Syllable: Organic Chemistry 2

 

Code: 0704095

Type: Compulsory

Composition: Theory (96 class hours) + Experiments (40 class hours)

Credit: 8.5

Objective: International students

 

Goal:

  • The goal of Theoretical Organic Chemistry is to help students to master aspects of organic chemistry as a basic course for pharmacy students, including nomenclature, structures, physical properties, chemical reactions, mechanisms and synthesis of organic compounds.
  • In addition to Theoretical Organic Chemistry, Experimental Organic Chemistry is also an integral and basic part of Organic Chemistry course. Experimental Organic Chemistry is designed to familiarize the students with skills and techniques in organic chemistry, which will also deepen their understanding of related theories and principles.
  • The study of Organic Chemistry lays a foundation for study of subsequent courses such as Medicinal Chemistry.

 

Evaluation:

Attendance (10%) + Homework (10%)+ Pop quiz (10%) + Experiment (10%) + examinations (60%) = Overall score.

 

Course Schedule

Entry (Theoretical)

Content

Class hours

1

Chapter 10. Alkynes

6

2

Chapter 11. Conjugated systems

6

3

Chapter 12. Structure and synthesis of alcohols

6

4

Chapter 13. Reactions of alcohols

6

5

Chapter 14. Ethers and Epoxides

6

6

Chapter 15. Aromatic compounds

6

7

Chapter 16. Reactions of aromatic compounds

6

8

Chapter 17. Ketones and aldehydes

8

9

Chapter 18. Amines

8

10

Chapter 19. Carboxylic acids

6

11

Chapter 20. Carboxylic acid derivatives

6

12

Chapter 21. Condensations and alpha substitutions of carbonyl compounds

8

13

Chapter 22. Carbhydrates and Nucleic Acids

6

14

Chapter 23. Amino Acids, Peptides, and Proteins

6

15

Chapter 24. Lipids

6

Entry

(Experimental)

Content

Class hours

1

Simple distillation

4

2

Recrystallization

4

3

Melting point determination

3

4

Solvent extraction and solution washing

4

5

Preparation of dibutyl ether

5

6

Preparation of aspirin

5

7

Preparation of n-butyl acetate

5

8

Preparation of acetanilide

5

9

Synthesis of methyl orange

5

 

 

Teaching contents:

Chapter 10. Alkynes

  • Nomenclature of alkynes
  • Physical properties of alkynes
  • Electronic structure of alkynes
  • Acidity of alkynes; formation of acetylide ions
  • Synthesis of alkynes: from acetylides; by elimination reactions
  • Addition reactions of alkynes
  • Oxidation of alkynes

 

Chapter 11. Conjugated systems

  • Structure and stability of dienes
  • Allylic cations
  • 1,2- and 1,4-addition to conjugated dienes
  • Kinetic versus thermodynamic control in the addition of HBr to 1,3-butadiene
  • Allylic radicals
  • The Diels-Alder reaction

 

Chapter 12. Structure and synthesis of alcohols

  • Structure and classification of alcohols
  • Physical properties of alcohols
  • Acidity of alcohols and phenols
  • Synthesis of alcohols: summary of previous methods
  • Addition of organometallic reagents to carbonyl compounds
  • Reduction of the carbonyl group: synthesis of 1° and 2° alcohols
  • Thiols

 

Chapter 13. Reactions of alcohols

  • Oxidation states of alcohols and related functional groups
  • Oxidation of alcohols
  • Alcohols as nucleophiles and electrophiles: formation of tosylates
  • Reduction of alcohols
  • Dehydration reactions of alcohols
  • Unique reactions of diols

 

Chapter 14. Ethers and Epoxides

  • Nomenclature of ethers, and epoxides
  • Synthesis of ethers: the Williamson ether synthesis; bimolecular dehydration of alcohols
  • Cleavage of ethers by HBr and HI
  • Autoxidation of ethers
  • Synthesis of epoxides
  • Ring opening of epoxides: acid-catalyzed; base-catalyzed

 

Chapter 15. Aromatic compounds

  • The structure and properties of benzene
  • Aromatic compounds and Huckel’s rule
  • Nomenclature of benzene derivatives

 

