Organic Chemistry B
A.Y. 2026/2027
Learning objectives
The objective of the course is to make students develop a base of knowledge of the most fundamental organic reactions in the realm of organic synthesis.
Expected learning outcomes
At the end of the course, the student should be able to select suitable reactions for a particular organic synthesis, based on the identification of the most effective possibilities among the available ones.
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Single session
Responsible
Lesson period
Second semester
Course syllabus
- Alkylation of enolates and other nucleophilic carbons. generation and properties of enolates and other stabilized carbanions: generation of enolates by deprotonation; regioselectivity and stereoselectivity in the formation of enolates; other methods of generating enolates; solvent effects on the structure and reactivity of enolates. Alkylation of enolates: alkylation of highly stabilized enolates; alkylation at carbon and oxygen; alkylation of ketone enolates; alkylation of aldehydes, esters, carboxylates, amides and nitriles; generation and alkylation of dianions; intramolecular alkylation reactions of enolates; control of enantioselectivity in alkylation reactions. Nitrogen analogues of enols and enolates: enamines and anions of imines. Problems.
- Reactions of carbon nucleophiles with carbonyl groups. Aldol addition and aldol condensation reactions: mechanism study; mixed aldol condensations with aromatic aldehydes; control of regio- and stereochemistry in mixed aldol reactions of aldehydes and aliphatic ketones; control of regio- and stereoselectivity in aldol reactions of aldehydes and ketones; aldol reactions of enolates of esters and other carbonyl derivatives; mukaiyama aldol reaction; control of facial selectivity in aldol and mukaiyama reactions; intramolecular aldol reactions and robinson annulation. Reactions of addition to imines and immonium ions: mannich reaction; additions to n-acyliminium ions; amine-catalyzed condensation reactions. Acylation reactions of carbanions: claisen; dieckmann; acylation of enolates and other nucleophilic carbons. Olefination reactions: wittig reaction and related reactions; reactions of carbonyl compounds with α-silyl carbanions; julia olefination reaction. Reactions proceeding via addition-cyclization: sulfur ylides and related nucleophiles; darzens reaction. Conjugate addition reactions of carbon nucleophiles: conjugate addition of enolates; conjugate addition with tandem alkylation; conjugate addition of enolate equivalents (mukaiyama-michael); control of facial selectivity in conjugate addition reactions; conjugate addition of organometallic reagents; conjugate addition of cyanide ion. Problems.
- Electrophilic additions to C-C multiple bonds. electrophilic additions to alkenes: addition of hydrogen halides, hydration, oximercuration, addition of halogens, reactions with electrophiles based on sulfur and selenium. Electrophilic cyclization reactions: halocyclization; sulfenylcyclization and selenenylcyclization; cyclization via mercury ion. Electrophilic substitution reactions at α to the carbonyl group: halogenation, sulfenylation, and selenenylation at α to carbonyl groups. Additions to allenes and alkynes. Addition to double bonds via organoboron intermediates: hydroboration; reactions of organoboranes (transformations to alcohols, amines, halides); enantioselective hydroboration, hydroboration of alkynes. Hydroalumination, carboalumination, hydrozirconation, and related reactions. Problems.
- Organometallic compounds of groups I, II, and III. Preparation, properties, and reactions of organomagnesium, organolithium, organozinc, organocadmium, organomercury, organoindium, and organocerium compounds. Problems. Carbanions and other carbon nucleophilic species (acidity of hydrocarbons; carbanions stabilized by functional groups; enols and enamines; carbanions as nucleophiles in SN2 reactions; problems).
- Exercises on the course topics and on the use of the most common databases for organic synthesis planning. Compared to previous editions, the exercises will focus on a smaller number of solved problems in order to deepen, step by step, the proposed resolution. Furthermore, interactive group exercises (using appropriate educational tools) will be introduced for the first time in this teaching course in order to facilitate, in a dynamic way, the learning of the organic syntheses proposed during the course.
