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

Prerequisites

In general, students are expected to have achieved all the learning outcomes of the Organic Chemistry I course.

In particular, students should be familiar with:

• the nomenclature and structure of organic compounds, and the correct representation of organic molecular structures;

• the structure and reactivity of the various functional groups found in organic molecules;

• the concepts of structural isomerism, regioisomerism, and stereoisomerism;

• the structure and reactivity of reactive intermediates;

• the fundamental reactions of organic compounds, including electrophilic and nucleophilic substitutions (both aliphatic and aromatic), additions, eliminations, nucleophilic additions and acyl substitutions of carbonyl compounds, and the chemistry of amines;

• the basic principles of the main experimental operations in Organic Chemistry, and the selection of purification techniques such as distillation, solvent extraction, crystallization, and chromatography;

• the risks associated with laboratory work and the safe handling of reagents and basic laboratory equipment.

Theory Course Contents

• Organic reactions and the use of curved-arrow notation

• Advanced stereochemistry

• Oxidations, reductions, and protecting groups

• Additions to conjugated systems; nucleophilic aromatic substitution

• Formation and reactions of enolates

• Formation and reactions of organometallic compounds

• Organic compounds of sulfur, phosphorus, and silicon

• The Diels–Alder reaction

• Radical reactions

Laboratory Course Contents

The laboratory component of the course, which continues the activities introduced in the Organic Chemistry I Laboratory, consists of two parts.

In the first part, delivered at the beginning of the course, students will be introduced to the general principles of NMR spectroscopy and mass spectrometry, including specific practical sessions in the computer laboratory. These activities are designed to enable students to identify and characterize the products they will synthesize during the second part of the course.

In the second part, students will prepare several compounds using synthetic methodologies that are closely related to the topics covered in Organic Chemistry II. Students will be provided with the GC–MS and NMR analyses of the compounds they have synthesized.

Readings/Bibliography

Course materials made available by the instructors through the Virtuale online learning platform.

• Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford: Oxford University Press, 2012. [link]

• R. M. Silverstein, F. X. Webster, D. J. Kiemle, D. L. Bryce Spectrometric Identification of Organic Compounds, 8th Ed., Wiley 2014 [link]

Teaching methods

Theory

Lectures are delivered through traditional classroom teaching, using both the blackboard and slide presentations. Summary and problem-solving sessions are conducted in class to review and consolidate the topics covered. Additional exercises and learning activities are provided through the Virtuale online learning platform.

 

Laboratory

Given the nature of the activities and teaching methods adopted, participation in this educational activity requires all students to complete Modules 1 and 2 through e-learning and to attend Module 3, which provides specific training on health and safety in study and laboratory environments. Information regarding schedules and attendance procedures for the various modules is available in the dedicated section of the degree programme website.

Attendance is mandatory for:

• the computer laboratory sessions on NMR Spectroscopy;

• the practical activities carried out in the chemistry teaching laboratories;

• the classroom presentations and discussions related to the laboratory activities.

Compliance with the attendance requirement will be verified through the collection of signatures for each examination, practical session, exercise, or lecture designated as mandatory.

Only one absence is permitted from activities requiring mandatory attendance. Students who accumulate two or more absences from practical laboratory activities will not have fulfilled the attendance requirement and will be required to repeat the mandatory laboratory activities in a subsequent academic year (see Assessment and Evaluation Methods, sections 2 and 4).

The computer laboratory activities (Module 2 of the course) will be carried out using dedicated software for the processing and interpretation of NMR spectra (MestReNova). Students will be provided with a set of raw NMR data on which they will perform spectral processing and data interpretation exercises. The software used in the computer laboratory is available to all students.

For the activities carried out in the chemistry teaching laboratory (Module 3 of the course), students will be provided with the experimental procedures required for the syntheses, together with the NMR spectra of both starting materials and reaction products. Experimental work will take place in the UE5 teaching laboratories. Each workstation will be equipped with the electrical equipment and glassware necessary to perform the assigned syntheses. Every laboratory experiment will be preceded by a compulsory introductory session explaining the technical aspects and safety considerations associated with the experimental activity.

The results of each chemistry laboratory experiment must be accurately recorded by every student in their laboratory notebook during the course of the experiment, together with the corresponding NMR and GC–MS spectra. The notebook may be prepared using templates provided by the instructors or independently, in a format chosen by the student. Students may ask the laboratory instructors to review the contents of their notebooks to ensure that they do not contain inaccuracies or incorrect information.

The purpose of maintaining the laboratory notebook is to encourage students to assess their own understanding of the experimental activities performed and to develop their ability to describe them in a scientific, accurate, and reproducible manner.

Assessment methods

Student learning is assessed through a series of evaluations conducted throughout the academic year, and a final examination taken during one of the six examination sessions scheduled by the instructors within the examination periods established by the Degree Programme.

Registration for all examinations is mandatory and must be completed through the AlmaEsami system. Students who are not registered will not be admitted to the examinations. Any issues related to access to the registration system must be reported in advance and, in any case, before registration closes.

Each assessment is assigned a score. The sum of the scores obtained in the various assessments ranges from 0 to 100 points and constitutes the final score. This score is first rounded to the nearest whole number and then converted into the final mark out of 30 according to the following conversion table.

Conversion of Total Score into Final Grade
Points     Grade (/30)
0-49       not passed
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 cum laude 

To pass the course and obtain a final grade, students must complete two laboratory assessments and two theory assessments, as described below.

