66687 - Organic Chemistry II and Laboratory

Learning outcomes

At the end of the course, the student will have a solid understanding of the methods and principles for the selective synthesis of organic compounds, with a particular focus on stereoselectivity. They will be proficient in selecting strategies for the use of protecting groups and choosing the most effective methods for the oxidation and reduction of organic compounds, including alternative approaches based on the principles of green chemistry. Furthermore, they will demonstrate a thorough understanding of the reactivity and synthetic methodologies related to polyfunctionalized carbonyl compounds. The student will also be well-versed in synthetic techniques involving organometallic compounds, the reactivity of organic molecules containing phosphorus, sulfur, and silicon, as well as the fundamental concepts of cycloadditions, Diels-Alder reactions, and organic free radicals. In addition, they will be able to critically evaluate synthetic pathways, analyze synthesis methods, and perform the synthesis of medium-complexity organic molecules using standard laboratory techniques. Finally, the student will be capable of monitoring the progress of organic reactions and characterizing the resulting products using common organic analysis techniques, including Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS).

Course contents

Background knowledge

All the learning outcomes of the Organic Chemistry part 1 course.

In particular, students are expected to know:

• nomenclature, structure, and classification of organic compounds;
• structure and reactivity of the main organic functional groups;
• structural-, regio-, and stereo-isomerism;
• structure and reactivity of the most important reactive intermediates;
• fundamental organic reactions mechanisms (e.g. electrophilic and nucleophilic substitution [both aliphatic and aromatic], additions, eliminations, nucleophilic addition and acyl substitution to carbonyl groups).
• how to work properly and safely in a laboratory of organic chemistry, paying particular attention to safety rules, usage of the most common apparatuses, and standard procedures of preparation, purification, and characterization of organic compounds.

Theory:

1. Organic reactions and curly arrows.
2. Advanced stereochemistry
3. Protecting groups. Oxidations and reduction reactions.
4. Additions to conjugated systems. Nucleophilic aromatic substitution.
5. Enolates and their selective transformations.
6. Preparation and reactions of organometallic compounds
7. Organic compounds of sulfur and phosphorus and silicon
8. The Diels-Alder reaction
   
9. Radicals in organic synthesis

Laboratory:

The program of the course starts from the knowledge acquired in the course of Laboratory of Organic Chemistry I. It is formed by two parts. The first one concerns fundamental informations and principles of NMR spectroscopy and mass spectrometry to allow students to identify the products which will be prepared in ths econd part of the course. The second part of course concerns the practical preparations of several products, in parallel to subjects discussed in the course of Organic Chemistry II. NMR and GC_MS data of the compounds will be furnished at the end of each practical experiment.

Readings/Bibliography

Lectures' handouts will be made available on-line in advance

Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic chemistry 2nd Ed. Oxford, Oxford University Press, 2012.

M. D'Ischia, La Chimica Organica in Laboratorio, Casa Editrice Piccin.

R.M. Silverstein et altri, Identificazione Spettrometrica di Composti Organici, Casa Editrice Ambrosiana.

Teaching methods

Theory:

frontal lessons delivered in the classroom with the aid of the blackboard and suitable projection of slides. Classroomsolution of problemsand answers to exercises relevant to the main topics of the course. On-line exercises with the aid of the online institutional pedagogical platform [https://virtuale.unibo.it/?lang=en] .

Laboratory:

As concerns the teaching methods of this course unit, all students must attend Modules 1 and 2 [https://www.unibo.it/en/services-and-opportunities/health-and-assistance/health-and-safety/online-course-on-health-and-safety-in-study-and-internship-areas] online, while Module 3 on health and safety is to be attended in class. Information about Module 3 attendance schedule is available on the website of your degree programme

The participation to a number of practical lab activities and to the related introductory lessons is mandatory (you will have to sign an attendance sheet). Only one absence is allowed to the practical experience and to the relative explanation. Students failing to meet this requirement will not be admitted to any final written test.

Detailed synthesis procedures will be furnished to each student, together with NMR spectra of starting materials and final products

In the laboratory, there are working places with suitable equipment to perform the considered reactions.

The results of each laboratory experience must be accurately reported by each student in their laboratory notebook together with the NMR and GCMS spectra. This notebook can be drawn up on the basis of sheets provided by the teachers or independently by the student. Each student can ask instructors to correct what is reported in their laboratory notebook so that it does not contain inaccuracies or incorrect information.

The aim of the writing of this notebook is a self-assessment by the student of the degree of understanding of the experimental activities and the ability to describe them in a scientific and reproducible way.

Assessment methods

Learning assessment is achieved through a series of tests distributed during the semester of teaching and a final exam, which is held during one of the six exam calls defined by the teachers in the academic year during exam sessions.

Admission to each test is possible only through the AlmaEsami booking system. Students failing to book a test, will not be admitted. Problems must be reported before the end of the booking period.

