Organic Chemistry 1

A.Y. 2019/2020
10
Max ECTS
88
Overall hours
SSD
CHIM/06
Language
Italian
Learning objectives
The objectives of the Organic Chemistry 1 course are aimed at the learning, by the student, of the fundamental principles of organic chemistry: from the nature of chemical bonds to the molecular structure, from the shape of the molecules to the stereochemistry up to the study of the reactivity of the organic compounds based on the nature of their functional groups. Therefore, the ability to recognize functional groups, the understanding of reaction mechanisms and the critical evaluation of related stereochemical aspects are the fundamental objectives of teaching. The purpose of this course is to provide a reasoning method to facilitate the learning of the basic notions. In this regard there will be numerous examples of practical application of the concepts taught and the lessons will be accompanied by exercises on the blackboard with the aim of deepening and assimilating the topics covered in the theoretical lessons.
Expected learning outcomes
At the end of the course, students must be able to: - acquire the appropriate terminology to name the molecules and describe their reactivity; discuss the mechanisms of organic reactions applied to specific substrates; propose synthetic routes for the construction of simple organic molecules; - possess the ability to present their knowledge in a clear and orderly manner, with appropriate scientific language and with rigorous arguments.
Course syllabus and organization

Linea AK

Responsible
Lesson period
year
Course syllabus
Chemical bonding and structure: Ionic and covalent bonds; polarity. Structures and formulas of organic molecules. Resonance structures. Acid-base equilibrium. Functional groups in organic chemistry.
Alkanes. Naming, conformational isomerism, Newman projections, kinetics and thermodynamics of conformational isomerism. Reactions of alkanes. Alogenation, alkyl radicals, hyperconiugation. Combustion. Cyclic alkanes. Naming; ring strain. Substituted cycloexanes and conformational considerations.
Stereochemistry. Chiral molecules; optical activity; absolute configurations and R-S sequence rules; Fischer projections. Molecules with several stereocenters: diastereomers and meso compounds. Stereochemistry in chemical reactions; resolution of enantiomers.
Haloalkanes. Naming. Nucleophilic substitution SN2 and SN1: kinetics, stereochemistry, leaving group ability, solvent effects, relative stability of carbocations. Elimination reactions E1 and E2. Organometallic compounds: preparation and reactivity.
Alcohols. Naming. Alcohols as acids and bases. Synthesis by nucleophilic substitution or organometallic reagents. Alkoxide. Oxidations.
Ethers. Naming, synthesis and reactivity.
Alkenes. Naming, structure and E/Z isomerism; relative stability and heat of hydrogenation. Synthesis and reactivity. Synthesis and reactivity of oxiranes.
Alkynes. Naming, acidity. Synthesis and reactivity.
Delocalized systems. Allylic system and conjugated dienes. Diels-Alder reaction. Benzene and aromaticity.
Aldehydes and ketones. Naming, structure of carbonyl group. Synthesis. Reactions of nucleophilic additions; oxidations and reductions.
Carboxylic acids and derivatives. Naming and acidity. Synthesis and reactivity. Dicarboxylic acids. Esters, anhydrides, acid chlorides, amides, nitriles.
Alkylamines. Naming. Basicity. Synthesis and reactivity.
Carbohydrates. Structures, classification, configuration. Mutarotation. Reactivity.
Prerequisites for admission
The course is aimed at students who have acquired General Chemistry knowledge.
Teaching methods
The lessons take place in the first semester of the academic year and in part of the second semester. Slides are provided in which the student finds a trace of the topics covered during the lessons. Exercises are also carried out on the blackboard in which gradually more complex exercises are solved up to the typical typology of the written examination.
Teaching Resources
Some didactic texts are recommended including:
P. Y. Bruice - Chimica Organica 3°ediz. it. su 8° ediz. amer. - Ed. Edises - 2017
W.H. Brown et al. - Chimica Organica 5°ediz. it. - Ed. Edises - 2015
J. Mc Murry - Chimica Organica - ediz. it. su 8° ediz. ingl. - Ed. Piccin - 2012
M. Loudon - Chimica Organica - ediz. it. su 5° ediz. amer. - Ed. Edises - 2010
Assessment methods and Criteria
There are two ongoing tests which, if both sufficient, are valid as a written test. The exam consists of a written and an oral test. Written test: 10 exercises (practical applications of the theory) to be carried out in two hours. Each correct exercise allows the acquisition of a score between zero and three points. Successful completion of the written test, and therefore admission to the oral test, is achieved upon the overall achievement of 18 points. Oral exam: it takes place after the time necessary for the correction of the writings, on average starting from one week from the written exam, and concerns the theoretical topics covered by the course and basis of the exercises proposed in the written exam. The final mark is formulated by the teacher, evaluating the student's overall preparation.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 10
Practicals: 16 hours
Lessons: 72 hours
Professor: La Rosa Concetta

