Our course catalogue for the accademic year 2022/2023 is currently being updated

Objectives

1.a. General expected learning outcomes
Organic chemistry is a chemistry discipline involving the scientific study of the structure, reactivity, properties and applications of compounds which are formed mainly by carbon atoms, forming covalent bonds, both from natural and artificial sources The general objective, is to provide students with the knowledge and competences necessary to understand the structure, reactivity and synthetic methods of different functional groups, and the mechanisms of organic reactions. For a CTF student, this learning is essential, because most drugs are organic compounds, and their biological activity depends on their interaction with biological targets, which are also organic compounds. This knowledge will allow the student to be able to understand the fundamental synthetic methodology for the construction of biologically active compounds. Furthermore, stereochemical expertise will be essential for improving the understanding of the drug-receptor interactions, a crucial topic in different next courses.

1.b. Specific expected learning outcomes
1. Knowledge and understanding
The specific objectives consist in acquiring the following knowledge and expertise:
1) to understand the importance of stereochemistry on the reactivity of organic compounds;
2) to understand the relationship between structure and reactivity for the different functional groups;
3) to acquire the basic knowledge of organic chemistry in order to understand the basic mechanism of organic reactions.
4) to acquire the basic knowledge of the organic synthesis
5) to apply the main concepts of stereochemistry to the reactivity of organic compounds.
6) to predict the reactivity and the physical properties of organic compounds.
7) to speculate about mechanistic aspect of the organic reactions.
8) to design the synthesis of organic molecules through their retrosynthetic analysis.

2. Applying knowledge and understanding
At the end of the course the student will be able to apply the acquired knowledge appropriately by adopting the terminology and the chemical symbology of the subject; furthermore the student will be able how to apply the knowledge learned to the design of the synthesis of simple organic molecules.

3. Making judgements
The Organic Chemistry 1 course is devoted to provide students with the adequate knowledge to be independent in solving the examination problems or exercises.
This ability will be acquired by the means of frontal lesson and guided exercitations that will be organized in ascending order of the difficulties they pose.

4. Communication skills
In order to improve the exposure ability, students will be constantly encouraged to communicate their ideas to both specialists and non specialists audiences. The Erasmus programme will enable students to improve their communications skills, by exchanging informations, problems and solutions.

5. Learning skills
Teaching materials, available on line will support students during the lessons even thought studying the recommended text book is essential to acquire the skills and the competence that are necessary to perform the final exam.

