Università degli Studi di Urbino Carlo Bo / Portale Web di Ateneo


ORGANIC CHEMISTRY I
CHIMICA ORGANICA I

A.Y. Credits
2021/2022 10
Lecturer Email Office hours for students
Fabio Mantellini from Monday to Friday by telephone contact (0722 303445; 0722 303446).
Teaching in foreign languages
Course with optional materials in a foreign language English
This course is entirely taught in Italian. Study materials can be provided in the foreign language and the final exam can be taken in the foreign language.

Assigned to the Degree Course

Pharmaceutical Chemistry and Technology (LM-13)
Curriculum: PERCORSO COMUNE
Date Time Classroom / Location
Date Time Classroom / Location

Learning Objectives

The educational objective of the course is the students' understanding of the structural characteristics, of the nomenclature, of the chemical-physical properties and of the reactivity of the main classes of organic compounds through the study of the main reaction mechanisms.The course setting follows the classical criterion of the systematic description of the various functional groups, in both structural and reactionary terms. Some general topics such as the kinetic and thermodynamic aspects, acidity and basicity, stereochemistry, the relationships between structure and physical properties, will be treated separately. Other ones such as resonance, equilibria, electronic and steric factors, etc. are inserted into the discussion of functional groups in order to stimulate understanding and memorization by analyzing concrete examples.

Program

COVALENT BOND AND MOLECULAR GEOMETRY

Electronic structure of atoms. Model of binding of Lewis. Functional groups. Bond angles and molecular geometry. Polar and non-polar molecules. Covalent bond: molecular orbital theory and valence bond. Resonance. Molecular orbitals delocalized systems. Length and strength of the bonds in alkanes, alkenes and alkynes.

ALKANES AND CYCLOALKANES

Structure of alkanes. Constitutional isomerism in alkanes. IUPAC nomenclature of alkanes.  Cycloalkanes. Conformation of alkanes and cycloalkanes. Isomers cis, trans in cycloalkanes. Physical properties of alkanes and cycloalkanes. Reactions of alkanes. Sources and importance of alkanes.

STEREOCHEMISTRY AND CHIRALITY

Stereoisomery, chirality of molecules. Nomenclature of chiral centers. Not cyclic molecules with two or more chiral centers. Cyclic molecules with two or more chiral centers. Properties of the stereoisomers. Optical activity: chirality as is revealed in the laboratory. Meaning of chirality in the biological world. Examples of chiral drugs. Amino acids. Separation of enantiomers: resolution.

ACIDS AND BASES

Acids and bases: Arrhenius, Brønsted-Lowry and Lewis theories. Acid dissociation constants, pKa and strength of acids and bases. Equilibrium position in the acid-base reactions. How to calculate the equilibrium constant in acid-base reactions. Thermochemical and mechanisms of acid-base reaction. Molecular structure and acidity.

ALKENES

Structure of alkenes. Physical properties of alkenes. Alkenes of natural origin: terpenes. Electrophilic additions: hydrohalic acids, water, bromine and chlorine, formation of halohydrins. Regioselectivity in the reactions of electrophilic addition. Oxymercuration / reduction of alkenes. Hydroboration / oxidation. Reduction. Reactants or products containing chiral centers

ALKYNE

Structure and nomenclature of alkynes. Physical properties of alkynes. Acidity of 1-alkyne. Preparation of alkynes. Electrophilic additions to alkynes. Hydration of alkynes to give aldehydes and ketones. Reduction of alkynes. Organic synthesis involving alkynes.

ALKYL HALIDES

Structure, nomenclature and physical properties of alkyl halides. Preparation of alkyl halides by halogenation of alkanes and by the addition of hydrogen halides to alkenes.

Allylic halogenation. Nucleophilic substitution in alkyl halides. Mechanisms of aliphatic nucleophilic substitution. Experimental evidence and the mechanisms for SN1 and SN2; comparison of nucleophilic substitution reactions. beta-elimination: mechanisms and experimental evidence. Competition between substitution and elimination.

.ALCOHOLS

Structure, nomenclature and physical properties of alcohols. Acidity of alcohols. Reactions of alcohols with active metals. Conversion of alcohols into alkyl halides and sulfonates. Dehydration of alcohols catalyzed by acid. Pinacol rearrangement. Oxidation of alcohols. Thiols.

ETHERS, EPOXIDES AND SULPHIDES

Structure, nomenclature and physical properties of ethers. Preparation of ethers. Reactions of ethers. Silyl ethers as protecting groups. Epoxides: structure and nomenclature. Synthesis of epoxides. Reactions of epoxides. Ethylene oxide and epichlorohydrin: buiding block in organic synthesis. Crown ethers. Sulphides.

ORGANOMETALLIC COMPOUNDS

Magnesium and lithium organometallic compounds of. Reactive lithium dialchilcuprati (Gilman reagents). Carbenes.

ALDEHYDES AND KETONES

Structure, nomenclature and physical properties of aldehydes and ketones. Nucleophilic additions to the carbonyl of carbon, oxygen, sulfur and nitrogen nucleophiles. Wittig reaction. Keto-enol tautomerism. Oxidation, reduction. Reactions to the alpha carbon. Cannizzaro's reaction.

CARBOXYLIC ACIDS

Structure, nomenclature and physical properties of carboxylic acids. Acidity. Preparation of carboxylic acids. Reduction. Esterification. Conversion to acid chlorides. Decarboxylation.

