Organic Chemistry II - MC270P108B

• Title: Organic Chemistry II
• Czech title: Organická chemie II (v angličtině)
• Guaranteed by: Department of Organic Chemistry (31-270)
• Faculty: Faculty of Science
• Actual: from 2023
• Semester: summer
• E-Credits: 5
• Examination process: summer s.:
• Hours per week, examination: summer s.:3/2, C+Ex [HT]
• Capacity: unlimited
• Min. number of students: unlimited
• 4EU+: no
• Virtual mobility / capacity: no
• State of the course: taught
• Language: English
• Note: enabled for web enrollment
• Guarantor: Dr. Lukáš Rýček, M.Sc.
• Teacher(s): Dr. Lukáš Rýček, M.Sc.; Mykyta Ziabko
• Incompatibility : MC270P61A, MC270P76, MC270P80

Annotation

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.02.2022)

The aim of the course is to provide students with the basic knowledge of organic chemistry. Basic reactivity of
selected organic compounds (including carbonyl compounds such as aldehydes ketones, carboxylic acid and
derivatives, amines, aminoacids, and sugars), will be discussed as well as pericyclic reactions.

Literature

Last update: PharmDr. Eliška Matoušová, Ph.D. (23.05.2022)

1. J. McMurry - Organic Chemistry, 8th ed., Brooks/Cole, 2012

2. S. McMurry - Organic Chemistry Study Guide and Solution Manual, 8th ed., Brooks/Cole, 2011

Requirements to the exam

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.02.2022)

The credits from the tutorial course are needed for enrolling for the exam.

The exam will be in the written form, covering the material discussed during the lectures and included in the recommended literature.

The conditions for successful fulfilling of the tutorial lectures are as follows:

• 70% attendance (in case of absence higher then 30%, it is necessary to rationalize the absence by a medical or other document)

• Working out four homeworks.

• Passing a final test with at least 60%.

Syllabus

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.02.2022)

1. Aldehydes and ketones: preparation, reactivity oxidation of aldehydes, relative reactivity. Nucleophilic addition to aldehydes and ketones: hydration, addition of HCN, addition of organometallic species, addition of amines and hydrazines.

2. Other reactions involving attack of the carbonyl carbon: reduction of karbonyl to alkanes (Wolff-Kischner reaction, Clemmenson reduction), conversion of carbonyl compounds to alkenes (Wittig olefination, Peterson olefination, Tebbe reaction).

3. Carboxylic acids and nitriles. Physical properties of carboxylic acids. The influence of the structure on the acidity of carboxylic acids. Preparation of the carboxylic acids (, benzylic oxidation, oxidative cleavage of alkenes, oxidation of alcohols and aldehydes, hydrolysis of nitriles, carboxylation of Grignard reagents, haloform reaction, Kolbe-Schmitt reaction, Arndt-Eistert reaction, Favorski rearrangement. Reactions of carboxylic acids: reduction. Preparation of nitriles by dehydration of amides. Reaction of nitriles: addition of water, organometallic reagents, reduction.

4. Carboxylic acid derivatives. Nucleophilic acyl substitution. Relative reactivity of carboxylic derivatives. Preparation of acyl halides, esters and amides from carboxylic acids. Reaction of acyl halides, Chemistry of acid anhydrides, chemistry of esters and amides

5. Keto-enol tautomerism (acid and base catalyzed). Enol reactivity and mechanism of alpha-substitution. Alpha-halogenation of aldehyde and ketons (Favorski rearrangement), of carboxylic acids (Hell-Volhard-Zielinski). Acidity of alpha hydrogens in carbonyl compounds, enolates and their reactivity: halogenation, haloform reaction, alkylation (malonester, acetoacetate syntheses). Kinetic and thermodynamic alkylation of enolates.

6. Condenstaion of carbonyl compounds. Condensation of aldehydes and ketones, enolization enone formation, mixed aldol reactions, Mukaiyama aldol reaction. Intramolecular aldol condemsation. Claissen condensation, mixed Claissen condensation, Diecmann condensation, Sobbe condensation, Knoevenagel condensation, Michael addition, Robinson annelation, Wieland-Miescher and Hajos-Parrish Ketones. Stork reaction.

7. Amines and their bondin arrangments. Physical properties of amines. Basicity of various amines. Preparatiopn of amines (nitrile reduction, , reduction of nitro compounds, substitution reactions, Sandmayer reaction, synthesis via azides, Gabriel synthesis, erductive amination, Delephin reaction). Hofmann and Curtius rearrangement, Hofmann elimination, Electrophylic aromatic substitution of aryamines, Diazonium salts.

8. Saccharides. Classification of sacharides, cyclic and linear structure of sacharides. Anomers and mutarotation. Reactions of monosaccharides: esterification, formation of ethers. , Williams reaction, Koenigs-Knorr reaction and its mechanism. Reductions and oxidations of sugars. Chain elongation and shortening (Kiliani-Fisher reaction and Wohl reaction). Disacharides, polysaccharides, deoxysacharides, aminosacharides, ascorbic acid.

9. Aminoacids, peptides and proteins. Structure of aminoacids, Fisher projection, Isoelectric point, Aminoacid synthesis, peptides and proteins. Peptide covalent bond. Structure of peptides and its determination (Edman degradation). Synthesis of peptides (Merryfield synthesis). Structure of proteins.

10. Biomolecules and lipids. Soups, prostaglandins, terpenoids, steroids and their structure. Heterocyclic compounds. Five and six-membered heterocycles and their reactions. Nucelosides, nucleotides and nucleic acids.

11. Pericyclic reactions. Classification of pericyclic reactions (electrocyclic, cycloadditions, sigmatropic rearrangement). Molecular orbitals. Frontier orbitals. Stereochemistry of electrocyclic reactions under thermal and light driven reactions. Cycloadditions: Diels-Alder reaction, [2+2]-cycloadditions. Sigmatropic rearrangement, clasification and examples (Claisen rearrangement, Cope rearrangement).