ORGANIC CHEMISTRY 1
- Overview
- Assessment methods
- Learning objectives
- Contents
- Delivery method
- Teaching methods
- Contacts/Info
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.
The learning assessment can be done through two different ways. Students can choose to take a single final exam at the end of the course or three partial exams that will be held during the semester on an agreed day and during class time.
The single final exam consists of a variable number (typically 12/13) of exercises divided between: recognition of functional groups, assignment of the correct nomenclature and stereochemistry, exercises on chirality, interconversions of functional groups, conformational analysis exercises, multi-step synthesis. Passing the single written exam and the related admission to the oral exam is achieved with a minimum score of 15/30. With a score between 15/30 and 18/30, admission to the oral exam occurs with reservations. The oral exam consists of a variable number of questions aimed at verifying the degree of understanding of the nomenclature, principles, reactivity and organic synthesis. The subject of the oral exam discussion will also be the reaction mechanisms illustrated during the course. Final grade out of 30.
As regards the three partial written tests, these will focus on the parts of the program covered up to that point during the delivery of the course within the semester. In the second and third partial tests, questions may obviously also be presented relating to topics covered in the test(s) previously taken. Admission to attend a subsequent partial written test occurs by passing the previous test(s) with at least a score of 15/30. At the end of the three written tests passed, the oral session of the exam will take place in which there will be a variable number of questions aimed at verifying the degree of understanding of the nomenclature, principles, reactivity and organic synthesis. The subject of the oral exam discussion will also be the reaction mechanisms illustrated during the course. Final grade out of 30.
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). Elements of atomic theory, atomic orbitals, hybridization, ionic and covalent bonds, molecular orbitals.
Electronegativity and polarity of bonds. Non-binding interactions. Inductive effects and resonance stabilization.
Acids and Bases in Organic Chemistry.
Main functional groups, their nomenclature and reactivity.
Nucleophiles and electrophiles. Carbocations and their transpositions, carbanions and radicals.
Fundamentals of organic stereochemistry (molecular symmetry, chirality, stereocenters, absolute and relative configuration descriptors).
Covalent bond and molecular geometry. Alkanes and cycloalkanes: nomenclature and structure Conformational stereoisomerism of open chains
Alkenes and polyenes: geometric stereoisomerism; electrophilic addition to alkenes; stereochemistry of addition reactions (regioselectivity, stereospecificity and stereoselectivity), addition of strong acids, weak acids, addition of halogens, hydroboration, oxymercuriation, oxidation. Reactivity of conjugated dienes: addition 1,4; Diels-Alder reaction.
Alkynes.
Alkyl halides. Nucleophilic substitution (Sn1 Sn2 mechanisms) and elimination reactions (E1, E2 mechanisms).
Alcohols, ethers, epoxides and sulphides.
Aldehydes and ketones and their derivatives: addition of water, alcohols, cyanides, reaction with Grignard's reagents, reaction with ammonia derivatives: imines, enamines, oximes, hydrazones, acetals, ketals, cyanhydrins. Wittig reaction. Organometallic compounds. Keto-enol tautomeria: enols and enolates aldol condensation.
Carboxylic acids and their derivatives: esters, acyl halides, anhydrides, amides, nitriles, Nucleophilic acyl substitution. Claisen condensation. Use of the acetacetic and malonic ester in organic synthesis. Michael addition reaction. Amines
72 lecture hours and 24 hours of practicals
The lecturer is available to more details and clarifications on any requests made by the students receiving at his office by previous contact via email: andrea.penoni@uninsubria.it or by phone (031-2386440).