Applied Pharmaceutical Sciences

FINAL PART (3 CFU) Carboxylic acids and the acidity of the O-H bond. Structure and nomenclature. Preparation. Acidity. Inductive effects in aliphatic and aromatic acids. Substituted benzoic acids. Sulfonic acids. Carboxylic acids and their derivatives – Nucleophilic acyl substitution. Structure and bonding. Nomenclature. Nucleophilic acyl substitution: reaction of acid chlorides, of anhydrides, of carboxylic acids, of esters, of amides. Substitution reactions of carbonyl compound in enols and enolates. Direct enolate alkylation. Malonic ester synthesis. Acetoacetic ester synthesis. Carbonyl condensation reactions. The aldol reaction. The Claisen reaction. The Michael reaction. Secondary Metabolism: Introduction and classification of main pathways. note: time spent for each issue is indicated in the Italian version.

For an easy approach to the course, it is advisable to have acquired the knowledge of general chemistry.

1- Gorzynski Smith J.: Fondamenti di Chimica Organica, McGrow-Hill, 2009. ISBN 978 88 386 6488-5. 2- Botta B., a cura di: Chimica Organica Essenziale, Edi-Ermes, 2012. ISBN 978-88-08-7051-354-7. 3- Paul M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali (II ed. Italiana), Piccin. ISBN: 978-88-299-2234-5

Blendeed lessons using Prodigit system

Attendance at course is not mandatory, however it is highly encouraged the frequency of lessons for a better understanding of the topics. For an easy understanding of the topics covered in the course it is recommended to have passed the General and Inorganic Chemistry exam.

The exam consists of a written test (lasting one hour) that serves for admission to the oral exam, followed by the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade. The written test consists in 12-15 exercises, which may also contain practical or theoretical questions on the whole program. The student will attend the oral exam if he reaches the status of “ammesso”. To access the written exam, students must register on the E-learning platform. The written test lasts only one session namely January/February, June/July, September, and November. The oral exam consists of 3 questions on the whole program (average exam duration: 30 minutes). To achieve a score of 30/30 cum laude, the student must demonstrate that he has acquired excellent knowledge of all the topics covered during the course, showing a natural ability to link between them quickly. To access the oral exam, students must register on INFOSTUD.

