ORGANIC CHEMISTRY II

Università degli Studi
"G. d'Annunzio"

Chieti - Pescara

General Module

Course Sheet

Course code:

00218II

Academic Year of enrolment:

2021

Year of supply:

2023/2024

Type of Course:

Basic

Degree:

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

Disciplinary Sector:

Organic Chemistry

Is part of:

ORGANIC CHEMISTRY II

Location:

CHIETI

Credits:

Programme Year:

Professor and Collaborators:

SIANI Gabriella

Cycle:

First semester

Obligatory attendance:

Yes

Hours of classroom activity:

Individual study hours:

115

Prerequisites:

Students must have acquired the skills covered by the Organic Chemistry I course, for which he must have passed the exam. They must be familiar with the functional groups, the mechanisms of reactions such as nucleophilic and electrophilic substitutions, electrophilic and nucleophilic additions, the concepts of stereochemistry (enantiomers, diastereomers, mesoforms) and acid-base equilibria.

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

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 - 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.
• Organosulfur compounds: Thiols, disulfides, sulfoxides and sulfones - Chiral sulfoxides - Sulfonium salts - Thioesters - Sulfenic, sulfinic and sulfonic acids and their derivatives

Recommended Bibliography

• W.H. Brown - Chimica Organica, ed. Edises
• Marc Loudon - Chimica Organica, ed. Edises
• Bruno Botta - Chimica Organica. ed. edi-ermes

Teaching Methods

The course consists of 48 hours of theoretical lessons (6 CFU) and 12 hours of exercises (1 CFU). Each theoretical topic will be completed by classroom exercises. 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 5 open-ended questions (+ 1 question relating to the part of pericyclic reactions) with theoretical questions (and/or simple exercises) covering the entire programme. Each answer is worth a maximum of 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 in carrying out 4 exercises (+ 1 exercise relating to the part of the pericyclic reactions). 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 higher than 10, the final grade of the exam is given by the sum of the scores achieved in the two written tests unless an oral test is requested by the teacher or the student. The required oral test constitutes a further element of evaluation and the final grade will be established taking into account both the scores achieved in the written tests and in the oral test. It is important to underline that the oral test should not be understood as aimed at raising the grade obtained in the writings but, in the event of a negative result, the grade may be lowered even to determine the rejection.
If the sum of the marks obtained in the tests is equal to 32, honors will be assigned (30L).
During the exam it is not allowed to consult books, notes or electronic devices

Contacts/More Information

Prof. Siani 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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