00148 - Organic Chemistry

Learning outcomes

At the end of the course, the student acquires the basic notions on the structure and properties of organic compounds, with particular regard to natural organic substances and those of biochemical interest. Based on the reactivity of the main functional groups, it is able to trace the synthesis of new compounds. It deepens the topics covered through exercises, applied experimentally in the course of practical exercises in the laboratory. At the end of the laboratory, the student has the technical-practical knowledge to perform synthesis reactions, including the recognition of organic compounds.

Course contents

The following topics covered in the General and Inorganic Chemistry module are prerequisite knowledge and are required:

Electronegativity and Chemical Bonding

Electronegativity and chemical bonding. Lewis bonding model. Lewis structures of ions and covalent molecules. Formal charge. Exceptions to the octet rule. Bond angles and molecular geometry. Functional groups. Structural isomers. Resonance theory. Shape of atomic orbitals. Valence bond theory and covalent bonding. Formation of a covalent bond through overlap of atomic orbitals. Hybridization of atomic orbitals. Molecular orbital approach to covalent bonding. Formation of molecular orbitals.

Acids and Bases. Acids and bases. Brønsted–Lowry acids and bases. Quantitative measurement of acid and base strength. Equilibrium position in acid–base reactions. Lewis acids and bases.

 
Alkanes and Cycloalkanes

Structure of alkanes. Structural isomerism of alkanes. Alkane nomenclature. The IUPAC system. Common names. Classification of carbon and hydrogen atoms. Cycloalkanes: structure and nomenclature. Bicyclic alkanes. Conformations of alkanes and cycloalkanes. Cyclohexane. Cis–trans isomerism in cycloalkanes. Physical properties of alkanes and cycloalkanes. Reactions of alkanes: oxidation; halogenation. Regioselectivity. Exercises.

Alkenes, Alkynes, and Addition Reactions

Alkenes. Nomenclature. IUPAC names and common names. Structure. Valence bond approach. Bond length and bond strength in alkanes, alkenes, and alkynes. Molecular orbital description of the C=C bond. Cis–trans isomerism. E–Z nomenclature. Cycloalkenes. Cis–trans isomerism in cycloalkenes. Cis–trans isomerism in dienes, trienes, etc. Physical properties. Overview of preparation reactions. Reaction mechanisms. Electrophilic additions. Bromination. Addition of hydrogen halides. Addition of water: acid-catalyzed hydration. Formation and stability of carbocation intermediates. Regioselectivity. Oxidation with peracids. Oxidation with permanganate. Catalytic reduction. Alkynes. Introduction to structure, IUPAC nomenclature, common names, physical properties, acidity, preparation, and reactions.

Conjugated Dienes and Conjugated Systems

Conjugated dienes/conjugated systems. Nomenclature. Stability. Structure. Valence bond model. Molecular orbital model. Electrophilic additions. Conjugate addition: 1,2-addition and 1,4-addition. Exercises.

Chirality and Stereoisomerism

Chirality as a geometric property. Chirality arising from a stereocenter. Stereocenters other than carbon. Classification of stereoisomers, diastereomers, and enantiomers. R–S system. Fischer projections. Optical activity and polarimetry. Racemic mixtures. Optical purity and enantiomeric excess. Molecules with two or more stereocenters. Meso compounds. Cyclic molecules with two or more stereocenters. Properties of stereoisomers. Resolution of enantiomers. Exercises.

Alkyl Halides, SN Substitutions, and E Eliminations

Structure. Nomenclature, IUPAC system, common names. Physical properties. Polarity. Preparation. Conversion of alcohols into alkyl halides. Halogenation of alkanes. Addition of HX to alkenes. Reactions with bases and nucleophiles. Aliphatic nucleophilic substitution. Mechanisms of aliphatic nucleophilic substitution. Relative nucleophilicity. Polar aprotic and polar protic solvents. Stereochemistry. SN1 reactions. SN2 reactions. Structure of alkyl halides. Leaving groups. E1 reactions. E2 reactions. Exercises.