 

The use of artificial intelligence (AI) tools is not permitted in any assessment activity associated with this course. Any use of such tools will be considered a breach of academic integrity and will be handled in accordance with University regulations.

 

Assessment of Laboratory Learning

Laboratory learning is assessed through two written examinations.

1. NMR/Mass Spectrometry Written Test
   Format: A written exercise in which students must interpret simple NMR and mass spectrometric data and assign them to the correct compound selected from a set of eight possible structures. The examination lasts 60 minutes.
   When: Approximately midway through the semester, before the practical laboratory sessions begin.
   Purpose: The aim of this assessment is to evaluate students’ understanding of the NMR and mass spectrometry concepts presented during the course and their ability to apply these concepts to the solution of simple structural identification problems. The test also serves as preparation for the interpretation of NMR and mass spectra encountered during the subsequent laboratory activities.
   Score: A score between 0 and 14 points is awarded.
   Participation: Attendance is mandatory. Students who are absent may take a make-up test, administered under the same conditions on the same day of the first summer examination session. Students who are absent from the make-up test must retake this assessment in a subsequent academic year. 
   Students who took the original test but wish to discard their score may also sit the make-up test. Mere attendance at the make-up test constitutes an irrevocable waiver of the score obtained in the original NMR/Mass Spectrometry test.
2. Laboratory Written Test
   Format:This written examination consists of practical questions related to the laboratory experiments performed during the course. The examination lasts 60 minutes.
   Purpose: The aim of the assessment is to verify students’ understanding of both the theoretical principles and the practical aspects of the laboratory activities.
   When: Shortly after completion of the laboratory sessions.
   Score: A score between 0 and 16 points is awarded.
   Participation: Only students who have fulfilled the laboratory attendance requirement are eligible to take this examination.
   Attendance at this assessment is mandatory. Students who are absent may take a make-up examination, administered under the same conditions and at the same time as the NMR/Mass Spectrometry make-up test (see Section 1). Students who are absent also from the make-up examination must retake this assessment in a subsequent academic year.
   Students who took the original laboratory written test but wish to discard their score may also sit the make-up examination. Mere attendance at the make-up examination constitutes an irrevocable waiver of the score obtained in the original laboratory written test.
   
   Assessment of Theory Learning
   Theory learning is assessed through both written and oral examinations.
   
   
3. Midterm Examination
   Format: A written examination covering the topics presented during the first part of the theory course. The examination lasts 45 minutes.
   When: Approximately midway through the semester.
   Purpose: The purpose of the assessment is to evaluate students’ understanding of the concepts presented during lectures and their ability to apply these concepts to the solution of organic chemistry problems. The examination provides an opportunity for self-assessment, enabling students to evaluate whether their level of preparation is sufficient for success in the course and, if necessary, to adjust their study methods in a timely manner.
   Score: A score between 0 and 20 points is awarded.
   Participation: The examination is optional. Students who do not take the midterm examination may still sit the final examination, which must then be completed in its full written-and-oral format (see Sections 4 and 5).
4. Final Written Theory Examination
   Format: A written examination covering the entire theory syllabus. The examination is mandatory and lasts 120 minutes.
   When: It may be taken during any examination session scheduled after the end of the semester.
   Purpose: The aim of the examination is to assess students’ understanding of the concepts presented during the course and their ability to apply them to the solution of advanced organic chemistry problems.
   Score: A score between 0 and 50 points is awarded. The examination is considered passed only if the student obtains at least 25 points.
   Participation: Mandatory; no admission requirements apply.
5. Final Oral Theory Examination
   Format: An oral examination covering the entire theory syllabus.
   Purpose: The oral examination assesses students’ communication skills, scientific competence, and mastery of appropriate chemical terminology in explaining the reaction pathways and mechanisms involved in the transformation of moderately complex organic molecules.
   Score: A score between 0 and 20 points is awarded.
   Participation: This examination is mandatory for students who did not take the midterm examination (Section 3) or who wish to waive the score obtained in that examination. Mere attendance at the oral examination constitutes an irrevocable waiver of any score previously obtained in the midterm examination.
   To be admitted to the oral examination, students must have passed the final written theory examination in the same examination day (Section 4).

 

Validity of Scores:
The score obtained in each individual assessment remains valid until the student chooses to retake that assessment. Mere attendance at a subsequent sitting of the same assessment constitutes an irrevocable waiver of the score previously obtained in that assessment. Scores obtained in all other assessments remain valid.

Teaching tools

Theory: Lectures are delivered through traditional classroom teaching, using both the blackboard and slide presentations. Teaching materials are made available online through the Virtuale learning platform. Summary and review sessions are conducted in class to reinforce and consolidate the topics covered during the course.

Laboratory: Laboratory activities are supported by lectures delivered using both the blackboard and slide presentations. All materials presented during these sessions are made available online through the Virtuale learning platform.Students with Specific Learning Disorders (SLD) or Disabilities

Students with Specific Learning Disorders (SLD) or temporary or permanent disabilities are strongly encouraged to contact the relevant University office well in advance. The office will propose any appropriate accommodations to the students concerned. Such accommodations must, however, be submitted to the course instructor for approval at least 15 days in advance. The instructor will evaluate their suitability, taking into account the learning objectives of the course.

Office hours

See the website of Paolo Righi

See the website of Andrea Mazzanti

See the website of Mariafrancesca Fochi