Blendeed lessons using Prodigit system

Structure and chemical bonds The chemical bond. Electronegativity and polarity of the bond. Polarity of molecules. Carbon hybridization: ethane, ethylene, acetylene. Bond length and bond strength. Representation of organic structures. Lewis structures. The shape of the molecules. Resonance [2 hours]. Acids and bases Acids and bases by Brønsted-Lowry. Reactions of acids and bases by Brønsted-Lowry. Acid strength and pKa. Prediction of equilibrium. Factors that affect acidity. Acids and bases by Lewis. Functional groups. Intermolecular forces. Physical properties. Functional groups and reactivity [2 hours]. Alkanes and cycloalkanes Introduction. IUPAC nomenclature for alkanes and cycloalkanes. Common names. Physical properties. Conformation of acyclic alkanes (ethane, butane). Cycloalkanes. Cyclohexane (chair conformation, ring inversion). Cyclohexanes substituted (mono- and di-substituted) [2 x 2 hours]. Alkenes IUPAC nomenclature (use of cis/trans and E/Z convention). Physical properties. Preparation of alkenes. Electrophilic addition reactions: hydrohalogenation (Markovnikov’s rule, stereochemistry); hydration; halogenation (stereochemistry) [3 x 2 ore]. Alkynes IUPAC nomenclature. Physical properties. Preparation. Reactivity: acidity of terminal alkynes; hydrohalogenation; halogenation; hydration. Reactions of the acetylide anions [2 hours]. Conjugation, resonance and dienes Conjugation. Resonance and allylic carbocations. The resonance hybrid. Delocalization of electrons, hybridization and geometry. Conjugated dienes: 1,3-butadiene [2 hours]. Stereochemistry The two main classes of isomers. Chiral and achiral molecules. Stereogenic centers. Absolute R/S configuration. Diastereoisomers. Compounds with two or more stereogenic centers. Mesoforms and racemic mixtures. Physical properties of enantiomers (optical activity, specific rotation, enantiomeric excess) and diastereoisomers. Chemical properties of enantiomers [2 x 2 hours]. Organic reactions Equations of organic reactions. Type of organic reactions (substitution, elimination, addition). Cleavage and formation of bonds (radicals, carbocations, carbanions). Bond dissociation energy. Thermodynamics (equilibrium constant and free energy changes) [concepts given during the different lessons]. Alkyl halides and substitution reactions Introduction. IUPAC nomenclature. Physical properties. Polarity of the carbon-halogen bond. Nucleophilic substitution (halide, leaving group, nucleophile, solvent effect). SN2 and SN1 mechanism (kinetics, stereochemistry, nature of the halide, solvent effect). Stability of carbocations. Factors determining the SN2 or SN1 mechanism [2 x 2 hours]. Alkyl halides and elimination reactions General features of elimination. Alkenes (C=C double bond, cis/trans isomers, stability). E2 and E1 elimination mechanism (kinetics, nature of halide). Zaitsev’s rule (regioselective and stereoselective reactions). Factors determining the E2 or E1 mechanism [2 x 2 hours]. Alcohols, ethers and epoxides Structure, IUPAC nomenclature, physical properties. Preparations. Reactivity of alcohols: dehydration, reaction with halogenidric acids. Reactivity of ethers with strong acids. Reaction of epoxides with nucleophiles and with acids [2 x 2 hours]. Benzene and aromatic compounds The structure of benzene. Nomenclature. Stability of benzene. Hückel's rule. Polycyclic aromatic hydrocarbons. Aromatic heterocycles (pyridine, pyrrole) [2 hours]. Electrophilic aromatic substitution (SEAr) reaction General mechanism. Benzene halogenations (mechanism), nitration and sulphonation. Friedel-Crafts alkylation and acylation. Aromatic electrophilic substitution on substituted benzenes (effect of substituents on reactivity and orientation) [2 hours]. Amines Structure, IUPAC nomenclature, physical properties. Preparation by direct nucleophilic substitution and by reduction of functional groups containing nitrogen; reductive amination [2 hours]. Introduction to the carbonyl chemistry. General reactivity of the carbonyl group: the nucleophilic addition reaction [2 hours]. Definition and IUPAC nomenclature. Carbon nucleophiles: addition of cyanidric acid and Grignard reagents. Oxygen nucleophiles: addition of water and alcohols. Hemiacetals and acetals formation [2 hours]. Nitrogen nucleophiles: addition of ammonia and primary and secondary amines. Imines and enamines. Reduction of aldehydes and ketones [2 x 2 hours].

For an easy understanding of the topics covered in the course it is recommended to have acquired the basics of general and inorganic chemistry.

One of the following books: 1) Autori Vari, Chimica Organica Essenziale, Edi-Ermes, Milano, 2018, 2° edizione (a cura di Bruno Botta). 2) John McMurry, Fondamenti di Chimica Organica, Zanichelli, Bologna, 2005. 3) William H. Brown, Thomas Poon, Introduzione alla Chimica Organica, EdiSES S.r.l., Napoli, III Ed. For the chemistry of natural products: Paul M. Dewick, Chimica, Biosintesi e Bioattività delle Sostanze Naturali, Piccin-Nuova Libraria, 2012.

The course consists of frontal lectures and numerical exercises on the blackboard that are intended to prepare students for the written test. During the lessons, the teacher stimulates the students with questions related to what it has just been presented, with the aim of making them participate and stimulate the study at home, lesson by lesson. Students are invited to read the various textbooks recommended at the beginning of the course and to find, on them, the discussion of the various topics proposed in class.

Attendance to the course is not mandatory, but strongly recommended.

The exam consists of a written test (lasting 1 hour) that serves for the admission to the oral exam, followed by the oral test. The written test is not given a grade, but only an admission decision (ADMITTED/NOT ADMITTED) to the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade. The written test is structured in 12 open-ended exercises and may also contain a theoretical question on a reaction mechanism proposed in class. To access the written exam, students must register on the E-learning platform. The validity of the test is limited to one session only, namely January/February, June/July, September, November). The oral exam consists of 3 questions on the whole program (average exam duration: 30 minutes). To achieve a score of 30/30 cum laude, the student must demonstrate that he has acquired excellent knowledge of all the topics covered during the course, showing a natural ability to quickly link between them. To access the oral exam, students must register on INFOSTUD.

The course consists of frontal classes and numerical exercises on the blackboard that are intended to prepare students for the written test. During the lessons, the teacher stimulates the students with questions related to what it has just been presented, with the aim of making them participate and stimulate the study at home, lesson by lesson. Students are invited to read the various textbooks recommended at the beginning of the course and to find, on them, the discussion of the various topics proposed in class.