Channels

A - L

GIANCARLO FABRIZI GIANCARLO FABRIZI   Teacher profile

Programme

Section 1. Acids and bases (5 hours)
Arrhenius, Lowry-Brönsted e, and Lewis acids and bases. Factors influencing the strength of Lowry-Brönsted acids and bases: hybridization, polarizability, electronegativity, inductive effect, field effect, resonance, hydrogen bond, solvent.
Section 2. Hydrocarbons and 1,3-Dienes (18 hours)
Alkanes and cycloalkanes
Nomenclature, hybridization, structure, structural isomers, conformation (torsional strain, angle strain), hybridization and bond angle (cyclopropane). Newman projections. Haworth projections.Reactivity: radical halogenation [mechanism, selectivity (transition state and Hammond’s postulate)]. Radicals: structure, stability (hyperconjugation, resonance). Bicycles: nomenclature.
Alkenes
Nomenclature, hybridization, structure, stability, geometric isomerism, E-Z rules. Reactivity: addition of HX (X = halogens) [ionic (carbocations: structure, stability, carbocation rearrangement) and radical (HBr) mechanism], water (specific acid catalysis), halogens, synthesis of halohydrins, hydroboration-oxidation (regio- e stereochemistry), epoxidation (reaction with peracids), palladium-catalyzed hydrogenation and hydrogenation heats, Heck reaction, oxidation with OsO4 (oxidation numbers), addition of carbenes (carbenes from chloroform), Simmon-Smith reaction. Allylic halogenation: influence of the concentration of Br2 and temperature on the addition to double bond/allylic bromination ratio. Reaction with N-bromosuccinimide. Stability of the allylic radical. Regioselectivity
1,3-Dienes
Structure. Stability. Reactions: 1,2 and 1,4 additions (kinetic and themodynamic control).
Alkynes
Nomenclature, hybridization, structure. Reactivity: palladium-catalyzed addition of hydrogen, addition of HX (X = halogen) (vinylic cations: hybridization, stability), addition of halogens, addition of water (catalyzed by sulfuric acid and Hg(II) salts), hydroboration-oxidation with internal and terminal (disiamylborane) alkynes, acidity of terminal alkynes (addition and nucleohilic substitution reactions of acetylides).
Section 3. Stereochemistry (4 hours)
Fundamentals of stereochemistry
Stereoisomers. Chirality. Chiral and stereogenic center. Enantiomers and diastereoisomers. Symmetry elements: center, axis, plane. Enantiomers: nomenclature (Cahn, Ingold, and Prelog priority rules). Optical rotation. Racemates. Specific rotation. Enantiomeric excess. Compounds containing more than one chiral center (diastereoisomers and meso isomers). Fischer projections. Resolution of racemates. Stereoselectivity and stereospecificity.
Section 4. Alkyl halides, alcohols, ethers and epoxides (14 hours)
Alkyl halides
Structure and IUPAC nomenclature. Nucleophilic substitution (SN), nucleophilicity and basicity. SN1: mechanism, stereochemistry, ion pairs, factors influencing the SN1 reaction (alkyl halide, leaving group, nucleophile, solvent (protic solvents, polar aprotic solvents, apolar aprotic solvents). SN2: mechanism, stereochemistry, factors influencing the SN2 reaction (alkyl halide, leaving group, nucleophile, solvent). SN1 vs SN2 (influence of the alkyl group, solvent, and nucleophile). beta-Elimination (E). E1: mechanism, regiochemistry (Saitseff’s rule). E2: mechanism, regiochemistry, stereochemistry. E2 in cyclic systems. E1 vs E2: influence of the alkyl halide, solvent, and base. SN1 vs E1 and SN2 vs E2. alfa-Elimination: formation of carbenes. Formation of organometallic compounds: alkyllithium compounds, alkylmagnesium compounds.
Alcohols
Nomenclature. Reactivity: acidity in the gas phase and in solution, synthesis of ethers (Williamson and acid-catalyzed dehydration), esters, and tosylates, addition to C-C double bonds (tetrahydropyranyl protecting group), oxidation (mechanism with chromic acid and pyridinium chlorochromate), reaction with PBr3, with SOCl2 in the absence (SNi) and in the presence of tertiary amines or pyridine, dehydration of alcohols and tosylates. Pinacol rearrangement.
Ethers
Nomenclature. Reactivity: reaction with con HX (X = halogens). Epoxides: nomenclature, ring opening (acid-catalyzed, with nucleophiles), reaction with Grignard reagents (synthesis of Grignard reagents and their reaction with water and carbon dioxide).
Section 5. Aldehydes and ketones, carboxylic acids and their derivatives (12 hours)
Aldehydes and ketones
Nomenclature. Addition reactions: specific acid-catalyzed addition, reaction with boron and aluminum hydrides (reactivity of alkoxy derivatives of boron and aluminum hydrides), with terminal alkynes, Grignard reagents, HCN, water, alcohols (acetals as protecting groups). Addition-elimination reactions: Wittig reaction, reaction with primary and secondary amines. Bayer-Villiger reaction. Reduction to hydrocarbons: Clemmensen and Wolff-Kishner reactions.
Carboxylic acids
Nomenclature. Reactivity: acid-base reactions, reactions with LiAlH4, with alcohols, with SOCl2, with PBr3.
Carboxylic acid derivatives
Acyl halides, anhydrides, esters, lactones, amides, lactames, imides, nitriles - Nomenclature. Reactivity: reaction with water [acyl chlorides, anhydrides, esters, (esters from 1°, 2°, and 3° alcohols), amides, nitriles], with alcohols (acyl chlorides, anhydrides, esters), with carboxylic acid salts (acyl chlorides), with ammonia and amines [acyl chlorides, anhydrides, esters, with Grignard reagents (esters), with LiAlH4 (esters, amides, nitriles), Hoffmann’s degradation, Reformatsky’s reaction.
Section 6. Enols, enolates and α,β-Unsaturated aldehydes and ketones (7 hours)