Chapter 16. Reactions of aromatic compounds

  • Electrophilic aromatic substitution: Halogenation; nitration; sulfonation
  • Activating, ortho, para-directing substituents
  • Deactivating, meta-directing substituents
  • Deactivating, but ortho, para-directing substituents
  • Effects of multiple substituents on EAS
  • The Friedel-Crafts alkylation and acylation
  • Nucleophilic aromatic substitution
  • Addition reactions of benzene derivatives
  • Side-chain reactions of benzene derivatives
  • Reactions of phenols

 

Chapter 17. Ketones and aldehydes

  • Structure of the carbonyl group
  • Nomenclature of ketones and aldehydes
  • Physical properties of ketones and aldehydes
  • Review of synthesis of ketones and aldehydes
  • Reactions of ketones and aldehydes: Nucleophilic addition
  • Hydration of ketones and aldehydes; formation of cyanohydrins; formation of acetals; formation of imines
  • Oxidation of aldehydes
  • Reductions of ketones and aldehydes

 

Chapter 18 Amines

  • Structure and nomenclature of amines
  • Physical properties of amines
  • Basicity of amines
  • Reactions of amines with ketones and aldehydes (review); aromatic substitution of arylamines (review)
  • Alkylation of amines by alkyl halides
  • Acylation of amines by acid chlorides
  • Formation of sulfonamides
  • The Hofmann elimination
  • Reactions of amines with nitrous acid
  • Reactions of arenediazonium salts
  • Synthesis of amines: by reductive amination; by acylation-reduction

 

Chapter 19 Carboxylic acids

  • Structure, nomenclature, and physical properties of carboxylic acids
  • Acidity of carboxylic acids
  • Synthesis of carboxylic acids
  • Reactions of carboxylic acids and derivatives
  • Condensation of acids with alcohols: esterification
  • Condensation of acids with amines
  • Reduction of carboxylic acids
  • Alkylation of carboxylic acids to form ketones
  • Synthesis and use of acid chlorides

 

Chapter 20 Carboxylic acid derivatives

  • Structure, nomenclature, and physical properties of carboxylic acid derivatives
  • Interconversion of acid derivatives
  • Transesterification
  • Hydrolysis of carboxylic acid derivatives
  • Reduction of acid derivatives
  • Reactions of acid derivatives with organometallic reagents

 

Chapter 21 Condensations and alpha substitutions of carbonyl compounds

  • Enols and enolate ions
  • Alpha halogenations of ketones
  • a bromination of acids
  • Alkylation of enolate ions
  • Formation and alkylation of enamines
  • The aldol condensation of ketones and aldehydes
  • Dehydration of aldol products
  • Crossed aldol condendations
  • Aldol cyclizations
  • The Claisen ester condensation and the Dieckmann condensation
  • Crossed Claisen condensations
  • Syntheses using b-dicarbonyl compounds
  • The malonic ester synthesis
  • The acetoacetic ester synthesis
  • Conjugate additions: the Michael reaction
  • The Robinson annulation

 

Chapter 23 Carbohydrates and nucleic acids

  • Classification of carbohydrates
  • Monosaccharides
  • Erythro and threo diastereomers
  • Epimers
  • Cyclic structures of monosaccharides
  • Anomers of monosaccharides
  • Reduction of monosaccharides
  • Oxidation of monosaccharides; reducing sugars
  • Nonreducing sugars: formation of glycosides
  • Disaccharides and polysaccharides
  • Ribonucleosides and bibonucleotides
  • The structure of ribonucleic acid
  • Deoxyribose and the structure of deoxyribonucleic acid

 

Chapter 24 Amino acids, peptides, and proteins

  • Structure and stereochemistry of the a-amino acids
  • Acid-base properties of amino acids
  • Isoelectric points and electrophoresis
  • Synthesis of amino acids
  • Reactions of amino acids
  • Structure and nomenclature of peptides and proteins
  • Peptide structure determination
  • Classification of proteins
  • Levels of protein structure
  • Protein denaturation

 

Chapter 25. Lipids

  • Waxes
  • Triglycerides
  • Saponification of fats and oils
  • Phospholipids
  • Steroids
  • Prostaglandins
  • Terpenes

 

Reference book

  • Organic Chemistry, six edition, L.G. Wade, Jr., Pearsonn Education International, 2006.
  • Experimental Organic Chemistry, second edition, 薛思佳、季萍、Larry Olson,科学出版社,2011年。