CHIMICA ORGANICA

The aims of this course is to transmit to the student a good and solid grounding in the basic principles of organic chemistry through study of the structure-function relationships of organic compounds, the chemistry of functional groups, and reactions of organic compounds, which are required for the successful completion of other courses of general background, such as pharmaceutical chemistry, pharmacology and biochemistry

Upon successful completion of this course, students will be able to know the structure and nomenclature of the principal functional groups of organic compounds, their chemistry and reactivity.

At the end of the course the students will:

1. Know and recall the fundamental principles of organic chemistry that include chemical bonding, nomenclature, structural isomerism, stereochemistry, chemical reactions and mechanism.
2. Name the functional groups and different class of organic compounds.
3. Recognize the basic practical skills for the synthesis and analysis of organic compounds.
4. Predict the reactivity of an organic compound from its structure.
5. Develop basic skills for the multi-step synthesis of organic compounds.
6. Justify a reasonable mechanism for a chemical reaction.

The teaching is given as lectures and exercises

Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes, in line with the planned programme.

For a better learning of the course contents, it is recommended an active participation of the students towards the topics covered during lectures and classroom exercises.

 

In case of students with disabilities and/or SLD, in accordance with the Italian Law (170/2010), it is possible to adapt assessment and study methods, without modifying learning objectives; this support includes dispensatory measures and compensatory tools. To request the service, the student must inform professor at the beginning of the course or at least 30 days before the exam.

Furthermore, it is possible to contact Prof. Teresa Musumenci, CInAP (Centro per l’Integrazione Attiva e Partecipata - Servizi per le Disabilità e/o DSA) referent teacher of our Department.

The students must know the fundamental of General and Inorganic Chemistry and in particular:

Periodic table – Atomic structure and electronic configuration – Ionic and covalent bonds – Atomic and molecular orbitals – Valence bond theory – Structural formulas – Hybrid carbon, oxygen and nitrogen orbitals – Acids and bases, definitions of pKa and pH and equilibrium – Acidity and basicity according to Brønsted-Lowry and Lewis – Thermodynamics and kinetics – Values of ΔH - Catalysis.

The aforementioned topics can be found in the first chapters of any Organic Chemistry textbook.

Mandatory (Degree Course regulations)

PART 1: An Introduction to the Study of Organic Chemistry

1. Remembering General Chemistry: Electronic Structure and Bonding

2. Acids and Bases: Central to Understanding Organic Chemistry

3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure

 

PART 2: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization

4. Isomers: The Arrangement of Atoms in Space

5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity

6. The Reactions of Alkenes – The Stereochemistry of Addition Reactions

7. The Reactions of Alkynes – An Introduction to Multistep Synthesis

8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction –• Aromaticity and Electronic Effects: An Introduction the Reactions of Benzene

 

PART 3: Substitution and Elimination Reactions

9. Substitution and Elimination Reactions of Alkyl Halides

10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

11. Organometallic Compounds

12. Radicals

 

PART 4: Carbonyl Compounds

15. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

16. Reactions of Aldehydes and Ketones – More Reactions of Carboxylic Acid Derivatives

17. Reactions at the α-Carbon

 

PART 5: Aromatic Compounds

18. Reactions of Benzene And Substituted Benzenes

19. Reactions of Amines

19/1. The chemistry of Heteroaromatic Compounds

 

PART 6: Bioorganic Compounds

20. The Organic Chemistry of Carbohydrates

21. The Organic Chemistry of Amino Acids, Peptides, and Proteins

25. The Organic Chemistry of Lipids

26. The Organic Chemistry of Nucleic Acids

1. Chimica Organica – P. Y. Bruice – 3^a Ed. 2017 – EdiSES, ISBN 9788879599351 (with a molecular model kit).
2. Chimica Organica – AA. VV. a cura di B. Botta, – 2ª Ed. 2016 – Edi-Ermes, ISBN 9788870514780
3. Chimica Organica – P. C. Vollhardt, N. E. Schore, – 4ª Ed. 2016 – Zanichelli, ISBN 9788808721235
4. Esercizi risolti di Chimica Organica – N. E. Schore e K. P. C. Vollhardt – 4^a Ed. 2016 – Zanichelli, ISBN 9788808436900

The level of acquisition of the educational objectives will be verified through a final exam consisting of a written test followed by an oral interview. Passing the written test with 18/30 is an essential condition for accessing the oral interview.

Booking for the exam is mandatory; it is active up to four days before the date reported in the exam calendar.

The written test (90 minutes) consists of 30 multiple choice questions (5 answers, only one exact – 1 pt. for correct, -0.25 for wrong and 0 for not given answer). It is to be held without the help of notes or book and includes the entire program.

The written test will be passed with a minimum of 18/30.

The oral exam consists of a discussion (about 30 minutes), aimed at ascertaining the level of knowledge and understanding reached by the student regarding the theoretical and methodological contents indicated in the program; it will take place at least two days after the written test and the date will be communicated on the Department website, "news" section.

The final evaluation will be established on the basis of the scores achieved in both tests. The oral exam is not aimed at raising the grade obtained in the written test but, with a negative result, it may result in rejection and the written test must be repeated.

As a result of special conditions, the verification of learning can also be carried out remotely.

For logistical reasons, the number of questions and the time required for their execution can be modified.

Assign the IUPAC name including stereochemistry to the following compound and indicate the number of possible stereoisomers.

Sort the following compounds in order of increasing acidity.

Indicate among the following species the strongest nucleophile in a polar protic solvent.

Propose a mechanism for the following transformation.

Write the product and mechanism of the following reaction.

Complete the following reactions.

Describe the elongation of the chain of a monosaccharide.