Enols and enolates
Keto-enol tautomerism (acid- and base-catalyzed), factors influencing the keto-enol equilibrium (hydrogen bond, resonance), thermodinamic and kinetic control in the formation of enolate anions in the presence of LDA. a-Bromination of ketones (under acid and basic conditions), Hell-Vohlard-Zelinski reaction. Aldol condensation, Aldol condensation-dehydration (under acid and basic conditions) intramolecular aldol condensation, crossed aldol condensation, Claisen and Dieckmann condensations, acetoacetic and malonic syntheses.
α,β-Unsaturated aldehydes and ketones
1,4- and 1,2-Addition (reversible and irreversible). Reaction with Grignard reagents and anions from 1,3-dicarbonyl compounds. Robinson annulation.
Section 7. Aromatic compounds, phenols and amines
Aromatic compounds
Aromaticity. Huckel rule. Aromatic, antiaromatic and non aromatic compounds. Aromatic ions. Heteroaromatics. Nomenclature. Electrophilic aromatic substitution: mechanism, substituent effects, halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation. Nucleophilic aromatic substitution: addition-elimination, elimination-addition (evidences in favor of benzyne), via phenyl cation.
Phenols
Nomenclature. Reactivity: acidity, synthesis of esters and ethers, electrophilic aromatic substitution, Reimer-Tiemann reaction, synthesis of azo compounds.
Amines
Nomenclature. Chirality: tertiary amines and carbanions. Pyramidal inversion. Chirality of armonium salts. Eliminations of armonium salts (Hofmann rule, variable transition state and steric strain). Reactivity: basicity (in gas phase and in solution), reaction with alkyl halides, with carbonyl compounds, reactions of aromatic amines with HNO2 (arenediazonium salts, coupling with anilines and phenols). Enamines - Alkylation, acylation, and conjugate addition.
Section 8. Summary and exercises (8 hours)

Adopted texts

B. Botta. Chimica Organica II edizione. Edi-Ermes
For exercises session:
1) S. Cacchi, F. Nicotra “ESERCIZI DI CHIMICA ORGANICA ” Casa Ed. Ambrosiana, 1999
2) N. E. Schore, K. P. Vollhartdt “ESERCIZI RISOLTI DI CHIMICA ORGANICA ” Zanichelli

Prerequisites

Students are expected to know the following fundamentals of chemistry: hybridization, resonance, aromaticity, fundamentals of thermodinamics (entalpy, Gibbs energy, entropy), chemical equilibria, fundamentals of chemical kinetics, reaction rate, transition state.

Study modes

The course (9 CFU) is provided through traditional lessons integrated with exercises. The lessons are held in classrooms where there are devices suitable for projecting the slides of the course, available to CTF students on the Sapienza E-learning platform. The exercises, provided throughout the course, cover all the topics covered during the theoretical lessons and prepare students for the written test. There are several summarizing sessions in which different quiz that are representative of those given to the exam, are shown. Students have at their disposal self-assessment tests related to all the chapters dealt with during the theoretical course.

Exam modes

In order to acquire the CFU of the course, by the end of the class students have to pass the final exam that is planned every month ( other than in August). Midterm exam are not provided.
In order to facilitate the student in their study planning, the date of the exam may be designated during the whole session. The final exam consists in a written examination (essay test) and in an oral examination; its purpose is to certify the acquired knowledge about organic chemistry.
In order to be eligible for the oral examination students must pass the written examination. This latter has the duration of 20 minutes and consist in three random-selected exercises which are prepared by the examination board. Each student will have his own test. In order to get a positive results, students must correctly solve at least two of the three proposed exercise. The examination board reserves the right to consider eligible for the oral examination those students whose written test is considered adequate even if not completely responding to the previous request.
The oral examination result is expressed in thirtieths and depends on:
1) evaluation of written exam;
2) evaluation of general and specific knowledge about all the subject of the class;
3) clarity in exposure ;
4) ability to create links between the studied topics.
Minumum to pass examination is (18/30) .Students exhibiting a detailed knowledge will pass with first-class honours( 30/30 cum laude).
The exam may be performed in every programmed session.

