COURSE OBJECTIVES
To introduce the fundamental principles of modern organic chemistry and its applications in industry, and to provide students with an understanding of the relationship between the structure and activity of organic compounds. The laboratory component includes the synthesis of representative basic types of organic compounds.
COURSE CONTENT
Dienes and polyenes: resonance
Conjugated unsaturated systems: reactivity of compounds in terms of allylic substitution proceeding via the formation of an allylic radical intermediate, and explanation of its stability using molecular orbital theory and resonance theory; application of this reaction in allylic bromination; understanding the stability of conjugated 1,3-butadienes through electron delocalization (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).
Aromatic compounds: properties and reactions; polycyclic aromatic compounds.
Reactions of aromatic compounds: fundamental mechanistic principles of electrophilic aromatic substitution, including halogenation, nitration, sulfonation, alkylation, and Friedel?Crafts acylation; understanding the influence of substituents on reactivity and orientation (regioselectivity) of the resulting products.
Aldehydes and ketones I ? Nucleophilic addition to the carbonyl group: synthesis of aldehydes by reduction of the corresponding acid chlorides, esters, or nitriles; synthesis of ketones from alkynes, secondary alcohols, or nitriles; mechanism of acid-catalyzed addition of nucleophiles to the carbonyl group of aldehydes and ketones; mechanism of formation of hemiacetals and acetals; application of acetals as protecting groups in multistep syntheses; addition reactions of primary and secondary amines with aldehydes and ketones; mechanism of addition of hydrogen cyanide to the carbonyl group.
Aldehydes and ketones II ? Aldol reactions: chemical reactivity of hydrogen atoms in the ?-position relative to the carbonyl group and keto?enol tautomerism; reactions of enolate anions; mechanisms of acid- and base-catalyzed enolization; mechanisms of acid- and base-catalyzed halogenation of aldehydes and ketones; the aldol reaction and its synthetic applications.
Midterm Examination I
Carboxylic acids and their derivatives: structures and chemical reactivity of carboxylic acids and their derivatives, including acid chlorides, anhydrides, esters (lactones), amides (lactams), and nitriles; methods for the synthesis of carboxylic acids.
Synthesis of carboxylic acid derivatives: interconversion of functional groups in acid chlorides, anhydrides, and esters, and the mechanistic principles of nucleophilic acyl substitution reactions.
Synthesis and reactions of ?-dicarbonyl compounds. Enolate anion chemistry: synthesis of ?-keto esters by Claisen condensation and the mechanisms of nucleophilic addition and elimination reactions; synthesis of malonic acid derivatives by the Knoevenagel reaction and Michael addition, including the mechanisms of these reactions; the Mannich reaction and its mechanism.
Phenols and aryl halides: structure, acidity, and nomenclature of phenols; laboratory methods for the synthesis of phenols (e.g., hydrolysis of aryl diazonium salts); industrial synthesis of phenol by the base-catalyzed hydrolysis of chlorobenzene via nucleophilic aromatic substitution; application of phenols in the Williamson ether synthesis and the Kolbe synthesis of acetylsalicylic acid (aspirin); Claisen rearrangement of allyl phenyl ethers; nucleophilic aromatic substitution ? addition?elimination mechanism.
Amines and related nitrogen compounds: trigonal pyramidal structure of amines and structures of primary, secondary, and tertiary amines; arylamines; basic heterocyclic amines; biologically important amines; principles of amine synthesis by alkylation, the Gabriel synthesis, reductive amination of aldehydes or ketones, reduction of nitriles, oximes, or amides, and Hofmann and Curtius rearrangements of amides; Buchwald?Hartwig amination; reactions of amines.
Heterocyclic compounds
Flow organic synthesis
Computational chemistry ? basic principles
Midterm Examination II
DEVELOPMENT OF GENERAL AND SUBJECT-SPECIFIC STUDENT COMPETENCIES
Students who successfully complete this course will be able to:
recognize and use the terminology of organic chemistry;
draw correct structural representations of organic molecules;
write plausible transformations and reaction mechanisms for aromatic, carbonyl, and heterocyclic compounds;
apply knowledge of stereochemistry when analyzing mechanisms in organic chemistry;
work in the Organic Chemistry Laboratory for the isolation, purification, and identification of organic products.
STUDENT COURSE REQUIREMENTS AND METHODS OF COMPLETION
Attendance at lectures and completion of all laboratory exercises in the Organic Chemistry Laboratory are mandatory.
REQUIREMENTS FOR OBTAINING COURSE CREDIT
Regular attendance and completion of all laboratory exercises.
TEACHING METHODS
Lectures and laboratory exercises.
METHODS OF ASSESSMENT AND EXAMINATION
Continuous assessment through midterm examinations; a written and oral examination is required if the student does not achieve a passing result in the midterm examinations or wishes to improve the final grade.
COURSE QUALITY AND PERFORMANCE MONITORING
Student evaluation survey.
PREREQUISITES
Prerequisite for enrollment in the course: Completion of Organic Chemistry I lectures.
Prerequisite for taking the course examination: Successful completion of Organic Chemistry I.
COURSE LEARNING OUTCOMES
Upon successful completion of the course, students will be able to:
recognize and use the terminology of organic chemistry;
draw correct structural representations of organic molecules according to their functional groups;
apply knowledge of stereochemistry when analyzing mechanisms in organic chemistry;
write plausible transformations and reaction mechanisms for aromatic, carbonyl, and heterocyclic compounds;
compare the reactivities of different classes of organic compounds depending on their functional groups and reaction conditions;
propose the most likely reaction pathway for new molecules that have not been presented as examples in class;
perform standard preparative procedures used for the synthesis of simple organic compounds.
PROGRAMME-LEVEL LEARNING OUTCOMES
Upon successful completion of the programme, students will be able to:
solve qualitative and quantitative problems by applying appropriate chemical principles and theories;
present study-related materials orally and in writing to a professional audience;
apply standard laboratory procedures and instrumentation for preparative or analytical purposes in organic and inorganic systems;
interpret the results of laboratory observations and measurements, their significance, and their relationship to the corresponding theory;
assess the risks associated with the use of particular chemical substances or laboratory procedures.
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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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