Organic Chemistry II and Laboratory 1
Module MODULO 2

Academic Year 2026/2027 - Teacher: NUNZIO CARDULLO

Course Structure

The course consists of 6 CFU, divided between hours of theoretical lectures and hours of laboratory practice. The theoretical lecture hours are a prerequisite for carrying out the laboratory practice.

If  the course would be delivered in blended or telematic learning mode, the necessary changes may be introduced with respect to what has been previously stated, in order to comply with the program set out in the syllabus.

Required Prerequisites

Basic Concepts of General Chemistry and Organic Chemistry I

Attendance of Lessons

Attendance is mandatory, with the exceptions established by the degree program's teaching regulations. Students must attend at least 70% of the scheduled hours in order to be admitted to the exam. If this minimum number of hours is not reached, the student will be required to pass a practical test before taking the regular exam.

Detailed Course Content

  1. Introductory concepts on common identification techniques such as: 1H NMR and 13C NMR, IR, UV-Vis.
  2. Theoretical concepts on the correct use of laboratory equipment for safely carrying out chemical reactions.
  3. Theoretical description and theoretical execution of the following reactions and of the processes required for the isolation and purification of the products:

  • Electrophilic aromatic substitution: synthesis of p-nitroaniline (protecting groups).
  • Multistep synthesis: preparation of a local anesthetic (benzocaine), nucleophilic acyl substitution.
  • Synthesis of dibenzalacetone: aldol condensation reaction.
  • Synthesis of methyl salicylate and purification by distillation.

        4. Characterization of the products obtained in each experiment by means of melting point, UV-Vis, IR, 1H and 13C NMR.

Information for students with disabilities and/or specific learning disorders (SLD)

To ensure equal opportunities and in compliance with current legislation, interested students may request a personal meeting in order to plan any compensatory and/or dispensatory measures, based on the teaching objectives and specific needs.

Textbook Information

  1. D.L. Pavia, G.M. Lampman, G.S. Kritz, Introduction to Organic Laboratory, Saunder College Pubblishing.
  2. R.M. Silverstein, F.X. Webster, Identificazione Spettroscopica di Composti Organici, Ambrosiana.
  3. L.M. Harwood, C.J. Moody “Experimental organic chemistry” Ed. Wiley-Blackwell.
  4. The teaching material prepared by the instructor (slides, handouts), in addition to the recommended textbooks, will be available through the STUDIUM platform.

Course Planning

 SubjectsText References
1UV-Vis; IR; 1H- e 13C-NMR spectroscopy: Theoretical aspects and practical applicationsR.M. Silverstein, F.X. Webster, Spectrometric identification of Organic Compounds
2D.L. Pavia, G.M. Lampman, G.S. Kritz,  Introduction to Organic Laboratory, Saunder College Pubblishing.Teaching material prepared by the professor
3Teaching material prepared by the professor
4D.L. Pavia, G.M. Lampman, G.S. Kritz,  Introduction to Organic Laboratory, Saunder College Pubblishing. Teaching material prepared by the professor
5R.M. Silverstein, F.X. Webster, Spectrometric identification of Organic Compounds. Teaching material prepared by the professor

Learning Assessment

Learning Assessment Procedures

The exam, integrated with Module 1, is aimed at assessing the acquisition of the basic concepts of the course and the ability to connect them with one another and with the experiments carried out in the laboratory, the ability to clearly present concepts using appropriate scientific language, and the ability to quantitatively use and interpret experimental data by applying the concepts and methodologies acquired during the course.

The oral exam will cover both the discussion of a laboratory experience and topics from the theoretical course.

For each laboratory experience, the student must submit a detailed report within 7 days of the exam date; this report will also be subject to evaluation as part of the exam. The final grade will be assigned based on the following criteria:

Grade 29–30 cum laude: The student has an in-depth knowledge of the synthesis strategies used in the laboratory and of the spectroscopic techniques that can be used for structural characterization; is able to integrate and critically analyze the questions presented, and to autonomously extend the topics studied to other cases; demonstrates excellent communication skills and command of language.

Grade 26–28: The student has a good knowledge of the synthesis strategies used in the laboratory and of the spectroscopic techniques that can be used for structural characterization; is able to describe a process, and to integrate and analyze the questions presented in a critical and coherent manner; presents the topics clearly, using appropriate language.

Grade 22–25: The student has a fair knowledge of the synthesis strategies used in the laboratory and of the spectroscopic techniques that can be used for structural characterization, and presents the topics in a reasonably clear manner with a fair command of language.

Grade 18–21: The student has minimal knowledge of the synthesis strategies used in the laboratory and of the spectroscopic techniques that can be used for structural characterization; has a modest ability to describe a purification process; presents the topics with sufficient clarity, although command of language is not well developed.

Failing grade: The student does not possess the minimum required knowledge of the main contents of the course. The ability to use specific terminology is very poor or absent, and the student is not able to independently apply the concepts.

Should it become necessary, for contingent reasons, to activate distance learning, the assessment of student preparation will take place in accordance with the regulatory provisions specifically issued by the University's governing bodies.

Examples of frequently asked questions and / or exercises

Column chromatographic separation

Separation and purification techniques for the desired compounds

Describe and comment on the procedure of experiment X

How can the progress of an organic reaction be monitored?

How many vibrational transitions a molecule made up of N atoms has? Are they all IR active?

What does the frequency of a particular stretching motion depend on? Which approximation is used?

What do the intensity and width of an IR signal depend on?

Which regions can be identified in an IR spectrum?

What are the characteristic bands of the OH, NH, and CH groups?

How can we distinguish ortho, meta, and para substituted aromatic rings?

What transitions does the interaction of NMR radiation with matter generate?

What does the magnetic moment of a nucleus depend on?

How many orientations can a nucleus with I=1/2 assume when placed in an external magnetic field? What does the energy difference between them depend on?

What is the Larmor frequency?

Why is TMS (or similar compounds) used as a reference?

How do protons bonded to heteroatoms behave?

What is spin-spin coupling? How is the multiplicity of a signal determined?

Comment on a proton or carbon-13 spectrum.

What are the differences between 1H and 13C NMR spectroscopy?

What type of solvents do we use for NMR analysis?

Which region of the electromagnetic spectrum does UV-vis spectroscopy use? What transitions does the interaction of UV-vis radiation with matter generate?

What are transmittance and absorbance? What does A depend on?

Which energy levels are involved in UV-vis spectra?

Which electronic transitions can be observed in the UV-vis region?

How does an increase in conjugation affect the UV-vis spectrum?

What are the characteristic bands of aromatic systems? How are they affected by substituents?

What is the difference between a chromophore group and an auxochrome?