FINAL PART (3 CFU) Carboxylic acids and the acidity of the O-H bond. Structure and nomenclature. Preparation. Acidity. Inductive effects in aliphatic and aromatic acids. Substituted benzoic acids. Sulfonic acids. Carboxylic acids and their derivatives – Nucleophilic acyl substitution. Structure and bonding. Nomenclature. Nucleophilic acyl substitution: reaction of acid chlorides, of anhydrides, of carboxylic acids, of esters, of amides. Substitution reactions of carbonyl compound in enols and enolates. Direct enolate alkylation. Malonic ester synthesis. Acetoacetic ester synthesis. Carbonyl condensation reactions. The aldol reaction. The Claisen reaction. The Michael reaction. Secondary Metabolism: Introduction and classification of main pathways. note: time spent for each issue is indicated in the Italian version.

For an easy approach to the course, it is advisable to have acquired the knowledge of general chemistry.

1- Gorzynski Smith J.: Fondamenti di Chimica Organica, McGrow-Hill, 2009. ISBN 978 88 386 6488-5. 2- Botta B., a cura di: Chimica Organica Essenziale, Edi-Ermes, 2012. ISBN 978-88-08-7051-354-7. 3- Paul M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali (II ed. Italiana), Piccin. ISBN: 978-88-299-2234-5

Blendeed lessons using Prodigit system

Attendance at course is not mandatory, however it is highly encouraged the frequency of lessons for a better understanding of the topics. For an easy understanding of the topics covered in the course it is recommended to have passed the General and Inorganic Chemistry exam.

The exam consists of a written test (lasting one hour) that serves for admission to the oral exam, followed by the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade. The written test consists in 12-15 exercises, which may also contain practical or theoretical questions on the whole program. The student will attend the oral exam if he reaches the status of “ammesso”. To access the written exam, students must register on the E-learning platform. The written test lasts only one session namely January/February, June/July, September, and November. The oral exam consists of 3 questions on the whole program (average exam duration: 30 minutes). To achieve a score of 30/30 cum laude, the student must demonstrate that he has acquired excellent knowledge of all the topics covered during the course, showing a natural ability to link between them quickly. To access the oral exam, students must register on INFOSTUD.

Blendeed lessons using Prodigit system

FINAL PART (3 CFU) Carboxylic acids and the acidity of the O-H bond. Structure and nomenclature. Preparation. Acidity. Inductive effects in aliphatic and aromatic acids. Substituted benzoic acids. Sulfonic acids. Carboxylic acids and their derivatives – Nucleophilic acyl substitution. Structure and bonding. Nomenclature. Nucleophilic acyl substitution: reaction of acid chlorides, of anhydrides, of carboxylic acids, of esters, of amides. Substitution reactions of carbonyl compound in enols and enolates. Direct enolate alkylation. Malonic ester synthesis. Acetoacetic ester synthesis. Carbonyl condensation reactions. The aldol reaction. The Claisen reaction. The Michael reaction. Secondary Metabolism: Introduction and classification of main pathways. note: time spent for each issue is indicated in the Italian version.

For an easy approach to the course, it is advisable to have acquired the knowledge of general chemistry.

1- Gorzynski Smith J.: Fondamenti di Chimica Organica, McGrow-Hill, 2009. ISBN 978 88 386 6488-5. 2- Botta B., a cura di: Chimica Organica Essenziale, Edi-Ermes, 2012. ISBN 978-88-08-7051-354-7. 3- Paul M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali (II ed. Italiana), Piccin. ISBN: 978-88-299-2234-5

Blendeed lessons using Prodigit system

Attendance at course is not mandatory, however it is highly encouraged the frequency of lessons for a better understanding of the topics. For an easy understanding of the topics covered in the course it is recommended to have passed the General and Inorganic Chemistry exam.

The exam consists of a written test (lasting one hour) that serves for admission to the oral exam, followed by the oral test. Once the oral exam is also held, the student acquires the 9 total credits of the teaching (CFU), with a final grade. The written test consists in 12-15 exercises, which may also contain practical or theoretical questions on the whole program. The student will attend the oral exam if he reaches the status of “ammesso”. To access the written exam, students must register on the E-learning platform. The written test lasts only one session namely January/February, June/July, September, and November. The oral exam consists of 3 questions on the whole program (average exam duration: 30 minutes). To achieve a score of 30/30 cum laude, the student must demonstrate that he has acquired excellent knowledge of all the topics covered during the course, showing a natural ability to link between them quickly. To access the oral exam, students must register on INFOSTUD.

Blendeed lessons using Prodigit system