Alcohols and Thiols; Ethers and Epoxides

Structure of alcohols and thiols. Nomenclature. Physical properties. Preparation of alcohols. Acid-catalyzed hydration of alkenes. Reactions of alcohols. Acidity of alcohols. Basicity of alcohols. Conversion into alkyl halides. Dehydration of alcohols to alkenes. Oxidation of primary and secondary alcohols. Reactions of thiols. Acidity.

Structure of ethers. Ether nomenclature. Physical properties of ethers. Preparation. Williamson ether synthesis. Acid-catalyzed addition of alcohols to alkenes. Acid-catalyzed dehydration of alcohols. Epoxides. Structure and nomenclature. Synthesis. Reactions of epoxides. Acid-catalyzed ring opening. Nucleophilic ring opening. Exercises.

Aromatic Compounds, Benzene, and Electrophilic Aromatic Substitution

Structure of benzene. Kekulé model. Valence bond model. Resonance energy of benzene. Concept of aromaticity. Hückel's rule. Heteroaromatic compounds. Electrophilic aromatic substitution. Bromination and chlorination. Nitration and sulfonation. Friedel–Crafts alkylation and acylation. Effect of substituents on further substitution. Activating/deactivating effects and ortho-, meta-, para-directing effects. Exercises.

Aldehydes and Ketones: Addition Reactions

Structure. Structural characteristics. Covalent bonding. IUPAC nomenclature. Common names. Physical properties. Preparation. Oxidation of primary and secondary alcohols. Overview of preparation reactions. Reactivity. Nucleophilic addition. Organometallic compounds. Addition of Grignard reagents. Addition of water. Addition of alcohols: formation of hemiacetals and acetals. Acetals as protecting groups. Addition of nitrogen nucleophiles. Schiff bases. Ammonia and its derivatives. Keto–enol tautomerism. Acidity of α-hydrogens. Reactions at the α-carbon. Oxidation of aldehydes. Oxidation of ketones. Catalytic reduction. Reduction with boron and aluminum metal hydrides. Exercises.

Carbohydrates

Monosaccharides. Structure. Nomenclature. Stereoisomerism. Cyclic structure of monosaccharides. Glucose, ribose, fructose. Fischer projections. Haworth projections. Mutarotation. Physical properties. Reactions of monosaccharides. Formation of glycosides. Disaccharides, maltose, etc. Reduction. Oxidation. Polysaccharides. Structure of nucleosides and nucleotides in nucleic acids. Introduction to RNA and DNA. ATP and NADH. Exercises.

Carboxylic Acids

Structure. Nomenclature. IUPAC system. Common names. Physical properties. Acidity. Acid ionization constants. Reactions with bases. Preparation. Oxidation of primary alcohols. Oxidation of aldehydes. Reduction. Lithium aluminum hydride. Esterification. Fischer esterification. Conversion into acyl halides. Exercises.

Carboxylic Acid Derivatives and Acyl Nucleophilic Substitution

Structure and nomenclature. Acyl halides, anhydrides, esters, amides (nitriles). Characteristic reactions: acyl nucleophilic substitution. Analysis of leaving groups. For all classes: reaction with water, hydrolysis. Reaction with alcohols. Reactions with ammonia and amines. Reductions. Reactions with Grignard reagents. Exercises.

Lipids

Fatty acids, structure of fatty acids. Triglycerides. Structure and preparation of natural soaps. Phospholipids. Introduction to fatty acid biosynthesis. Exercises.

Amines

Structure and classification. Nomenclature. IUPAC names and common names. Chirality of amines and quaternary ammonium ions. Physical properties. Basicity. Preparation. Alkylation of ammonia and amines. Reduction of nitro groups to primary amino groups. Gabriel synthesis of primary alkylamines. Reductive amination of aldehydes and ketones. Reactions of amines. Reactions of tertiary aliphatic amines.

