00148 - Organic Chemistry (A-L)

Learning outcomes

Following the course, students will be able to understand the chemistry of the principal organic compounds and to apply the knowledges to bio-synthetic pathways. Moreover the student will be able to understand the reactivity of all organic compounds through the classification and behavior of functional group present in a complex organic molecules. The reactivity of functional group will be classified through simple rules and principles.

Course contents

1 . Orbitals. Electronic structures of atoms. Chemical bond. Ionic and covalent bond. Ibrids, polarity and electronegativity. Acids and bases. Nucleophiles and electrophiles. Arrows in organic chemistry.

2 . Functional groups. Descriptions. Atoms and connectivity. Principal functional groups. Alkanes, alkynes, alkenes, arenes, alcohols, phenols, alkylic halides, thiols, ketones, aldehdyes, amines, amides, acids, nitriles,

3 . Alkanes. Nomenclature. isomers. Structures. Alkanes and cycloalkanes. Strctural names. Conformational analysis of ethane, propane and butane. REaction of alkanes. Cyclohexane. STructure and conformations. Trans and cis isomers in cycloalkanes.

4 . Stereochemistry. Chirality and stereogenicity. Absolute configuation. Diastereoisomers and enantiomers. Compounds with two or more stereogenic centers. Number of stereoisomers. Projection.

5 . Alkenes . Mechanistic analysis in reactions. The interemdiates. Carbocations. Mayr's list. Electrophilic addition. Diene and carbocations. Stability. ati.

6. Alkynes. Nomenclature structure and acidity. REaction of acetylides. Anions and electrophilic addition.

7. Alkyl Halides. SN1 e SN2 reactions. Electrofugality scale.  Elimination reactions  E1 and E2.

8 . Arenes. Resoncance. Arene electrophilic substitutions.Idrocarburi aromatici. Risonanza. La sostituzione elettrofilica aromatica. Various reaction of benzene. A Friedel-Crafts addition. Different aromatic substitution. Substituents effect. Heteroaromatics. Hückel rules. Purine and pyrimidine. Nucleic acids. Porphyrins and corrines.

9 . Carbonyl compounds. Structure of the carbonyl. Reaction of nucleophiles to carbonyls. Acetals, hydride ions. Reactions with  NABH4 e LiAlH4. Metalloorganic compounds. Organolithium, zinc, magnesium, reagents. Grignard reagents. Keto;enolic tautomers. Enols and their reactivity. Ketones and aldehydes. Aldolic reactions. Reactions of aldol and enolates.

10. Alcohols, phenols, ethers. Nomenclature. Physic properties. Reduction and oxydation. REaction of epoxides. Thiols, aldehydes.

11. Carboxylic acids, and derivatives. Nomenclatures. Structure and acidity. Nucleophilic acylic substitution. Reaction of chloride. Malonic ester and acid. Alfa;beta unsaturated compounds.Claisen reactions.

12. Amine. Structure and reactivity. Reaction of amine. Alkaloyds.

13. Carbohydrates. Sugars emiacetals. Mutorotation. Conformation.  Conformation of monosacharides. Haworth projections. Glycosides and monosaccarides. Polysaccarides.

14. Aminoacides. Structures. Amminoacidi. Struttura. Nomi di tutti i 20 amminoacidi. Aminoacids basic and acids. Peptides. Structures. Analysis of peptides. Edman degradation. Synthesis of peptides. Enzymes. Proteins..

15. Lypides. Phospholipydes. Steroids. Biological membranes.

 

Readings/Bibliography

Organic Chemistry, J. McMurry

Teaching methods

Lessons and Power Points presentation available

Assessment methods

Written exam.
7 questions. 1 laboratory question.

Teaching tools

Course available:

 http://amscampus.cib.unibo.it/archive/00001782/

Office hours

See the website of Pier Giorgio Cozzi