Exam reservation date start Exam reservation date end Exam date
21/11/2019 07/01/2020 13/01/2020
21/11/2019 03/02/2020 10/02/2020
01/01/2020 13/04/2020 20/04/2020
01/01/2020 01/06/2020 08/06/2020
01/01/2020 29/06/2020 06/07/2020
01/01/2020 01/09/2020 07/09/2020
01/01/2020 02/11/2020 09/11/2020
01/01/2020 06/01/2021 11/01/2021
16/11/2020 17/01/2021 18/01/2021

M - Z

ANTONELLA GOGGIAMANI ANTONELLA GOGGIAMANI   Teacher profile

Programme

Section 1. Acids and bases (5 hours)
Arrhenius, Lowry-Brönsted e, and Lewis acids and bases. Factors influencing the strength of Lowry-Brönsted acids and bases: hybridization, polarizability, electronegativity, inductive effect, field effect, resonance, hydrogen bond, solvent.
Section 2. Hydrocarbons and 1,3-Dienes (18 hours)
Alkanes and cycloalkanes
Nomenclature, hybridization, structure, structural isomers, conformation (torsional strain, angle strain), hybridization and bond angle (cyclopropane). Newman projections. Haworth projections.Reactivity: radical halogenation [mechanism, selectivity (transition state and Hammond’s postulate)]. Radicals: structure, stability (hyperconjugation, resonance). Bicycles: nomenclature.
Alkenes
Nomenclature, hybridization, structure, stability, geometric isomerism, E-Z rules. Reactivity: addition of HX (X = halogens) [ionic (carbocations: structure, stability, carbocation rearrangement) and radical (HBr) mechanism], water (specific acid catalysis), halogens, synthesis of halohydrins, hydroboration-oxidation (regio- e stereochemistry), epoxidation (reaction with peracids), palladium-catalyzed hydrogenation and hydrogenation heats, Heck reaction, oxidation with OsO4 (oxidation numbers), addition of carbenes (carbenes from chloroform), Simmon-Smith reaction. Allylic halogenation: influence of the concentration of Br2 and temperature on the addition to double bond/allylic bromination ratio. Reaction with N-bromosuccinimide. Stability of the allylic radical. Regioselectivity
1,3-Dienes
Structure. Stability. Reactions: 1,2 and 1,4 additions (kinetic and themodynamic control).
Alkynes
Nomenclature, hybridization, structure. Reactivity: palladium-catalyzed addition of hydrogen, addition of HX (X = halogen) (vinylic cations: hybridization, stability), addition of halogens, addition of water (catalyzed by sulfuric acid and Hg(II) salts), hydroboration-oxidation with internal and terminal (disiamylborane) alkynes, acidity of terminal alkynes (addition and nucleohilic substitution reactions of acetylides).
Section 3. Stereochemistry (4 hours)
Fundamentals of stereochemistry
Stereoisomers. Chirality. Chiral and stereogenic center. Enantiomers and diastereoisomers. Symmetry elements: center, axis, plane. Enantiomers: nomenclature (Cahn, Ingold, and Prelog priority rules). Optical rotation. Racemates. Specific rotation. Enantiomeric excess. Compounds containing more than one chiral center (diastereoisomers and meso isomers). Fischer projections. Resolution of racemates. Stereoselectivity and stereospecificity.
Section 4. Alkyl halides, alcohols, ethers and epoxides (14 hours)
Alkyl halides
Structure and IUPAC nomenclature. Nucleophilic substitution (SN), nucleophilicity and basicity. SN1: mechanism, stereochemistry, ion pairs, factors influencing the SN1 reaction (alkyl halide, leaving group, nucleophile, solvent (protic solvents, polar aprotic solvents, apolar aprotic solvents). SN2: mechanism, stereochemistry, factors influencing the SN2 reaction (alkyl halide, leaving group, nucleophile, solvent). SN1 vs SN2 (influence of the alkyl group, solvent, and nucleophile). beta-Elimination (E). E1: mechanism, regiochemistry (Saitseff’s rule). E2: mechanism, regiochemistry, stereochemistry. E2 in cyclic systems. E1 vs E2: influence of the alkyl halide, solvent, and base. SN1 vs E1 and SN2 vs E2. alfa-Elimination: formation of carbenes. Formation of organometallic compounds: alkyllithium compounds, alkylmagnesium compounds.
