LEARNING OUTCOMES

Understanding and reasoning are the basis for learning any scientific discipline. Mastering organic chemistry requires a deep understanding of some fundamental principles and the ability to use these principles to analyze, classify and make predictions. The program aims to help understand the relationships between structure and reactivity of the main functional groups, aromatic and heteroaromatic systems. The student will have to understand the fundamental principles of the chirality of organic compounds and the importance of this principle in biological systems, as well as in the synthesis of pharmacologically active chiral substances. The mechanistic study of reactions for the synthesis of model molecules will allow the student to reason and connect the reactivity of functional groups to the three-dimensional structures of the resulting compounds avoiding the student to memorize lists of reactions disconnected from each other. The student will have to develop skills in the design of a multistage synthesis using acquired synthetic strategies for solving problems. 

AIMS AND LEARNING OUTCOMES

Students will be directed to the study of organic chemistry to obtain a series of skills and abilities useful for completing scientific training that will enable them to be able to analyze, classify, explain and predict. Students will have to know the fundamental theories to solve organic chemistry problems with reasoning. They will have to be able to argue theories and master practical skills, complementary to each other, to obtain measurable results during the written and oral tests. The indicators for determining learning outcomes are:

1) Use of the periodic table for the construction of the electronic configuration of an atom;

2) Mastery in interpreting atomistic and molecular theories to understand the strength and nature of the chemical bond;

3) Use of molecular models for the determination of geometry and reactivity of molecules;

4) Master the fundamental concepts of stereochemistry;

5) Knowing how to visualize and orient the substituents in a molecule in space as well as being able to draw the interconversion of structural representations during a multistage reaction;

6) Classify the reactivity of organic compounds and functional groups within a molecule;

7) Recognize the acidic or basic nature and strength of a given compound by attributing the position of an acid-base balance;

8) Recognize the electrophilicity, nucleophilicity, and stability of a leaving group of a given atom or functional group;

9) Determine the relative stability of carbocations and radicals to understand the progress of a reaction for a specific mechanism;

10) Predict if a reaction occurs, or not, and by what mechanism;

11) Correctly draw curved arrows to represent the flow of electrons in an ionic reaction and radical processes;

12) Knowing how to represent the limit structures of resonance;

13) Use synthetic and retrosynthetic strategies for drug and molecule design;

14) Understanding the connections between the studied organic reactions and those occurring in nature and cell biology.

PREREQUISITES

Having passed the general and inorganic chemistry exam.

TEACHING METHODS

The course includes 3 weekly lectures of 2 hours each during which all the notions relating to the organic chemistry teaching program are transmitted to the students. Teaching materials to support the lessons (presentations, exercises and in-depth articles) are provided to students through the aulaweb platform. Fundamental texts are recommended for the study of theory and for carrying out the exercises. However, part of the lesson is carried out on the blackboard, using digital media and molecular models to educate the student in the two- and three-dimensional design of molecules and in the carrying out of chemical reactions with the relative mechanism. To face dynamic frontal lessons, the active participation of students is required in answering questions and carrying out exercises individually or in groups. Quizzes and exercises will be available on the aulaweb platform to keep the study updated, which allows a profitable accompaniment of the lessons throughout the teaching period of organic chemistry.

Tips on how to study: 1) keep the study of the weekly topics updated, never let them accumulate; 2) study the material in small teaching units and make sure you understand each new section before moving on to the next; 3) solve all the problems of the chapter; 4) write during the study in a theory and exercise notebook; 5) learn by teaching and explaining (study better in a group); 6) use molecular models during the study.

SYLLABUS/CONTENT

1. Elements of general chemistry: electronic structure and bond

Structure of the atom and distribution of electrons in the atom. Covalent bonds (polar and non-polar). Representations of the structure of a compound. Atomic and molecular orbitals. Valence bond theory, VSEPR model, and molecular orbital theory (TOM). Hybridization of carbon and formation of single, double, and triple bonds. Hybridization of other atoms (B, O, N) and related molecular geometries. The dipole moment of a bond and dipole moment of a molecule.

2. Acids and bases: fundamental concepts in organic chemistry

Organic acids and bases. Definition of Ka and pKa. Predict the location of an acid-base equilibrium via pKa. Factors affecting the strength of an acid and its pka. Acid-base theories of Arrhenius, Bronsted-Lowry, and Lewis. Use of curved arrows to represent the flow of electrons involved in an acid-base reaction.

3. Introduction to organic compounds: nomenclature, physical properties, and structure

Nomenclature of alkanes and cycloalkanes, alcohols and ethers, alkyl halides, and amines. Rotation around the single sigma bond (C-C). Conformational analysis of alkanes and their rotamers. Newman's projection of the conformational isomers of a linear alkane. Ring tension of cycloalkanes. Conformation analysis of cyclohexane. Conformers of cyclohexanes, mono-, di- and trisubstituted. Cis-trans isomerism of cycloalkanes. Cyclohexanes condensed in decalin and steroid hormones.

4. Isomers: the arrangement of atoms in space

Constitutional isomers and stereoisomers. Geometric isomerism (cis-trans and E / Z) in compounds with double bonds. Concept of chirality. Chiral molecules with asymmetrical center (stereogenic center). Representation of enantiomers and R, S descriptors for chiral carbons. Fischer projection. Origin of the optical activity of chiral compounds. Rotary optical power. Molecules with multiple chiral centers (diastereoisomers and meso compounds). Separation of enantiomers (racemic mixture).

5. Alkenes: structure, nomenclature, and introduction to reactivity

Reactivity of alkenes and use of curved arrows. Mechanism of a reaction between a nucleophile and an electrophile. Thermodynamics and kinetics of a reaction.

