ORGANIC CHEMISTRY II

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

Single discipline educational activity

Course Sheet

Course code:

00218

Academic Year of enrolment:

2020

Year of supply:

2022/2023

Type of Course:

Basic

Degree:

Course of Single Cycle Degree 5 years in MEDICINAL CHEMISTRY AND PHARMACEUTICAL TECHNOLOGY

Disciplinary Sector:

Organic Chemistry

Language:

Italian

Location:

CHIETI

Credits:

Programme Year:

Professor and Collaborators:

SIANI Gabriella

Cycle:

First semester

Obligatory attendance:

Yes

Minimum hours of attendance:

Hours of classroom activity:

Individual study hours:

153

Prerequisites:

ORGANIC CHEMISTRY I

Objectives

The aim of the course is to provide the student with more advanced knowledge on the structure and reactivity of organic compounds, with particular regard to the most modern synthetic strategies. Topics such as supramolecular chemistry, organic reactions catalyzed by transition metals, phase transfer catalysis and other topics that have been particularly researched in recent years are addressed. The ability to deal with problems related to the design and synthesis of organic compounds is stimulated and developed

Contents

• Hydrocarbons
• Halogenated organic compounds
• Heterocyclic compounds
• Organometallic compounds
• Radical reactions of organotin compounds.
• Carbenes, nitrenes and nitrenium ions
• Oxygenated organic compounds
• Polyfunctional compounds, lipids and surfactants
• Organic nitrogen compounds
• Organosulfur compounds
• Pericyclic Reactions and Rearrangement reactions

Extended Syllabus

• Hydrocarbons: Reaction of alkanes with super acids – Alkenes: alkoxymercuriation; oxydrilation; ozonolysis; hydroboration-oxydation- Stereospecific reductions of alkynes - Mono-electronic reduction of alkynes by solutions of metals in liquid ammonia - Polyenes: 1,4 addition reaction of conjugated dienes- The Birch reaction of arenes - The Diels-Alder reaction - Allenes - [2+2] photodimerization reactions - Electrocyclic reactions - Aromatic polycyclic hydrocarbons.
• Halogenated organic compounds: Vinyl halides, halo arenes, allylic halides, benzyl halides - Nucleophilic aromatic substitution reactions - Aryne intermediates - Radical nucleophilic aromatic substitution reaction.
• Heterocyclic compounds: Resonance energy of aromatic heterocycles with one heteroatom - Relative reactivity - Orientation of electrophylic aromatic substitution reactions - Basicity and molecular structure - Nucleophilic substitution reactions of pyridine - Pyridine-N-oxide - Heterocycles with more than one heteroatoms.
• Organometallic compounds: Generality - Grignard reagents: use in the organic synthesis - Cadmium organic reagents - Organocopper reagents - Reformatsky reaction –Ullman reaction; biphenyls and biphenyl stereochemistry - Transition metal coordination complexes in homogeneous catalysis - Heck reaction - Suzuki reaction - Metallocenes.
• Radical reactions of organotin compounds.
• Carbenes, nitrenes and nitrenium ions: Structure, formation and properties - Reactivity - Addition and insertion reactions - Carbenoid reagents - Acyl nitrenes.
• Oxygenated organic compounds: Epoxides: synthesis and reactivity – Regiochemical/stereochemical aspects of ring-opening reactions - Other cyclic ethers - Crown ethers - Phenol, salicylic acid and derivatives - Reactivity of the alpha hydrogens of carbonyl compounds - Enols and enolates - Enamines - Alpha-beta unsaturated carbonyl compounds: conjugate additions; Michael addition - Phosphorus and sulphur ylides - Wittig reaction.
• Polyfunctional compounds, lipids and surfactants: Dicarboxylic acids - unsaturated acids, hydroxy acids and lactones - Macrocyclic lactones - Keto acids - Fats, oils, soaps, waxes and phosphoglycerides - Phase transfer catalysis.
• Organic nitrogen compounds: Reduction of nitro compounds - Hofmann degradation reaction – Hofmann elimination reaction - Cope elimination reaction - Azides, nitrones, nitrile oxides - 1,3-dipolar cycloadditions.
• Organosulfur compounds: Thiols, disulfides, sulfoxides and sulfones - Chiral sulfoxides - Sulfonium salts - Thioesters - Sulfenic, sulfinic and sulfonic acids and their derivatives.
• Rearrangement reactions: Allylic, benzilic and pinacol rearrangements - Benzidine rearrangement - Migratory aptidude - Curtius, Claisen and Cope rearrangements - Ester pyrolysis - Hydroperoxide decomposition - Favorskii, Wolff and Beckmann rearrangements - Baeyer-Villiger oxidation.

Recommended Bibliography

• R. Macomber, Chimica Organica, ed. Zanichelli, Bologna
• Clayden et al – Fondamenti di Chimica Organica, ed. Zanichelli, Bologna
• Marc Loudon –Chimica Organica, ed. Edises

Methods of Provision

Conventional

Teaching Methods

The course consists of 72 hours of frontal teaching. Each theoretical topic will be enriched with exercises in the classroom dedicated to the carrying out of exercises that will follow the topics of the lessons. The exercises will in part be carried out on the blackboard by the teacher, in part they will require the active participation of the students

Evaluation methods

Verification of learning:

The exam consists of two written tests.
The first written test, lasting 90 minutes, consists of 6 open-ended questions with theoretical questions (and / or simple exercises) covering the entire program. Each answer is worth max 2 points and the maximum score achievable is, therefore, equal to 12. If the score is equal to or greater than 8 the exam continues and the student is admitted to the second written test.
The second written test, of the traditional type and lasting 100 minutes, consists of 5 exercises. This test allows you to achieve a maximum score of 20. If the score is less than 10, the test is considered insufficient. If the score is more than 10, the final mark of the exam is given by the sum of the scores obtained in the two written tests unless an oral exam is requested by the teacher or student.
The optional oral part covers all the topics of the course.and constitutes an additional element of evaluation and the final mark will be established taking into account both the scores obtained in the written tests and the oral test. It is important to underline that the oral examination should not be understood as aimed at raising the score obtained in the writings and, in the case of a negative result, the score may be lowered even to the point of rejection.
If the sum of the marks obtained in the tests will be equal to 32, the final mark is 30 with honor (30L).
During the examination it is not allowed to consult books, notes or any kind of electronic devices

Contacts/More Information

The teacher receives the students every day by appointment to be agreed by e-mail

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

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