ESTERS, AMIDES, ACYL ANHYDRIDES, ACYL CHLORIDES

Structure, nomenclature and physical properties of esters, amides, acyl anhydrides, and acid chlorides. Nucleophilic  acyl substitution. Reactions with water: hydrolysis. Reactions with alcohols. Reactions with ammonia and amines. Reactions of acid chlorides with the salts of carboxylic acids. Interconversion of carboxylic acid derivatives. Reactions with organometallic compounds.

ANIONS ENOLATE AND ENAMINES

Formation and reaction of enolate anions. Aldol condensation. Claisen and Dieckmann condensations. The aldol and Claisen condensations in the biological world. Enamines. Acetoacetic synthesis. Malonic ester synthesis. Addition conjugated to alpha, beta-unsaturated-carbonyl compounds. Cross reactions of enolates using LDA. Knoevenagel condensation.

SYSTEMS CONJUGATED

Stability of the conjugated diene. Electrophilic additions to conjugated dienes. Diels Alder reaction.

AROMATIC COMPOUNDS

Structure, nomenclature and physical properties of aromatic compounds. Phenols. Reactions in benzyl position. Electrophilic aromatic substitution. Poly-substitution reactions. Nucleophilic aromatic substitution. Heterocycles.

AMINES

Structure, nomenclature and physical properties of amines. Chiral amine and quaternary ammonium ions. Basicity of the amines. Reactions with acids. Preparation of amines. Reactions with nitrous acid. Hofmann elimination. Cope elimination.

NITROGEN ORGANIC COMPOUNDS

Imines, Mannich reaction, isocyanates, nitriles, amides, oximes, azo compounds, diazoalkanes, azides.

Bridging Courses

General and Inorganic Chemistry and Physical Chemistry.

Learning Achievements (Dublin Descriptors)

D1- KNOWLEDGE AND UNDERSTANDING The student must demonstrate the knowledge of the organic reactions associated with the main functional groups that distinguish the organic substances. Moreover he will have to demonstrate to be able to design synthetic sequences that involve more reactions that allow to elaborate processes of formation of complex molecules. These skills will be assessed through the resolution of a multi-step synthesis.

D2-APPLYING KNOWLEDGE AND UNDERSTANDING The student will have to show to apply his / her own knowledge, comprehension skills and ability to solve problems related to the behavior of organic substances inserted in a general context. These skills will be verified both  through specific oral applications.

D3-AUTONOMY OF JUDGMENT The student must have acquired knowledge such as to allow him to recognize and predict the behavior of complex molecules according to the reaction conditions to which they are subjected.

D4-COMMUNICATION The student must demonstrate that he / she is able to clearly communicate his / her conclusions, as well as the underlying knowledge and rationale, with an adequate chemical language, to specialist and non-specialist interlocutors. These skills will be verified through an oral test.

D5-LIFELONG LEARNING SKILLS The student must develop the ability to drive his path of scientific growth in a critical and autonomous way, being able to correctly use the study material provided by the teacher and the in-depth material that he himself can obtain. These abilities, as far as possible, will be stimulated by the teacher proposing in-depth studies and providing exercises to be solved at home during the course, which will then be explained and discussed during the lessons or hours of support activities.

Teaching Material

The teaching material prepared by the lecturer in addition to recommended textbooks (such as for instance slides, lecture notes, exercises, bibliography) and communications from the lecturer specific to the course can be found inside the Moodle platform › blended.uniurb.it

Supporting Activities

Different types of exercises and exam texts are available on the Blended portal.


Didactics, Attendance, Course Books and Assessment

Didactics

Frontal lessons and exercises 

Attendance

Constant attendance at lessons is strongly recommended.

Course books

W. H. Brown, C. S. Foote, B. L. Iverson, E. V. Anslyn, Organic Chemistry
 

Assessment

The assessment of the student's preparation takes place through a written test containing five organic synthesis exercises with several steps to which is added an exercise aimed at determining the absolute configuration of three stereocenters. The duration of the test is three hours.

Admission to the oral exam is subject to passing the written exam with a grade equal to or greater than 18/30.

The oral exam will test the knowledge of the reaction mechanisms and the ability to interconnect the topics covered during the course. The oral exam has an average duration of 30 minutes. The final grade in the exam is the arithmetic average between the grade obtained in the written and oral tests.

In case of limitations due to the pandemic, the exam is only oral. In this case, the verification of the student's preparation takes place through the preliminary resolution of organic synthesis with several steps followed by a discussion to verify the knowledge of the reaction mechanisms and the ability to interconnect the topics covered during the course. The average duration of the test is one hour.

Additional Information for Non-Attending Students

Didactics

All the teaching material is available on the Blended platform for students who decide not to attend the course

Attendance

Constant attendance at lessons is strongly recommended.

Course books

W. H. Brown, C. S. Foote, B. L. Iverson, E. V. Anslyn, Organic Chemistry

Assessment

The assessment of the student's preparation takes place through a written test containing five organic synthesis exercises with several steps to which is added an exercise aimed at determining the absolute configuration of three stereocenters. The duration of the test is three hours.

Admission to the oral exam is subject to passing the written exam with a grade equal to or greater than 18/30.

The oral exam will test the knowledge of the reaction mechanisms and the ability to interconnect the topics covered during the course. The oral exam has an average duration of 30 minutes. The final grade in the exam is the arithmetic average between the grade obtained in the written and oral tests.

In case of limitations due to the pandemic, the exam is only oral. In this case, the verification of the student's preparation takes place through the preliminary resolution of organic synthesis with several steps followed by a discussion to verify the knowledge of the reaction mechanisms and the ability to interconnect the topics covered during the course. The average duration of the test is one hour.

« back Last update: 08/09/2021

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