ORGANIC CHEMISTRY 1

Degree course: 
Corso di First cycle degree in CHEMICAL AND INDUSTRIAL CHEMISTRY
Academic year when starting the degree: 
2021/2022
Year: 
1
Academic year in which the course will be held: 
2021/2022
Course type: 
Basic compulsory subjects
Credits: 
9
Period: 
Second semester
Standard lectures hours: 
96
Detail of lecture’s hours: 
Lesson (72 hours), Exercise (24 hours)
Requirements: 

Students are familiar with the principle of general chemistry and in particular with the theory of valence bond, chemical equilibrium and the concept of acidity and basicity according to Broensted-Lowry and Lewis.

Final Examination: 
Orale

Final written examination consisting of a variable number (8-10) of exercises comprising nomenclature and absolute configuration determination, functional group interconversion, conformational analysis, multi-step synthesis.
Oral examination consistiong in a variable number of questions aimed at evaluating the comprehension of organic chemistry principle and reactivity.

Assessment: 
Voto Finale

The course will provide students of the BSc in Chemistry and Industrial Chemistry with a basic knowledge of organic chemistry and in particular of the following topics:
- Organic Nomenclature based on IUPAC rules
- Mechanisms of organic reactions
- Functional groups and their interconversion

By the end of this course students willl be able to:
- Devise synthetic paths for the construction of simple organic molecules
- Discuss mechanistic details of organic transformations applied to specific substrates
- adopt the correct terminology to name organic molecules and describe their reactivity

Introduction to Organic Chemistry (historical notes and varieties of organic molecules). Atomic Orbitals, hybridization, ionic and covalent bonds, molecular orbitals
Electronegativity and bond polarization. Non bonding interactions, Inductive and resonance effects
Acids and bases in organic chemistry
Main functional groups, their nomenclature and reactivity
Nucleophiles and electrophiles, Carobocations and their transpositions, carbanions and radicals
Principles of organic stereochemistry (molecular symmetry, chirality, stereocentres, absolute and relative configuration descriptors)
Alkanes and cycloalkanes: structure and nomenclature. Concformational analysis of open chains
alkenes and polyenes: geometric isomerism and electrophilic addition (regioselectivity, spereospecificity and stereoselctivity)
Addition of strong and weak acids, alogens, hydroboration, oxymercuriation, oxidation. Reactivity of conjugate dienes: 1,4-addition, Diels-Alder reaction.
Alkynes
Alogenoalkanes: Nucleophilic substitution reaction (Sn1 and Sn2) and elimination (E1 and E2)
Alcohols, ethers and epoxides.
Aldehydes, ketones and their derivatives: addition of water, alcohols, cyanides, cyanides. Addition of Grignard reagents. Reactions with ammonia derivatives: imines, enamines, oxymes, hydrazones, acetals, ketals and cyanohydrins. Wittig reactions. Keto-enol tautomerisation: enols, enolates and aldol condensation.
Carboxylic acids and their derivatives: esters, acyl halides, anhydrides, nitriles, amides. Acylic nucleophilic substitution. Claisen condensation, Acetacetic and malonic synthesis. Michael addition

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Several texts of Organic Chemistry can be taken as a reference for the study of the subject. The development of the course foresees to draw from different sources without rigidly considering the adoption of a single textbook. We recommend the use of one of the following texts (both in Italian and in English):

W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote - Organic Chemistry - Edises (Sixth Edition)

T. W. G. Solomons, C. B. Fhryle, S. A. Snyder - Organic Chemistry - Wiley (12th Edition)

P. Y. Bruice - Organic Chemistry - Edises (Third Edition)

K. P. C. Vollhardt, N. E. Schore, Organic Chemistry, 4th Italian Ed., Zanichelli

D. Klein - Organic Chemistry - Wiley (3rd Edition)

J. McMurry - Organic Chemistry - Cencage (9th Edition)

L. G. Wade, J. W. Simek - Organic Chemistry - Pearson (9th Edition).

F. A. Carey, R. M. Giuliano - Organic Chemistry - McGrawHill (10th Edition)

Texts for further consultation is the following:

J. Clayden, N. Greeves, S. Warren - Organic Chemistry - Oxford University Press (2nd Edition)

M. B. Smith - Organic Chemistry: an Acid-Base Approach - CRC Press (2nd Edition)

Recommended texts for carrying out exercises in Organic Chemistry:

T. W. G. Solomons, C. B. Fryhle, R. G. Johnson -
Organic Chemistry through exercises -
Zanichelli

M. V. D'Auria, O. Taglialatela Scafati, A. Zampella -
Reasoned Guide to the development of Organic Chemistry exercises - Loghia

P. C. Vollhardt, N. E. Schore - Organic chemistry. Solved Organic Chemistry Exercises -
Zanichelli

F. Nicotra, L. Cipolla - Organic chemistry exercise book - Edises

Convenzionale

72 lecture hours and 24 hours of practicals

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Professors

SISTI MASSIMO