ORGANIC CHEMISTRY 1

Degree course: 
Corso di First cycle degree in Chemical Sciences and Technologies
Academic year when starting the degree: 
2013/2014
Year: 
1
Academic year in which the course will be held: 
2013/2014
Course type: 
Basic compulsory subjects
Credits: 
9
Period: 
Second semester
Standard lectures hours: 
72
Detail of lecture’s hours: 
Lesson (72 hours)
Requirements: 

Prerequisites: Students are required to be familiar with the principles of general chemistry and in particular Valence Bond theory, chemical equilibrium, Broensted-Lowry and Lewis acidity and basicity.

Assessment: 
Voto Finale

Teaching objectives and expected learning outcomes:

The students at their first year of course in Chemistry and Industrial Chemistry, are expected to acquire the basic knowledge of Organic Chemistry including the following topics: * Basic principles of nomenclature to assign the correct name to organic compounds according to the IUPAC (International Union of Pure and Applied Chemistry) rules; * Mechanisms of organic reactions; * Functional groups and reactivity and interconversion. At the end of the course the students will be able to: * Identify simple synthetic pathways for the construction of simple organic molecules; * Draw organic reaction mechanisms applied to specific substrates * Name organic molecules and describe their reactivity using the appropriate terminology.

Course program:

Reminds of the atomic theory, atomic orbitals, hybridation, nionic and covalent bonds, molecular orbitals. Electonegativity and bond polarization. Non bonding interaction,. Inductive effects and resonance stabilization. Acids and Bases in Organic Chemistry. Main functional groups, nomenclature and reactivity Nucleophiles and electrophiles. Carbocations and their transpositions. Carbanions and radicals. Biasics of Organic Stereochemistry (molecular symmetry, chirality, stereocenters, absolute and relative configuration descriptors). Alkanes and cycloalkanes: nomenclature and structure. Conformational stereoisomerism of cyclic and open chains. Alkenes and polyalkenes: geometric stereoisomerism; electrophilic addition to alkenes and stereochemistry of addition reactions (regioselectivity, stereospecifity and stereoselectivity), addition of strong acids, alogens, hydroboartions, oxymercuriation, oxidation. Reactivity of conjugated dienes: 1,4-addition, Diles-Alder reaction Alkynes Alkyl halides. Nucleophilic substitution (SN1 and SN2 mechanisms) and elimination (E1 and E2 mechanisms) reactions.

Alcohols, ethers and epoxides. Thiols and their derivatives. Aldehydes and Ketones and their derivatives: addition of water, cyanides, aldolic condensation, Cannizzaro reaction, reaction with Grignard reagents, reactions with ammonia derivatives (formation of imines, enamines, oxymes, hydrazones, acetals, ketals, cyanohydrins). Wittig reaction. Keto-enol tautomerism: enols and enolates, aldol condensation. Carboxylic acids and their derivatives: esters, acyl halides, anhydrides, amides, nitriles, ketenes. Nucleophilic acyl substitution, Claisen condensation. Acetacetic and malonic ester synthesis. Michael addition reaction. Amines: general characteristics – basicity, amine synthesis (ammonia alkylation), Hinsberg test, Hofmann rearrangement, reactions with nitrous acid.

Type of didactic activities: Lectures and practical course

:

Texts and teaching materials: Organic Chemistry, Structure and Function, P. Vollhardt, N. E. Schore, 7th Ed., W.H. Freeman & Co.

Verification of learning skills: Final written examination consisting in a variable number (10 in average) of exercises including assignement of the correct nomenclature, guided synthesis, functional group interconversion, open questions (mark: 30) Oral examination consisting in a variable number (5 in average) of questions aimed at verifying the comprehension of the principles and reactivity of organic chemistry (mark 30) Final mark: average of the written and oral examination.

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