Alcohols
Nomenclature. Reactivity: acidity in the gas phase and in solution, synthesis of ethers (Williamson and acid-catalyzed dehydration), esters, and tosylates, addition to C-C double bonds (tetrahydropyranyl protecting group), oxidation (mechanism with chromic acid and pyridinium chlorochromate), reaction with PBr3, with SOCl2 in the absence (SNi) and in the presence of tertiary amines or pyridine, dehydration of alcohols and tosylates. Pinacol rearrangement.
Ethers
Nomenclature. Reactivity: reaction with con HX (X = halogens). Epoxides: nomenclature, ring opening (acid-catalyzed, with nucleophiles), reaction with Grignard reagents (synthesis of Grignard reagents and their reaction with water and carbon dioxide).
Section 5. Aldehydes and ketones, carboxylic acids and their derivatives (12 hours)
Aldehydes and ketones
Nomenclature. Addition reactions: specific acid-catalyzed addition, reaction with boron and aluminum hydrides (reactivity of alkoxy derivatives of boron and aluminum hydrides), with terminal alkynes, Grignard reagents, HCN, water, alcohols (acetals as protecting groups). Addition-elimination reactions: Wittig reaction, reaction with primary and secondary amines. Bayer-Villiger reaction. Reduction to hydrocarbons: Clemmensen and Wolff-Kishner reactions.
Carboxylic acids
Nomenclature. Reactivity: acid-base reactions, reactions with LiAlH4, with alcohols, with SOCl2, with PBr3.
Carboxylic acid derivatives
Acyl halides, anhydrides, esters, lactones, amides, lactames, imides, nitriles - Nomenclature. Reactivity: reaction with water [acyl chlorides, anhydrides, esters, (esters from 1°, 2°, and 3° alcohols), amides, nitriles], with alcohols (acyl chlorides, anhydrides, esters), with carboxylic acid salts (acyl chlorides), with ammonia and amines [acyl chlorides, anhydrides, esters, with Grignard reagents (esters), with LiAlH4 (esters, amides, nitriles), Hoffmann’s degradation, Reformatsky’s reaction.
Section 6. Enols, enolates and α,β-Unsaturated aldehydes and ketones (7 hours)

Enols and enolates
Keto-enol tautomerism (acid- and base-catalyzed), factors influencing the keto-enol equilibrium (hydrogen bond, resonance), thermodinamic and kinetic control in the formation of enolate anions in the presence of LDA. a-Bromination of ketones (under acid and basic conditions), Hell-Vohlard-Zelinski reaction. Aldol condensation, Aldol condensation-dehydration (under acid and basic conditions) intramolecular aldol condensation, crossed aldol condensation, Claisen and Dieckmann condensations, acetoacetic and malonic syntheses.
α,β-Unsaturated aldehydes and ketones
1,4- and 1,2-Addition (reversible and irreversible). Reaction with Grignard reagents and anions from 1,3-dicarbonyl compounds. Robinson annulation.
Section 7. Aromatic compounds, phenols and amines
Aromatic compounds
Aromaticity. Huckel rule. Aromatic, antiaromatic and non aromatic compounds. Aromatic ions. Heteroaromatics. Nomenclature. Electrophilic aromatic substitution: mechanism, substituent effects, halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation. Nucleophilic aromatic substitution: addition-elimination, elimination-addition (evidences in favor of benzyne), via phenyl cation.
Phenols
Nomenclature. Reactivity: acidity, synthesis of esters and ethers, electrophilic aromatic substitution, Reimer-Tiemann reaction, synthesis of azo compounds.
Amines
Nomenclature. Chirality: tertiary amines and carbanions. Pyramidal inversion. Chirality of armonium salts. Eliminations of armonium salts (Hofmann rule, variable transition state and steric strain). Reactivity: basicity (in gas phase and in solution), reaction with alkyl halides, with carbonyl compounds, reactions of aromatic amines with HNO2 (arenediazonium salts, coupling with anilines and phenols). Enamines - Alkylation, acylation, and conjugate addition.
Section 8. Summary and exercises (8 hours)

