
Synthetic Methods
Code: 102527Credits: 6
| Degree programme | Type | Course |
|---|---|---|
| Chemistry | OB | 3 |
Contact lecturer
- Name :
- Ona Illa Soler
- Email :
- ona.illa@uab.cat
Teaching staff
- Joan Pau Bayon Rueda
Group languages
You can consult this information at the end of the document.
Prerequisites
Since the content of this course is a continuation and extension of the course Structure and Reactivity of Organic Compounds (ERCO), it is strongly recommended to have passed this second-year course before enrolling in Synthetic Methods.
Objectives
To deepen the study of the reactivity of organic compounds, considering the following aspects:
1. Study of new methods for the formation of carbon–carbon and carbon–heteroatom bonds and for the interconversion of functional groups.
2. Study of reaction mechanisms: kinetic and non-kinetic tools, and theoretical models.
3. Study of the influence of reaction conditions on selectivity and yield.
4. Study of methodological tools for the design of the synthesis of new organic compounds from simple and commercially available precursors.
Learning outcomes
- Communicate orally and in writing in one's own language.
- Manage the organisation and planning of tasks.
- Resolve problems and make decisions.
- Obtain information, including by digital means.
- Manage, analyse and synthesise information.
- Use IT to treat and present information.
- Have numerical calculation skills.
- Work in a team and show concern for interpersonal relations at work.
- Reason in a critical manner
- Be ethically committed.
- Learn autonomously.
- Adapt to new situations.
- Propose creative ideas and solutions.
- Show initiative and an enterprising spirit.
- Show motivation for quality.
- Show sensitivity for environmental issues.
- Describe the different types of isomerism in organic compounds.
- Identify the basic reactivity associated with the various functional organic groups.
- Identify the functional groups of the principal natural organic products and their most important reactions.
- Describe the most relevant synthetic methodologies for the inter-conversion of functional groups and the formation of simple and multiple carbon-carbon bonds.
- Describe the mechanisms of the principal organic reactions and the various factors that affect them.
- Determine and represent the configuration of chiral centres in organic compounds.
- Identify the isometric relationship between different structures of organic compounds.
- Predict the reactivity of different organic functional groups under certain reaction conditions, as well as the structure of the products obtained.
- Propose simple synthetic methods to obtain certain organic compounds from certain reagents.
- Propose reaction mechanisms in processes involving organic compounds.
Contents
Topic 1. Formation of C–C bonds from compounds with an activated methylene group
Formation of enolates. Regioselectivity. Kinetic and thermodynamic control. Factors affecting this process (type of base, counterion, solvent). Selectivity between C- and O-alkylation. Formation of lithium enolates, silyl enol ethers, enamides, and azaenolates; application in alkylation reactions. Alkylation of aldehydes using dithianes. Directed aldol additions. Knoevenagel reaction. Mannich reaction. Conjugate additions. Robinson annulation. Directed acylations.
Topic 2. Formation of C–C bonds involving organometallic reagents
General concepts of organolithium and organomagnesium compounds. Felkin-Anh model. Organocuprates. Reformatsky reaction. Palladium-promoted reactions.
Topic 3. Formation of C–C bonds via concerted reactions
Frontier molecular orbitals. Woodward–Hoffmann selection rules. Electrocyclic reactions. Thermal and photochemical [2+2] cycloadditions. Diels–Alder reaction: regio- and stereoselectivity. [3,3]-sigmatropic rearrangements: Cope and Claisen rearrangements.
Topic 4. Formation of C=C bonds
Thermal β-eliminations: Hofmann and Cope elimination, selenoxide elimination. Wittig reaction: types of ylides, preparation, reactivity, and stereoselectivity. Horner–Wadsworth–Emmons reaction. Sulfur ylides: types, preparation, and reactivity. Alkene metathesis reaction.