- Reactions of carbon nucleophiles with carbonyl groups. Aldol addition and aldol condensation reactions: mechanism study; mixed aldol condensations with aromatic aldehydes; control of regio- and stereochemistry in mixed aldol reactions of aldehydes and aliphatic ketones; control of regio- and stereoselectivity in aldol reactions of aldehydes and ketones; aldol reactions of enolates of esters and other carbonyl derivatives; mukaiyama aldol reaction; control of facial selectivity in aldol and mukaiyama reactions; intramolecular aldol reactions and robinson annulation. Reactions of addition to imines and immonium ions: mannich reaction; additions to n-acyliminium ions; amine-catalyzed condensation reactions. Acylation reactions of carbanions: claisen; dieckmann; acylation of enolates and other nucleophilic carbons. Olefination reactions: wittig reaction and related reactions; reactions of carbonyl compounds with α-silyl carbanions; julia olefination reaction. Reactions proceeding via addition-cyclization: sulfur ylides and related nucleophiles; darzens reaction. Conjugate addition reactions of carbon nucleophiles: conjugate addition of enolates; conjugate addition with tandem alkylation; conjugate addition of enolate equivalents (mukaiyama-michael); control of facial selectivity in conjugate addition reactions; conjugate addition of organometallic reagents; conjugate addition of cyanide ion. Problems.
- Electrophilic additions to C-C multiple bonds. electrophilic additions to alkenes: addition of hydrogen halides, hydration, oximercuration, addition of halogens, reactions with electrophiles based on sulfur and selenium. Electrophilic cyclization reactions: halocyclization; sulfenylcyclization and selenenylcyclization; cyclization via mercury ion. Electrophilic substitution reactions at α to the carbonyl group: halogenation, sulfenylation, and selenenylation at α to carbonyl groups. Additions to allenes and alkynes. Addition to double bonds via organoboron intermediates: hydroboration; reactions of organoboranes (transformations to alcohols, amines, halides); enantioselective hydroboration, hydroboration of alkynes. Hydroalumination, carboalumination, hydrozirconation, and related reactions. Problems.
- Organometallic compounds of groups I, II, and III. Preparation, properties, and reactions of organomagnesium, organolithium, organozinc, organocadmium, organomercury, organoindium, and organocerium compounds. Problems. Carbanions and other carbon nucleophilic species (acidity of hydrocarbons; carbanions stabilized by functional groups; enols and enamines; carbanions as nucleophiles in SN2 reactions; problems).
- Exercises on the course topics and on the use of the most common databases for organic synthesis planning. Compared to previous editions, the exercises will focus on a smaller number of solved problems in order to deepen, step by step, the proposed resolution. Furthermore, interactive group exercises (using appropriate educational tools) will be introduced for the first time in this teaching course in order to facilitate, in a dynamic way, the learning of the organic syntheses proposed during the course.
Prerequisites for admission
Content that constitutes an essential prerequisite for successfully following the course: elements of classical organic synthesis (synthesis and modification of organic functional groups, formation of carbon-nitrogen, carbon-oxygen, and carbon-carbon bonds).
These topics are typically covered in basic organic chemistry courses (Organic Chemistry 1 and Organic Chemistry 2) in the Bachelor's degree programs in Chemistry and Industrial Chemistry.
These topics are typically covered in basic organic chemistry courses (Organic Chemistry 1 and Organic Chemistry 2) in the Bachelor's degree programs in Chemistry and Industrial Chemistry.
Teaching methods
Traditional frontal lectures. Blackboard exercises or using interactive educational tools (Wooclap).
Teaching Resources
- F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reactions and Synthesis, V Edition, 2007 Springer Science.
- F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, V Edition, 2007 Springer Science.
- F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, V Edition, 2007 Springer Science.
Assessment methods and Criteria
Written tests (3 "in-progress" tests) with a final oral exam. Each written test typically consists of 8-10 open-ended questions taken from the exercises in the textbook (Carey & Sundberg, Part B; see Reference Materials). The exercises are similar to or of comparable difficulty to those done during the exercises. In general, the "in-progress" tests last 3 hours. The grade is on a scale of 30, corresponding to a detailed assessment of the skills acquired by the student. The results of the "in-progress" tests are posted anonymously on the notice board (only the student's registration number). The final oral exam (grade in thirtieths) is mainly focused on a discussion of the written tests.
CHEM-05/A - Organic Chemistry - University credits: 9
Exercises: 48 hours
Lessons: 48 hours
Lessons: 48 hours
Professors:
Fasano Valerio, Pignataro Luca Luigi
Shifts:
Professor(s)
Reception:
Tuesday from 10:30 to 12:30
Room 2042, second floor of the Chemistry building (Corpo B)