55393 - Organic Chemistry

Learning outcomes

After completing this module, students learn the basic information onstructure and properties of organic compounds, with particular emphasis on natural organic compounds of biochemical interest. On the basis of the reactivity of the main functional groups, students can design the synthesis of new compounds. Topics are studied with the aid of exercises, applied experimentally in the course of a practical laboratory. At the end of the workshop, the students have the technical and practical knowledge to perform synthesis , including analysis of organic compounds.

Course contents

Introduction:  Review of structural theory, atomic orbitals, ionic bonding, covalent bonding, molecular geometry, electronegativity, molecular orbitals and acid-base theories.

Hybridization of bonds in organic compounds. Draw organic structures with correct three-dimensional geometry.  Identify bonds in a molecule as ionic or covalent. Predict the polarity of a bond. Identify the conjugate acid-base pairs in Bronsted-Lowry acid-base reactions.

Identify Lewis acids and bases.

Alkanes: Structures, nomenclature, physical properties, preparations, chemical reactions, mechanisms, carbonium ion and free radical intermediates. Draw all isomers of a given alkane molecular formula. Name alkanes by the IUPAC system. Identify carbon atoms as primary, secondary, tertiary or quarternarly. Methods of preparing alkanes. Reactions of alkanes.

Halogenation of an alkane.

Alkenes: Structure, nomenclature, physical properties, preparations, chemical reactions, mechanisms and carbocation intermediates. Name alkenes by the IUPAC system. Structures of alkenes corresponding to a given IUPAC name. Draw all the isomers of a given alkene molecule.

Differentiate between cis and trans isomers. Preparation of alkenes.  Markovnikov's Rule and “the peroxide effect”. Anti-Markovnikov's addition reaction.

Alkynes and Dienes:  Structure, nomenclature, physical properties, preparations, chemical reactions, and mechanisms. Name alkynes and dienes by the IUPAC system. Alkynes and dienes corresponding to a given IUPAC name.  Draw the molecular orbital picture of a typical alkyne and diene. Resonance and resonance energy concepts. Keto-enol tautomerization.

Cyclic Aliphatic Hydrocarbons: Structure, nomenclature, physical properties, preparations, stereochemistry, chemical reactions, mechanisms.Describe the three dimensional shapes of cycloalkanes of five carbon atoms or less.

Describe the three dimensional shapes of cycloalkanes of six carbon atoms or greater.

Locate axial and equitorial positions on cyclohexane. Identify cis and trans positions on a cyclohexane ring. Steroids.

Stereochemistry: Isomer number, optical activity, specific rotation, enantiomerism, chiral carbon, racemic modification, projections, Cahn- Ingold-Prelog (r,s) nomenclature, stereoisomers, and stereospecific reactions. Meaning of isomer number. Optical activity. Enantiomer of a given chiral compound.

Diastereoisomer of a given chiral compound. Draw chiral molecules in Newman projections.

Assign priorities to substituents around a carbon stereocenter. Assign r,s configurations to stereocenters. Decide if a stereoisomer is a meso compound.

Predict the stereochemistry of reaction products.

Mass spectroscopy, infrared spectroscopy, ultraviolet spectroscopy, nuclear magnetic resonance spectroscopy and structural determination via spectroscopy.

Aromatic Compounds - Benzene; Kekule structure, MO picture, resonance, aromatic character, Huckel's Rule, nomenclature, physical properties, chemical reactions and mechanisms. Ortho, meta and para substitution. Electrophilic aromatic substitution.

Alkyl Halides: Structure, nomenclature, physical properties, preparations, chemical reactions, Sn1, Sn2, E1, E2 mechanisms.

Mthods of synthesis for alkyl halides. Products of reactions of alkyl halides. Effects of changes in reaction conditions on substitution and elimination reactions.

Alcohols: Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and synthesis.

General structure of an alcohol. Name alcohols by the IUPAC system. Relative acidities of molecules. Synthesize alcohols.

Phenols and ethers : Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and synthesis. Acidity of phenols.

Carboxylic Acids and Derivatives: Structures, nomenclature, physical properties, preparation, chemical reactions, mechanisms, acidity, dicarboxylic acids, heteroacids, hydroxy acids, acid halides, acid anhydrides, esters and amides.

Rank compounds in order of increasing acidity. Use electronegativity and resonance arguments to predict the acidity of carboxylic acids. Synthesize aliphatic and aromatic carboxylic acids, acid halides, acid anhyhrides, esters and amides. Predict relative reactivity of carboxylic acid derivatives.

Predict the product of reactions for carboxylic acids, acid halides, acid anhydrides, esters and amides. Use nucleophilic acyl substitution reactions in synthesis. Acetoacetic ester and malonic ester methods.

Aldehydes and Ketones : Structures, nomenclature, physical properties, preparation, chemical reactions, mechanisms, condensation reactions and synthesis.

Synthesize aldehydes and ketones. Product of reactions of aldehydes and ketones. Mechanisms of nucleophilic addition reactions.

Amines : Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms, synthesis and basicity.

Carbohydrates : Definition and classifications, aldoses, ketoses, structural determination, cyclic structure, polysaccharides. Identify sugar as D or L. Draw monosaccharides in the Fischer, Haworth and Chair conformation projections. Predict the products of reactions of monosaccharides. Define the terms monosaccharide, disaccharide, reducing sugar, non-reducing sugar, anomeric center, furanose ring, pyranose ring and glucosides.

Proteins: Amino acids, peptides, classification of proteins, protein structure and

Enzymes.

Lipids: Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms, synthesis and basicity.

Nucleic acids. Nucleotides and nucleosides. DNA structure. Ribonucleic acids. Main aspects of protein synthesis.

Readings/Bibliography

Introduzione alla Chimica Organica con Modelli Molecolari, William H. Brown - Thomas Poon, EDISES

Chimica Organica - con modelli molecolari W.H. Brown – B.L. Iverson – E.V. Anslyn – C.S. Foote, EDISES

Fondamenti di chimica organica John McMurry, Zanichelli

Chimica organica di John McMurry, Piccin

Chimica organica , T W Graham Solomons, Craig B Fryhle, Zanichelli,

Chimica organica. Con Contenuto digitale (fornito elettronicamente) Copertina flessibile, Peter C. Vollhardt,‎ Neil E. Schor, Zanichelli

Teaching methods

Lessons, group-work, tests

Assessment methods

The exam is oral and integrated with the Laboratory of Chemistry. The exam begins with a exercise to be carried out on the blackboard, based onsupporting material shared and made available through the portal. The second part of the test involves the determination of theoryknowledge related to the exercise just performed. If the student has prepared reports on practical laboratorytests, we proceed to its discussion, to ensure that he/ she has fully understood the purpose of the practice. In any case, the evaluation of the reports it can not be negative, while the evaluation of the basic knowledge required for understanding the practical exercises is assessed in proportion to the credits. The final score of the examination is made for 40% of the discussion , 30% of the outcome of the discussion on theory, 20% from the discussion of tests performed in the laboratory. On average, each exam takes 30 min. At the request of the student, the test may be written in the form of processed.

Teaching tools

power-point presentation, available at Unibo/Gentilucci/materiale didattico

Solid models of atoms and molecular and virtual models.

3D simulations, movies, cartoons

Office hours

See the website of Luca Gentilucci

See the website of Andrea Gualandi

See the website of Andrea Gualandi