6. The reactions of alkenes

Addition of water and halogen acids to alkenes. Stability of carbocations. Transposition of carbocations. Regioselectivity of electrophilic addition (Markovnikov's rule) and radical addition (anti-Markovnikov) reactions. Hydroboration-oxidation of alkenes. Addition of halogens to alkenes. Addition of a peroxy acid to alkenes (epoxidation). Addition of ozone to alkenes (ozonolysis). Stereochemistry of addition reactions to alkenes: regioselective, stereoselective, or stereospecific reaction.

7. The reactions of alkynes

Nomenclature, structure, and reactivity of alkynes. Electrophilic additions to alkynes: introduction to keto-enol tautomerism. Catalytic hydrogenation of alkenes and its stereochemistry. The acidity of terminal alkynes. Use of acetylide ions in organic synthesis.

8. Electronic delocalization and its effect on stability, pKa, and products of a reaction

The bonds of benzene, resonance limit structures, and resonance hybrid. Predict the stability of resonance structures. Stability of dienes, allyl, and benzyl cations. Effect of electronic delocalization on pKa. Electron donation by resonance in a substituted benzene ring. Electronic attraction by resonance from the substituted benzene ring. Electrophilic addition 1,2 and 1,4 to conjugated dienes.Aromaticity criteria and Huckel's rule. Aromaticity according to the theory of molecular orbitals (Frost's rule). Aromatic heterocyclic compounds.

9. Reactions of substitution and elimination of alkyl halides

Mechanism of a bimolecular (SN2) and monomolecular (SN1) nucleophilic substitution reaction. Factors influencing SN2 and SN1 reactions. Elimination reactions of alkyl halides (E2 and E1). Stereochemistry and competitions between SN2, SN1, E2 and E1 reactions.

10. Reactions of alcohols, ethers, epoxides, and amines

Nucleophilic substitution reactions of alcohols. Elimination reaction (E1 and E2) of alcohols (dehydration). Stereochemistry of the dehydration reaction. Oxidation of alcohols. Nucleophilic substitution reactions of ethers and epoxides. Formation of cis and trans diols. Hofmann elimination reaction of a quaternary ammonium ion.

11. Organometallic compounds

Preparation of organolithium, organomagnesium, and organocuprates compounds. Palladium-catalyzed coupling reactions (Suzuki reaction).

12. Radicals

The relative stability of radicals. Radical halogenation of alkanes (chlorination and bromination). Radical addition of alkenes (anti-markonikov addition). Free radical reactions in biological systems and natural radical inhibitors.

13. Reactions of carboxylic acids and derivatives of carboxylic acids

Structure, physical properties and reactivity of carboxylic acid derivatives (acyl chloride, anhydride, ester, and amide).

14. Reactions of aldehydes and ketones

Reactivity of carbonyl compounds. Addition of strong and weak nucleophiles to the carbonyl carbon. Formation of imines and enamines. Formation of acetals and hemiacetals as protecting groups of the carbonyl group. Wittig reaction. Nucleophilic addition to a,b-unsaturated aldehydes and ketones in the presence of weak (conjugated-1,4 addition) and strong (direct 1,2-addition) nucleophiles.

15. Reactions to  a carbon

The acidity of hydrogen to carbonyl derivatives. Keto-enol tautomerism. Halogenation of carbon a of aldehydes and ketones. Formation of the kinetic and thermodynamic enolate ion. Carbon alkylation with catalyzed base. Stork reaction. Aldol addition for the formation of a b b-hydroxy aldehyde or a b-hydroxy ketone. Cross aldol addition. Claisen condensation. Malonic synthesis and acetoacetic synthesis. Aldol condensation and Claisen condensation in biological systems.

16. Reactions of benzene and substituted benzenes

Nomenclature of monosubstituted benzenes. Aromatic electrophilic substitution reactions (SEAr): halogenation, nitration, sulfonation, acylation and Friedel-Crafts alkylation). Chemical transformations of substituents on the benzene ring. Effect of substituents on the reactivity of a benzene ring. Effect of substituents on the orientation of a SEAr.

17. Pentatomic and hexatomic aromatic heterocyclic compounds.

Aromaticity of pyrrole, furan, thiophene and pyridine. Heterocyclic amines of biological importance: histidine, histamine, porphyrin, purines and pyrimidines. Paal-Knorr synthesis of pyrrole, furan and thiophene. Hantzsch synthesis of pyridine. Aromatic electrophilic substitutions on pyrrole, thiophene, furan and pyridine. Vilsmeier reaction. Pyridine N-oxide. Chichibabin reaction.

18. The organic chemistry of carbohydrates

Classification of carbohydrates: aldoses and ketosis. Annotation D and L to describe the configurations of carbohydrates. Pyranose sugars (six-term cycles) and furanose sugars (5-term cycles). Anomeric carbon of glucose and the hemiacetal structures of a-D-glucose and b-D-glucose. Chair conformation of D-glucose.

19. Amino acids

Configuration of amino acids. Methods of synthesis of amino acids: Hell-Volhard-Zelinshi reaction and Strecker synthesis

RECOMMENDED READING/BIBLIOGRAPHY

Paula Yurkains Bruice, CHIMICA ORGANICA, Ed. EdiSES  

Brown, CHIMICA ORGANICA, Ed. EdiSES  

John McMurry, CHIMICA ORGANICA, Ed. Piccin  

Peter Vollahardt, Chimica Organica, Ed. Zanichelli 

Solomons Fryhle, CHIMICA ORGANICA, Ed. Zanichelli 

Botta et all, CHIMICA ORGANICA, Ed. Edi-Ermes