COURSE OBJECTIVE:
Present the basic principles of modern organic chemistry and its application in industry.
COURSE IMPLEMENTATION PROGRAM:
WEEK 1
Carbon compounds and chemical bonds, classes of compounds, types of reactions in organic chemistry.
WEEK 2
Alkanes and cycloalkanes; Conformational and geometric isomerism.
Laboratory - entrance colloquium for introductory exercises (recrystallization, distillation, thin layer chromatography, qualitative elemental analysis of unknown sample).
1. Task - solved problems related to the teaching units processed in the first 2 weeks via e-learning.
WEEK 3
Alkenes, dienes, polyenes, alkynes: properties, synthesis, addition reactions.
Laboratory - Recrystallization of substances from water and determination of melting point. Processing the results of laboratory exercises and making written reports.
2. Task - solved problems related to the teaching unit covered in the 3rd week via e-learning.
WEEK 4
Stereochemistry: optical isomerism, constitutional isomers and stereoisomers, enantiomers and chiral molecules, (R) - (S) system, diastereomers.
Laboratory - Recrystallization of substances from ethanol and determination of melting point. Processing the results of laboratory exercises and making written reports.
3. Task - solved problems related to the teaching unit processed in the 4th week via e-learning.
WEEK 5
1. Written partial test.
WEEK 6
Aromatic compounds: properties and reactions, polycyclic aromatic compounds.
Laboratory - Determination of unknown substance by thin layer chromatography. Processing the results of laboratory exercises and making written reports.
WEEK 7
Alkyl halides - ionic reactions: nucleophilic substitution (SN1 and SN2) and elimination reactions (E2 and E1), stereochemistry of reactions.
Laboratory - Qualitative elemental analysis of an unknown sample. Processing the results of laboratory exercises and making written reports.
4. Task - solved problems related to the teaching units processed in the 6th and 7th week via e-learning.
WEEK 8
Alcohols, phenols, aryl halides, ethers, thiols, properties and reactions.
Laboratory - entrance colloquium for preparative exercises (Reactions of nucleophilic substitution of SN2 and SN1: synthesis and isolation of compounds).
WEEK 9
Aldehydes and ketones: nucleophilic additions to the carbonyl group.
Laboratory - Nucleophilic substitution reaction of SN1: synthesis and isolation of tert-butyl chloride. Processing the results of laboratory exercises and making written reports.
5. Task - solved problems related to the teaching units processed in the 8th and 9th week via e-learning.
WEEK 10
2. Written partial exam.
WEEK 11
Carboxylic acids and derivatives.
Laboratory - Esterification reaction: synthesis and isolation of ethyl acetate. Processing the results of laboratory exercises and making written reports.
WEEK 12
Amines and related compounds with nitrogen. Heterocyclic compounds.
Laboratory - Cannizzaro reaction: synthesis and isolation of benzyl alcohol and benzoic acid. Processing the results of laboratory exercises and making written reports.
6. Task - solved problems related to the teaching units processed in the 11th and 12th week via e-learning.
WEEK 13
Synthetic polymers. Carbohydrates and lipids. Amino acids and proteins, biochemical processes.
Laboratory - Diazotization and copulation: synthesis and isolation of beta-naphtholorange. Processing the results of laboratory exercises and making written reports.
WEEK 14
Determination of the structure of organic compounds by spectroscopic methods.
Laboratory - final colloquium.
WEEK 15
3. Written partial test.
DEVELOPMENT OF GENERAL AND SPECIFIC COMPETENCIES OF STUDENTS:
General competencies:
Applying the basic principles of modern organic chemistry and literature or our own experimental data in solving of chemical-engineering problems.
Special competencies:
Applying basic synthesis reactions and reactions involving alkanes, alkenes, alkynes, alcohols, aromatic compounds, carbonyl compounds, carboxylic acids and their derivatives and using the instrumentation used for preparative purposes.
Recognition and using of basic organic chemistry vocabulary. Drawing the correct structures of organic molecules. Writing acceptable transformations and mechanisms for alkanes, alkenes, alkynes, alkyl halides, alcohols, aromatic, carbonyl and heterocyclic compounds.
Using knowledge of 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:
Students are required to attend lectures.
Students are required to do all the lab exercises.
Students are required to submit assignments via e-learning.
Students are required to access partial exams and colloquia (related to laboratory exercises).
CONDITIONS FOR OBTAINING A SIGNATURE:
70% attendance at lectures.
Completed laboratory exercises, prepared and submitted papers, passed the final colloquium in laboratory exercises.
Dedicated assignments through e-learning.
TEACHING METHODS:
Lectures (ex cathedra).
Lecture through e-learning.
Laboratory exercises (practical work in groups under the supervision of an assistant).
Consultations by arrangement with students.
METHOD OF EXAMINATION OF KNOWLEDGE AND EXAMINATION:
Entrance colloquia fom laboratory exercises.
Final colloquium fom laboratory exercises.
3 Compulsory written partial exams during the semester (60% of points on each of the tests bring exemption from the written exam).
Written exam (requires 55% points to pass).
Oral exam.
METHOD OF MONITORING THE QUALITY AND PERFORMANCE OF COURSES:
Student survey.
METHODOLOGICAL PREREQUISITES:
Passed exam in General and Inorganic Chemistry.
COURSE LEARNING OUTCOMES:
1. To analyze and draw correctly the structure of carbon compounds, binding in organic molecules and the structure of molecules in space.
2. To use knowledge of stereochemistry when analyzing mechanisms in organic chemistry.
3. To define and identify the basic types of organic reactions and explain the basic reaction mechanisms with the recognition of reactive intermediates of reactions.