Adopted texts

B. Botta. Chimica Organica II edizione. Edi-Ermes
Exercises books
1) S. Cacchi, F. Nicotra “ESERCIZI DI CHIMICA ORGANICA ” Casa Ed. Ambrosiana, 1999
2) N. E. Schore, K. P. Vollhartdt “ESERCIZI RISOLTI DI CHIMICA ORGANICA ” Zanichelli, 2016

Prerequisites

Students are expected to know the following fundamentals of chemistry: hybridization, resonance, aromaticity, fundamentals of thermodinamics (entalpy, Gibbs energy, entropy), chemical equilibria, fundamentals of chemical kinetics, reaction rate, transition state.

Study modes

The course (9 CFU) is provided through traditional lessons integrated with exercises. The lessons are held in classrooms where there are devices suitable for projecting the slides of the course, available to CTF students on the Sapienza E-learning platform. The exercises, provided throughout the course, cover all the topics covered during the theoretical lessons and prepare students for the written test. There are several summarizing sessions in which different quiz that are representative of those given to the exam, are shown. Students have at their disposal self-assessment tests related to all the chapters dealt with during the theoretical course. Attendance to lectures and exercises, although very useful for achieving the course's educational objectives, is not mandatory.

Exam modes

In order to acquire the CFU of the course, by the end of the class students have to pass the final exam that is planned every month ( other than in August). Midterm exam are not provided.
In order to facilitate the student in their study planning, the date of the exam may be designated during the whole session. The final exam consists in a written examination (essay test) and in an oral examination; its purpose is to certify the acquired knowledge about organic chemistry.
In order to be eligible for the oral examination students must pass the written examination. This latter has the duration of 20 minutes and consist in three random-selected exercises which are prepared by the examination board. Each student will have his own test. In order to get a positive results, students must correctly solve at least two of the three proposed exercise. The examination board reserves the right to consider eligible for the oral examination those students whose written test is considered adequate even if not completely responding to the previous request.
The oral examination result is expressed in thirtieths and depends on:
1) evaluation of written exam;
2) evaluation of general and specific knowledge about all the subject of the class;
3) clarity in exposure ;
4) ability to create links between the studied topics.
Minumum to pass examination is (18/30) .Students exhibiting a detailed knowledge will pass with first-class honours( 30/30 cum laude).
The exam may be performed in every programmed session.

Exam reservation date start Exam reservation date end Exam date
21/11/2019 06/01/2020 13/01/2020
21/11/2019 03/02/2020 10/02/2020
01/01/2020 13/04/2020 20/04/2020
01/01/2020 02/06/2020 08/06/2020
01/01/2020 29/06/2020 06/07/2020
01/01/2020 01/09/2020 07/09/2020
01/01/2020 02/11/2020 09/11/2020
01/01/2020 06/01/2021 18/01/2021
Course sheet
  • Academic year: 2019/2020
  • Curriculum: Curriculum unico
  • Year: Second year
  • Semester: First semester
  • SSD: CHIM/06
  • CFU: 9
Activities
  • Attività formative di base
  • Ambito disciplinare: Discipline Chimiche
  • Exercise (Hours): 12
  • Lecture (Hours): 64
  • CFU: 9.00
  • SSD: CHIM/06