Topic 5. Reactions involving highly reactive electron-deficient intermediates
Radical intermediates: addition of thiols to alkenes. Cationic intermediates: Wagner–Meerwein rearrangements and cyclizations. Carbenes: preparation and reactivity, cyclopropanation, Simmons–Smith reaction, Wolff rearrangement, Arndt–Eistert homologation. Nitrenes: preparation and reactivity, Curtius, Schmidt, Hofmann, and Beckmann rearrangements.
Topic 6. Reduction reactions
Hydrogenation: heterogeneous and homogeneous catalysis. Hydrogenolysis. Use of boron and aluminum hydrides: selectivity. Reductive amination. Reduction with alkali metals in solution: Birch and Bouveault–Blanc reactions, dehalogenation. Deoxygenation: Clemmensen and Wolff–Kishner reactions. Desulfurization of dithianes.
Topic 7. Oxidation reactions
Oxidation of alcohols: Cr(VI) reagents, MnO₂, Swern oxidation, Dess–Martin oxidation. Oxidation of alkenes: KMnO₄, OsO₄, peroxides and peracids, Sharpless asymmetric epoxidation, oxidative cleavage. Oxidation of aldehydes and ketones: to carboxylic acids and Baeyer–Villiger reaction.
Topic 8. Methods for determining reaction mechanisms. Effect of molecular structure on reactivity
Kinetic and thermodynamic data. Curtin–Hammett principle. Kinetic isotope effect. Introduction to Hammett correlations. Non-kinetic methods: isotopic labeling; crossover experiments; stereochemical data; detection/trapping of intermediates.
Learning activities and methodology
| Title | Hours | ECTS | Learning outcomes |
|---|---|---|---|
| Studing, problem solving | 82 | 3.28 | |
| Preparing exercises to hand in | 5 | 0.2 | 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 |
| Master classes | 37 | 1.48 | 1, 2, 4, 5, 6, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 |
| Problem and exersice classes | 12 | 0.48 | 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 |
The Virtual Campus will be used to provide students with all the material considered necessary by the teaching staff for the learning process: course syllabus, lecture presentations, problem sets, etc. Throughout the course, students must participate in different learning activities in order to acquire the established knowledge and skills. Four types of activities will be carried out:
1. In-person theory classes
During part of the in-person sessions, the teaching staff will highlight the basic theoretical aspects of the different topics, which must be studied individually by consulting the material available on the virtual campus and the corresponding bibliography. Time will also be devoted to resolving students’ doubts and discussing the most relevant aspects of each topic.
2. In-person problem-solving classes
Throughout the course, students will be given problem sheets to solve. In the in-person problem sessions, the solutions proposed by the students based on their independent work will be discussed. Special emphasis will be placed on active student participation.
3. Submission of exercises (individual work)
During the course, the teaching staff will assign different exercises that students must solve individually either during in-person sessions or submit electronically by the indicated deadline.
Assessment
Continuous assessment activities
| Title | Weight | Hours | ECTS | Learning outcomes |
|---|---|---|---|---|
| Exercise handing in | 15% | 4 | 0.16 | 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 |
| Partial and second-chance exams | 85% | 10 | 0.4 | 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 |
Assessment in this course will be continuous, in order to encourage sustained student effort and thereby facilitate learning. This methodology also provides the teaching staff with information on how well students assimilate the content and their ability to apply it in problem-solving. Assessment will be individual.
Submission of exercises:
Throughout the course, when deemed appropriate by the teaching staff, students must solve some exercises during class time or submit them within previously established deadlines. The exercises may include material from Organic Chemistry courses taken in previous years. This component will account for 15% of the overall continuous assessment grade.
Exams:
Two midterm exams will be held during the course to assess students’ knowledge of the theoretical content as well as their ability to solve problems.
First midterm exam
This exam will assess approximately 50% of the course content. It may include both theoretical and practical questions (problem-solving) and will account for 40% of the overall continuous assessment grade. There is no minimum grade required on this exam to average it with the second midterm exam.
Second midterm exam
This exam will assess the full course content, with particular emphasis on material covered after the first midterm. It may include both theoretical and practical questions (problem-solving) and will account for 45% of the overall continuous assessment grade. A minimum grade of 4 out of 10 is required in this exam in order to average it with the other grades.