The sum of the scores obtained in the each test constitutes the final score, which is comprised between 0 and 100. This score is first rounded to the nearest integer and then it is converted into the final grade according to the following conversion table:

score/grade conversion table

Points   Grade (/30)
0-49     fail
50-54   18
55-59   19
60-62   20
63-64   21
65-67   22
68-71   23
72-74   24
75-77   25
78-81   26
82-84   27
85-87   28
88-89   29
90-94   30
95-100 30 L

Learning of the laboratory part is assessed through six written tests:

1. written NMR/mass exercise
   How: written exercise in which the student must interpret simple spectroscopic data of NMR and mass and be able to assign them to a compound to be selected from a set of eight. The test is carried out approximately in the middle of the semester and before the practical laboratory experiences. The allotted time for this test is 60 min.
   Purpose: Purpose of the test is to assess the student's understanding of the NMR / mass concepts and the ability to apply them to the understanding and solving of simple structural recognition problems. In addition, the test also aims to prepare the student to similar problems of interpretation of NMR and mass spectra that the student will meet during the subsequent laboratory practices.
   Score: The score of this test is between 0 and 14 points Participation: The participation to this test is compulsory; in case of absence, a recovery test with the same features will be planned in the period following the end of the practical experiences in the laboratory. In case of additional absence, the student cannot participate to the final exam. The recovery test is also open to those students who wish to retry the test. In this case, the simple participation to the recovery test is considered as a definitive cancellation of the score obtained in the first NMR/MS test.
2. Final lab written test
   How: In this test students are required to answer to some practical questions about the lab experiences. The duration of the test is 90 minutes
   Purpose: The purpose of this test is to assess the degree of understanding of theoretical and experimental activities performed in the lab.
   When: This test is carried out at the end of the lab session.
   Participation: Only students thta have participated to mandatory lab practical avctivities are admitted to this test. The participation to this test is compulsory. In case of absence a recovery test with the same features will be planned, concurrently with the recovery of the NMR/MS test (see point 1.). In case of further absence, the student is not admitted to the final exam. The recovery test is also open to those students who wish to retry the test. In this case, the simple participation to the recovery test is considered as a definitive cancellation of the score obtained in the first test
   Score: The score of each form is between 0 and 16 points.
   
   Learning of the theory part is assessed through both written and oral tests:
3. Midterm
   How: written test on the topics of the first half of the course theory part. The duration of the test is 45 minutes.
   When: shortly after the middle of the semester.
   Purpose: to evaluate the degree of understanding of the concepts presented during lessons and the ability to apply them to the solution of organic chemistry problems. The test is also a self-assessment opportunity for the students, allowing them to evaluate in advance if their level of study is suitable for passing the examination and, if necessary, to make corrections to their study method in time.
   Score: This test is awarded a score of 0 to 20 points.
   Participation: optional. Students missing this test are admitted anyway to the final exam which, in this case, must be taken in full (both written and oral tests, points 4. and 5. below).
4. final theory written test
   How: written test on the topics of the entire theory program. The duration of this test is 120 minutes.
   Purpose: to assess the degree of understanding of the course topics and the ability to apply them to the solution of advanced organic chemistry problems.
   Participation: The test is compulsory and can be taken in any of the six calls that take place during exam sessions. Only students who participated to the compulsory lab tests (points 1. and 2. above).
   Score: The score of this test is between 0 and 50 points. The test is valid only if a score equal to or greater than 25 points is achieved.
5. Final theory oral test
   How: Oral examination on the topics of the entire theory program.
   Purpose: The oral test assesses the students' communication skills and their command of language in the reactional and mechanistic explanation of the steps involved in the transformation of organic molecules of medium complexity.
   Participation: The oral exam is reserved to students who did not participate to the midterm test (point 3.). It is also open to student that despite sitting the midterm test, wish to cancel the score obtained. In this case, showing up at the oral exam is considered as a definitive cancellation of the score obtained in the midterm. To be admitted to this test, students must have obtained a minimum score of 25 points in the final exam written test of the same call (point 4).
   Score: The score of this test is between 0 and 20 points.

Teaching tools

Theory: Classroom lectures with the aid of the blackboard and slide projection. Handouts and other material available through the online pedagogical platform [https://virtuale.unibo.it/?lang=en] .

Laboratory: Classroom lectures with the aid of the blackboard and slide projection. Handouts and other material available through the online pedagogical platform [https://virtuale.unibo.it/?lang=en] .

Students with learning disorders and\or temporary or permanent disabilities: please, contact the office responsible (https://site.unibo.it/studenti-con-disabilita-e-dsa/en/for-students ) as soon as possible so that they can propose acceptable adjustments. The request for adaptation must be submitted in advance (15 days before the exam date) to the lecturer, who will assess the appropriateness of the adjustments, taking into account the teaching objectives.

Office hours

See the website of Paolo Righi

See the website of Andrea Mazzanti

See the website of Mariafrancesca Fochi