4. To identify functional groups in molecules and define classes of compounds and apply IUPAC rules for naming organic compounds.
5. To carry out standard preparative procedures used to obtain simple organic compounds.
6. To propose and devise the most probable reaction pathway for new molecules not given as examples in class.
LEARNING OUTCOMES AT PROGRAM LEVEL:
1. describe the phenomena in the field of chemical engineering using vocabulary and apparatus of the fundamental sciences - mathematics, physics and chemistry
2. define chemical engineering problems, which includes their analysis and formulation in order to solve them using fundamental principles
3. solve real chemical engineering problems by scientific approach
4. interpret results of independently planned experiments, with guidance of a senior chemical engineer
5. apply principles of professional and ethical responsibility
6. demonstrate capability of learning on their own and recognizing the need for lifelong learning
TEACHING UNITS WITH ASSOCIATED LEARNING OUTCOMES AND EVALUATION CRITERIA:
Teaching unit
1. Carbon compounds and chemical bonds, classes of compounds, division of reactions in organic chemistry. Alkanes and cycloalkanes. Conformational and geometric isomerism. Alkenes, dienes, polyenes, alkynes: addition reactions.
Learning outcomes:
- To identify classes of compounds, chemical bonds and hybridizations
- To draw correct structural representations of alkanes and cycloalkanes, alkenes, dienes, polyenes, alkynes
- To use knowledge of conformational and geometric isomerism to define the stereochemistry of molecules
- To write acceptable reaction mechanisms for alkanes, alkenes, alkynes
- To propose the most stable conformers of alkanes by Newman projections
- To compare the stability of differently substituted cyclohexane rings
Evaluation criteria:
- to know how to classify given compounds according to groups of organic compounds
- be able to determine the most stable conformations of alkanes and cycloalkanes
- to apply knowledge of the stability of carbocations in addition reactions to the double bond of alkenes and dienes
2. Stereochemistry: optical isomerism, constitutional isomers and stereoisomers, enantiomers and chiral molecules, (R) / (S) system, diastereomers. Aromatic compounds. Alkyl halides. Alcohols, phenols, aryl halides, ethers, thiols.
Learning outcomes:
- to use the (R) / (S) system to determine the absolute configuration of the achiral carbon
- to draw correctly enantiomeric representations of asymmetric organic molecules
- to use a knowledge of stereochemistry to distinguish different types of stereoisomers
- to write an acceptable mechanisms of electrophilic aromatic substitution reactions
- to compare the reactivities of alkyl halides in nucleophilic substitution reactions and in elimination reactions
- to discuss the difference in reactivity of alcohol, phenol and related compounds
Evaluation criteria:
-to apply the rules of determining the absolute configuration to new examples of compounds with an achiral carbon atom
- for a given monosubstituted aromatic compound determine in which direction the entry of the second substituent is directed depending on the nature of the bound group
- to determine the direction of reactions and the mechanism of a given alkyl halide depending on the structure of the substrate and the strength of the nucleophile
3. Aldehydes and ketones; nucleophilic additions to the carbonyl group. Carboxylic acids and derivatives. Amines and related compounds with nitrogen. Heterocyclic compounds.
Learning outcomes:
- to use the dictionary of organic chemistry for carbonyl compounds, heterocycles and nitrogen compounds
-to draw correct spatial representations of organic molecules containing a carbonyl or amino group
- to write acceptable transformations in nucleophilic addition reactions to the carbonyl group of aldehydes, ketones, carboxylic acids and derivatives
- to compare the reactivity of amines depending on the structure
- to propose the most probable reaction pathway in electrophilic addition reactions to various heterocyclic nuclei
Evaluation criteria:
- to judge the reaction path of electrophilic addition of a given heterocyclic compound
- to conclude on the possibility of mutual translation of carboxylic acid derivatives into each other
-to recommend the preparation of variously substituted aromatic compounds via diazonium salts a from the corresponding amine
- to determine the basicity of individual heterocyclic nuclei depending on the heteroatom they possess
4. Synthetic polymers. Amino acids, proteins and nucleic acids. Carbohydrates. Determination of the structure of organic compounds by spectroscopic methods.
Learning outcomes:
- to use knowledge of the types of polymerization on specific examples of obtaining synthetic polymers
- to know the basic structural features of essential amino acids, proteins and nucleic acids
- to recognize the structure of the most important carbohydrates
- to get acquainted and discuss the most important methods for determining the structure of organic compounds
- to compare the most important methods for determining the structure of organic compounds
Evaluation criteria:
- on the basis of the acquired knowledge, to propose the ways of modifying the structure of the synthetic polymer in order to improve the properties
- to apply and connect knowledge about the structure of essential amino acids with the structure of protein
- to be familiar with the structure of nucleic acids
- to be familiar with the structure of basic and most important carbohydrates
- to conclude and compare the application of individual methods for determining the structure of organic compounds
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J. McMurry, "Osnove organske kemije", Zrinski d.d. Čakovec, 2016.
H. Hart, L. E. Craine, D. J. Hart, Ch. M. Hadad, "Organic Chemistry-a short course", Twelfth Edition, Houghton Mifflin Company, Boston, USA, 2007.,
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Organska kemija, 7. izdanje (englesko), 1. izdanje (hrvatsko), prijevod: O. Kronja, V. Rapić, I. Bregovec, S. H. Pine, "Organska kemija" (prijevod I. Bregovec, V. Rapić), Školska knjiga, Zagreb, 1994.;
V. Rapić, "Nomenklatura organskih spojeva", Školska knjiga, III izmijenjeno i nadopunjeno izdanje, Zagreb, 2004., L. Wade ml., Školska knjiga;, 2017.
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