Ateneo - UPO

Provide the student with the basic operations of synthetic organic chemistry. See “Programma esteso” (Extended Program) for more detailed information.

Carey, Sundberg, "Advanced Organic Chemistry", Plenum Press ed.
Clayden and al. "Organic Chemistry" Oxford University Press ed.

Comprehension skills: knowledge of the basic reactions of synthetic organic chemistry. Ability to work in an organic chemistry lab. Strictness in the scientific work.
Applying the knowledge: to be able to properly fill in the laboratory notebook. Critical comprehension of the observed behaviour of the chemical reactions performed in the lab.

Organic Chemistry I and its Laboratory.

The course features a series of laboratory experiences, where the students are divided in groups of two. At the beginning, the teacher will provide a written trace of the reaction to be performed. The information given is essential, and the pupils shall themselves find out the mechanism and the expected products of the reaction. The students will discuss among them the above issues, and at the end, one of them will come to the blackboard to explain the reaction details, in agreement with the knowledge acquired in the previous courses of organic chemistry (1 and 2). After the end of each reaction, the students will illustrate the development of the reaction itself, in particular if it yielded the expected products or not, and in the latter case trying to understand the reasons why. At the end of the lab, the students must carry out a bibliographic search about a historically significant reaction of organic chemistry. The pupils are taught how to correctly do such a research: trying to understand the innovative meaning of the reaction, as well as the limits and the application field of the novel method.

The learning is checked at the beginning of each laboratory session: a student is called to the blackboard and asked to explain in detail the reaction of the previous day, highlighting the key steps, the mechanism and the results obtained. The discussion is collective: the other students are required to participate to the discussion.

At the end of the course, the students shall bring the lab notebook to the teacher, correctly compiled for every experience carried out.
The examination will feature at least three open questions concerning the reactions performed in the lab, as to evaluate the students' communication skills, and both her/his theoretical and practical knowledge.
In addition, each of them has to perform a bibliographic search upon a historically significant reaction of organic chemistry.

Aldol condensation: auto-condensation of a methylketon under both acidic and basic conditions; crossed condensation of a keton and a non-enolizable aldehyde. Additions to carbonyl: preparation of a Grignard reagent and its addition to an aldehyde (Wittig). Electrophilic aromatic substitutions: synthesis of crataegon. Elimination reactions (E1): synthesis of an olefin starting from a tertiary alcohol.
How to fill in the laboratory notebook.
How to browse the on-line scientific literature, and how to carry out the study case (literature search).

1. Knowledge and comprehension skills: the understanding of the basic reactions of synthetic organic chemistry is the main goal of this course. Moreover, both the theoretical, and the practical knowledge of how to operate in an organic lab, are required.
2. Ability to apply one's own comprehension and knowledge:
the student will have to demonstrate her/his knowledge of the basic reactions of synthetic organic chemistry, and in addition, to be able to apply the the acquired knowledge to lab operativity.
The student shall also be able to apply the above theoretical learnings to everyday laboratory practice. Hence, it is expected that he/she will be able to operate autonomously in the organic laboratory. Finally, the ability to fill in the lab notebook is requested.
3. Communication skills: the student will have to carry out the bibliographic search autonomously, demonstrating a correct exposition of the bibliographic search, demonstrating to possess an adequate scientific language.
4. Judgement ability: the pupil shall know how to discriminate among apparently equal synthetic pathways, thus showing a deep comprehension of the investigated reaction.
5. Learning abilities: they will be evaluated as the to face autonomously the study case (i.e., the bibliographic search).