Linea LZ

Responsible
Lesson period
year
Course syllabus
Chemical bonding and structure: Ionic and covalent bonds; polarity. Structures and formulas of organic molecules. Resonance structures. Acid-base equilibrium. Functional groups in organic chemistry.
Alkanes. Naming, conformational isomerism, Newman projections, kinetics and thermodynamics of conformational isomerism. Reactions of alkanes. Alogenation, alkyl radicals, hyperconiugation. Combustion. Cyclic alkanes. Naming; ring strain. Substituted cycloexanes and conformational considerations.
Stereochemistry. Chiral molecules; optical activity; absolute configurations and R-S sequence rules; Fischer projections. Molecules with several stereocenters: diastereomers and meso compounds. Stereochemistry in chemical reactions; resolution of enantiomers.
Haloalkanes. Naming. Nucleophilic substitution SN2 and SN1: kinetics, stereochemistry, leaving group ability, solvent effects, relative stability of carbocations. Elimination reactions E1 and E2. Organometallic compounds: preparation and reactivity.
Alcohols. Naming. Alcohols as acids and bases. Synthesis by nucleophilic substitution or organometallic reagents. Alkoxide. Oxidations.
Ethers. Naming, synthesis and reactivity.
Alkenes. Naming, structure and E/Z isomerism; relative stability and heat of hydrogenation. Synthesis and reactivity. Synthesis and reactivity of oxiranes.
Alkynes. Naming, acidity. Synthesis and reactivity.
Delocalized systems. Allylic system and conjugated dienes. Diels-Alder reaction. Benzene and aromaticity.
Aldehydes and ketones. Naming, structure of carbonyl group. Synthesis. Reactions of nucleophilic additions; oxidations and reductions.
Carboxylic acids and derivatives. Naming and acidity. Synthesis and reactivity. Dicarboxylic acids. Esters, anhydrides, acid chlorides, amides, nitriles.
Carbohydrates. Structures, classification, configuration. Mutarotation. Reactivity.
Alkylamines. Naming. Basicity. Synthesis and reactivity.
Prerequisites for admission
The course is delivered to students that have acquired competences in General Chemistry
Teaching methods
theoretical lessons and exercises
Teaching Resources
P. Y. Bruice - Chimica Organica 3°ediz. it. su 8° ediz. amer. - Ed. Edises - 2017
W.H. Brown et al. - Chimica Organica 5°ediz. it. - Ed. Edises - 2015
J. Mc Murry - Chimica Organica - ediz. it. su 8° ediz. ingl. - Ed. Piccin - 2012
M. Loudon - Chimica Organica - ediz. it. su 5° ediz. amer. - Ed. Edises - 2010
Slides provided by the teacher and uploaded on ARIEL webpage
Assessment methods and Criteria
The examination consists of a written and an oral test.
Concerning the written test, students can choose between 1) two ongoing verifications which, if both passed, are valid as the final written test; 2) only one written test at the end of the course.
- Written exam: 10 exercises to be carried out in two hours. Each exercise requires the acquisition of a score between zero and three points. The passing of the written test, and therefore the admission to the oral test, is achieved upon reaching a total of 18 points.
- Oral test: it takes place after the time necessary for the correction of the written test, (approximately after one week) and concerns the theoretical topics covered by the course The final grade is formulated by the teacher evaluating the overall preparation and the competences acquired
CHIM/06 - ORGANIC CHEMISTRY - University credits: 10
Practicals: 16 hours
Lessons: 72 hours
Professor: Clerici Francesca