Amino Acids and Peptides

Amino acids. Structure. Chirality of amino acids. Proteinogenic amino acids. Acid–base properties. Asymmetric synthesis of amino acids. Polypeptides and proteins. Primary structure of polypeptides and proteins, conformational aspects. The peptide bond. Peptide synthesis in solution and by the Merrifield method. Protection/deprotection and activation strategies. Examples of peptides in medicinal chemistry. Exercises.

Enolate Anion Chemistry and C–C Bond-Forming Condensation Reactions

Acidity at the α-carbon of carbonyl compounds. Structure of the enolate anion. Aldol condensation. Crossed aldol condensation. Claisen condensation. Crossed Claisen condensation. Intramolecular condensations leading to cyclic structures. Acetoacetic ester synthesis of ketones. Decarboxylation of keto acids. Malonic ester synthesis of carboxylic acids. Decarboxylation of dicarboxylic acids. Conjugate addition.

 

Readings/Bibliography

Both introductory/fundamentals texts (abridged versions) and comprehensive textbooks are listed. The comprehensive texts may also be useful for subsequent courses in biochemistry. Some of these books include molecular model kits that are particularly helpful for visualizing and studying molecules in three dimensions.

Introduction to Organic Chemistry with Molecular Models, William H. Brown & Thomas Poon, EdiSES.

Organic Chemistry with Molecular Models, W.H. Brown, B.L. Iverson, E.V. Anslyn & C.S. Foote, EdiSES.

Fundamentals of Organic Chemistry, John McMurry, Zanichelli.

Organic Chemistry, John McMurry, Piccin.

Organic Chemistry, T.W. Graham Solomons & Craig B. Fryhle, Zanichelli.

Organic Chemistry (with digital content), Peter C. Vollhardt & Neil E. Schore, Zanichelli.

Teaching methods

Lectures, with ongoing formative assessments and group work on problem-solving exercises.

Midterm written assessments, followed by in-class review and discussion of solutions.

Individual and group exercises carried out during class.

Students with Specific Learning Disabilities (SLD) or Temporary/Permanent Disabilities. Students with specific learning disabilities (SLD) or temporary or permanent disabilities are requested to contact the University's designated support office in advance (https://site.unibo.it/studenti-con-disabilita-e-dsa/it ). The office will propose any appropriate accommodations, which must be submitted to the course instructor for approval at least 15 days in advance. The instructor will evaluate the proposed accommodations in relation to the course learning objectives.

Assessment methods

Organic Chemistry Module: Oral examination. The examination begins with the solution of a problem on the board, based on supporting teaching materials that are shared and made available through the course portal. The second part of the examination focuses on the theoretical concepts related to the problem just completed, together with any relevant connections to other topics covered in the course.

Laboratory Module: Students are required to submit a brief laboratory report on one of the experiments performed during the laboratory sessions. The report must be submitted sufficiently in advance of the examination. It will be reviewed by the instructor, and any comments or feedback will be communicated to the student. During the examination, the report will be discussed to assess the student's understanding of the concepts underlying the laboratory procedures and experiments.

The final examination grade is based on: 40% discussion of the problem-solving exercise; 40% assessment of theoretical knowledge; 20% discussion of the laboratory report.

Each examination typically lasts approximately 25 minutes. Upon request, the examination may be conducted in English.

Students with Specific Learning Disabilities (SLD) or Temporary/Permanent Disabilities. Students with specific learning disabilities (SLD) or temporary or permanent disabilities are requested to contact the University's designated support office in advance.

Use of Artificial Intelligence. Limited and non-substantive use of artificial intelligence is permitted for support activities such as summarization and text rephrasing.

 

Teaching tools

power point projections, handouts and laboratory exercises guide available on unibo's "Online Teachings" platform. Solid molecular models of atoms and molecules and virtual models. Presentation of movies, animations, 3D simulations

Office hours

See the website of Luca Gentilucci

See the website of Giulio Bertuzzi

See the website of Giulio Bertuzzi