To pass the course initially, a minimum of 5 out of 10 must be obtained after calculating the weighted average of all continuous assessment components (2 exams and exercise submissions).
Resit exam
Students who do not pass the course through continuous assessment will have the option to take a resit exam. To pass, the resit exam grade must be higher than 5 out of 10, and the final course grade will be the weighted average of the exam (85%) and the exercise submissions (15%).
To be eligible for the resit exam, students must have taken at least one of the two midterm exams.
If a student has only been assessed on at most 33% of the evaluation components and withdraws, the final grade will be “NOT ASSESSED.”
Single assessment: Students who have opted for single assessment must take a final exam covering the entire course content on the same day as the second midterm of the continuous assessment group. Their grade will be the result of this exam, which must be at least 5 out of 10 to pass the course. If the final grade is below 5, the student has another opportunity to pass the course through the resit exam, which will be held on the same day as the resit exam for continuous assessment students. The grade will be that of this exam, which must be equal to or higher than 5 out of 10 to pass.
Use of AI
Permitted use: “In this course, the use of Artificial Intelligence (AI) technologies is allowed as an integral part of the development of coursework, provided that the final result reflects a significant contribution from the student in terms of analysis and personal reflection. The student must clearly identify which parts have been generated using this technology, specify the tools used, and include a critical reflection on how they have influenced the process and the final outcome of the activity. Lack of transparency in the use of AI will be considered a breach of academic integrity and may result in a penalty in the activity grade, or more severe sanctions in serious cases.”
Academic fraud
The commission of any irregularity in an assessment activity (academic fraud, plagiarism, or improper use of AI, unless such use is expressly authorized in the course guide) that may lead to a significant change in the grade will result in that activity being graded as 0. If the course guide establishes that passing the subject requires obtaining a minimum grade in this assessment activity, or if multiple irregularities occur in the assessment activities of the same subject, the final grade for the subject will be 0. Additionally, disciplinary proceedings may be initiated against any student who commits any of these irregularities.
Bibliography
Textbooks:
Clayden, J., Greeves, N., & Warren, S. G. (2012). Organic chemistry (2nd ed.). Oxford University Press.(ISBN: 978-0-19-9270293).
https://bibcercador.uab.cat/permalink/34CSUC_UAB/1fbc57r/alma991004061659706709
Carey, F. A., & Sundberg, R. J. (2007). Advanced Organic Chemistry : Part A: Structure and Mechanisms (5th ed. 2007.). Springer US. https://doi.org/10.1007/978-0-387-44899-2
(e-ISBN-13: 978-0-387-44899-2)
https://bibcercador.uab.cat/permalink/34CSUC_UAB/1fbc57r/alma991010407378506709
Smith, M. B., & March, J. (2020). March’s Advanced Organic Chemistry - Reactions, Mechanisms, and Structure (8th Edition) (Eighth edition). John Wiley & Sons. (ISBN:978-1-119-37178-6)
https://bibcercador.uab.cat/permalink/34CSUC_UAB/rokuu2/cdi_knovel_primary_book_kpMAOCRM13
Web links:
IUPAC Dictionary of Chemical Terminology: http://goldbook.iupac.org/
Nomenclature and Structure Drawing:
Free Chemical Drawing Software for Students | ChemSketch | ACD/Labs
Marvin - Chemical Drawing Software
Organic Chemistry Portal: www.organic-chemistry.org
Software
There isn't any.
Course groups and languages
The information provided is provisional until November 30. After this date, you will be able to consult the language of each group through this link. To access the information, you will need to enter the course CODE
| Type of teaching | Group | Language | Semester | Shift |
|---|---|---|---|---|
| (TE) Theory | 1 | Catalan | first semester | morning-mixed |
| (PAUL) Classroom practices | 1 | Catalan/Spanish | first semester | morning-mixed |
| (TE) Theory | 2 | Catalan | first semester | afternoon |
| (PAUL) Classroom practices | 2 | Catalan/Spanish | first semester | afternoon |