching unit
Heterocyclic compounds, Biomolecules
Learning outcomes
propose the most probable reaction pathway in electrophilic addition reactions to various heterocyclic nuclei
Evaluation criteria
determine the basicity of individual heterocyclic nuclei depending on the heteroatom they possess
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