Organic Chemistry II

The aim of lectures and seminars is to familiarize the student with basic knowledge in the field of organic chemistry, allowing to discuss the structure of organic compounds (taking into account their spatial structure) and their physical and chemical properties. Tthe mechanisms of basic reactions will be explained during the lectures. The aim of the laboratories is to familiarize the student with the basic techniques of isolation and purification of organic compounds. During the classes, the student should master the manual skills necessary for laboratory work, learn how to plan and observe experiments, draw conclusions from them and write reports. The students should familiarize themselves with safety regulations, in particular with the principles of safe use of chemicals and disposal of chemical waste. In addition, these classes should teach the student to plan and organize their own working time, independent problem solving, as well as working in a group.

1. Aldehydes and Ketones - nucleophilic addition reactions (addition of water, HCN, alcohol, nitrogen nucleophiles, complex metal hydride, and Grignard reagents. Nucleophilic addition to alpha,beta-unsaturated aldehydes and ketones; aldehyde and ketone synthesis methods; oxidation of Aldehydes and Ketones.

2. Carboxylic Acids and Nitriles; - structure and properties of Carboxylic Acids; substituent effects on acidity; carboxylic acid and nitrile synthesis method.

3. Carboxylic acid derivatives - nucleophilic acyl substitution reactions; chemistry of acyl halides, acid anhydrides, esters.

4. Carbonyl alpha-substitution reactions; keto-enol tautomerism; alpha halogenation of aldehydes and ketones - haloform reaction, alkylation.

5. Carbonyl condensation reactions - aldol reaction; dehydration of adol products - synthesis of enones; mixed adol reactions; Claisen condensation Dieckmann cyclization; conjugate carbonyl additions - Michael reaction;

6. Aliphatic and aromatic amines - structure and basicity of amines; reactions and synthesis methods of amines and arylamines.

7. Amides - Aamide synthesis; Beckmann rearrangement, Hofmann degradation; Curtius rearrangement; Gabriel synthesis

8. Heteroaromatic compounds; - the structure of furan, pyrrole, thiophene, and pyridine; synthesis of heterocyclic rings; electrophilic substitution reactions of heteroaromatic compounds; nucleophilic substitution of pyridine - Chichibabin reaction.

9. Biomolecules - carbohydrates, proteins, lipids.

Literature:

McMurry J., Fundamentals of Organic Chemistry, Pacific Grove, CA: Brooks/Cole Pub. Co., 1998.

Morrison R.T., Boyd R.N., Organic Chemistry, 7th edition, Pearson, 2008.

Hallas G. Organic Stereochemistry, McGraw-Hill. London, New York 1965.

Complementary literature:

Smith, M. B., March J., March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley-Interscience, 2001.

The aim of lectures and seminars is to familiarize the student with basic knowledge in the field of organic chemistry, allowing to discuss the structure of organic compounds (taking into account their spatial structure) and their physical and chemical properties. Tthe mechanisms of basic reactions will be explained during the lectures. The aim of the laboratories is to familiarize the student with the basic techniques of isolation and purification of organic compounds. During the classes, the student should master the manual skills necessary for laboratory work, learn how to plan and observe experiments, draw conclusions from them and write reports. The students should familiarize themselves with safety regulations, in particular with the principles of safe use of chemicals and disposal of chemical waste. In addition, these classes should teach the student to plan and organize their own working time, independent problem solving, as well as working in a group.

1. Aldehydes and Ketones- Nucleophilic Addition Reactions; Nucleophilic Addition of Water- Hydration; Nucleophilic Addition of HCN - Cyanohydrin Formation; Nucleophilic Addition of Hydride and Grignard Reagents - Alcohol Formation; Nucleophilic Addition of Amines - Imine and Enamine Formation; Nucleophilic Addition of Hydrazine - The Wolff-Kishner Reaction; Nucleophilic Addition of Alcohols - Acetal Formation; Conjugate Nucleophilic Addition to alpha, beta-unsaturated Aldehydes and Ketones; Preparing Aldehydes and Ketones, Oxidation of Aldehydes and Ketones.

2. Carboxylic Acids and Nitriles; Structure and Properties of Carboxylic Acids; Substituent Effects on Acidity; Preparing Carboxylic Acids.

3. Carboxylic Acid Derivatives- Nucleophilic Acyl Substitution Reactions; Chemistry of Acyl Halides, Acid Anhydrides and Esters.

4. Carbonyl Alpha-Substitution Reactions; Keto-Enol Tautomerism; Alpha Halogenation of Aldehydes and Ketones - Haloform Reaction.

5. Carbonyl Condensation Reactions - The Aldol Reaction; Dehydration of Aldol Products - Synthesis of Enones; Mixed Aldol Reactions; The Claisen Condensation Reaction; Intramolecular Claisen Condensations - The Dieckmann Cyclization; Conjugate Carbonyl Additions - The Michael Reaction; The Robinson Annulation Reaction.

6. Aliphatic and Aromatic Amines; Structure and Basicity of Amines; Reactions of Amines and Arylamines.

7. Amides; Preparing Amides; Beckmann rearrangement, Hofmann degradation of amides; Curtius Rearrangement; Gabriel Synthesis; Peptides.

8. Heteroaromatic Compounds; The Structure of Furan, Pyrrole, thiophene, and Pyridine; Synthesis of Heterocyclic Rings; Electrophilic substitution reactions of heteroaromatic compounds; Nucleophilic Substitution of Pyridine - Chichibarin Reaction.

9. Biomolecules - carbohydrates, proteins, lipids, Nucleic Acids.

Literature:

McMurry J., Fundamentals of Organic Chemistry, Pacific Grove, CA: Brooks/Cole Pub. Co., 1998.

Morrison R.T., Boyd R.N., Organic Chemistry, 7th edition, Pearson, 2008.

Hallas G. Organic Stereochemistry, McGraw-Hill. London, New York 1965.

Complementary literature:

Smith, M. B., March J., March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley-Interscience, 2001.