66687 - Organic Chemistry II and Laboratory

Course Unit Page

SDGs

This teaching activity contributes to the achievement of the Sustainable Development Goals of the UN 2030 Agenda.

Good health and well-being Quality education Industry, innovation and infrastructure Responsible consumption and production

Academic Year 2021/2022

Learning outcomes

At the end of the course the student understands the basic reactivity of polyfunctional carbonyl compounds, of aromatic heterocyclic compounds as well as of organic free radicals. The student is able to predict the chemical behaviour of the pericyclic reactions following the symmetry rules of the interacting molecular orbitals; to choose appropriate methodologies for the use of protecting groups; to know oxidation and reduction reactions of organic molecules; various synthetic methods using organometallic compounds; the typical reactions of organic compounds bearing sulfur and phosphorus; the basic chemistry of carbohydrates. The student is able to discuss synthetic pathways, to analyze appropriate synthetic methods as well as to perform the synthesis of organic molecules of average complexity through the use of usual procedures. The student is additionally able to follow the progress of every organic reaction as well as to characterize the outcoming products by means of common analytical techniques including Nuclear Magnetic Resonance (NMR), Mass Spectroscopy (MS) and Gas Chromatography (GLC).

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. Protecting groups. Oxidations and reduction reactions.
  3. Additions to conjugated systems. Nucleophilic aromatic substitution.
  4. Formation and reaction of enolates.
  5. Reaction of enolates with carbonyl compounds.
  6. Organic compounds of lithium, magnesium, copper, zinc and boron.
  7. Organic compounds of sulfur, phosphorus and silicon.
  8. Heteroaromatic compounds
  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.

 

Laboratory:

As concerns the teaching methods of this course unit, all students must attend Modules 1 and 2 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 of students to a number of lab experiences and to related introductory lessons is mandatory (Students' will have to sign an atendance 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 the final exam.

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. Written lab 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
    : 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 60 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. This score has a 12-month validity after which it must be repeated or the oral part of the final exam must be taken (see point 5. below)
    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 exam - 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) are admitted to this test.
    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 exam - oral exam
    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 compulsory only for 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.

Laboratory: Classroom lectures with the aid of the blackboard and slide projection. Handouts and other material available through the online pedagogical platform.

Students with specific learning disabilities (SLD) or other disabilities, can contact the University Service for Students with Disabilities (http://www.studentidisabili.unibo.it/) or the contact person of the Department (giorgio.bencivenni2@unibo.it) or the teachers of the course.

Office hours

See the website of Paolo Righi

See the website of Mariafrancesca Fochi

See the website of Luca Bernardi

See the website of Michele Mancinelli