Course Syllabus for English-Taught Majors

Organic Chemistry Course Syllabus

 

Course Code09041040

Course CategoryMajor Basic

MajorsIntensive training class

SemesterFall

Total Hours90 Hours         Credit3

Lecture Hours4 Hours 

InstructorsWang, Xing-Wang

TextbooksT. W. Graham Solomons, Craig B.Fryhle, Organic Chemistry(10 edition), John Wiley & Sons (Asia) Pte Ltd, 2011.

References

1.Organic Chemistry, Jonathan Clayden, Nick Geeves, Stuart Warren, 2nd Edition, ISBN: 978-0199270293. Oxford University Press, 2012.

2. Organic Chemistry, Paula Y. Bruice, 6th Edition, ISBN: 978-0-321-66313-9, Prentice Hall, 2010.

3. Advanced Organic Chemistry, Francis A. Carey, Richard A. Sundberg, 5th Edition, ISBN-13: 978-0-387-44897-8, Springer, 2007.

4.  March's Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, Michael B. Smith, Jerry March, 6th Edition, ISBN: 978-0-471-72091-1, Wiley, 2007.

5.Organic Mechanisms - Reactions, Stereochemistry and Synthesis, Reinhard Brückner, First Edition, ISBN: 978-3-642-03650-7, Springer, 2010.

6.Classics in Total Synthesis: Targets, Strategies, Methods, Nicolaou, K. C.; Sorensen, E. J. ISBN 978-3-527-29231-8, Wiley, 1996.

7. Organic Reaction Mechanisms, M. Gomez Gallego, M. A. Sierra, First Edition, ISBN: 3-540-00352-5, Springer, Berlin, 2004.

8.Organic Chemistry, John McMurry, Sixth Edition, ISBN: 9780534389994 Brooks/Cole, 2004.

Teaching Aim

Organic chemistry is the chemistry of carbon and its compounds. These compounds are called organic molecules. Organic molecules constitute the chemical bricks of life. Fats, sugars, proteins, and the nucleic acids are compounds in which the principal component is carbon. So are countless substances that we take for granted in everyday use. All the clothes that we wear, toothbrushes, toothpaste, soaps, shampoos, deodorants, perfumes, contain organic compounds. Jöns Jacob Berzelius in 1807 coined the term "organic chemistry" for the study of compounds derived from natural sources. It was believed inorganic compounds could be synthesized in the laboratory, but organic compounds could not, at least not from inorganic materials. In 1828 Friedrich Wöhler, obseved one transformation in which an inorganic salt, amonium cyanate, was converted to urea, a known organic sustance earlier isolated from urine.

This class begin with the alkanes, organic compounds composed of only hydrogen and carbon and lacking functional groups. We discuss the systematic rules for naming them, their structures, and their physical properties. We shall then study the cycloalkanes which contain carbon atoms in a ring. Experimental evidence indicating that six-membered rings are nonplanar. The most stable conformation of cyclohexane is the chair conformation. The Stereochemistry study compounds that have the same constitution but differ in the spatial arrangement of their atoms. We shall then study substitution and elimination reations. In a substitution reaction, one halogen atom may be replaced by another group; in an elimination reaction, adjacent atoms may be removed from a molecule to generate a double bond. This class continues with the chemistry of alkenes, alkynes, alcohols, ethers, aldehydes and ketones, benzene, carboxilic acid, acyl halides, anhydrides, esters, amides, nitriles, amines, carbohydrates, amino acid. This book deals with about 100 of the most important reactions in organic chemistry; the selection is based on their importance for modern preparative organic chemistry. The reactions are arranged in alphabetical order.

Organic synthesis is a very important part of organic chemistry. More than 10 million organic substances have been synthesized from simpler materials, both organic and inorganic. The goal of synthesis is to construct complex organic chemicals from simpler, more readily available ones. To be able to convert one molecule into another, chemists must know organic reactions.

Contents:

Chapter 14 Aromation Compounds 

14.1    Introduction

14.2    Nomenclature of benzene derivatives

14.3    Reaction of benzene

14.4    The kekule structure for benzene

14.5    The stability of benzene

14.6    Modern theories of the structure of benzene

14.7    Huckel’s rule: the 4n+2 ∏ electron rule

14.8    Other aromatic compounds

14.9    Heterocylic aromatic compounds

14.10   Aromatic compounds in biochemistry

14.11   Spectroscopy of aromatic compounds

Chapter 15 Reactions of Aromatic Compounds 

15.1    Electrophilic aromatic substitution reactions

15.2    A general mechanism for elctrophilic aromatic substitution: arenium ions

15.3    Halogenation of benzene

15.4    Nitration of benzene

15.5    Sulfonation of benzene

15.6    Friedel-crafts alkylation

15.7    Friedel-crafts acylation

15.8    Limitations of friedel-crafts reactions

15.9    Synthesis applications of friedel-crafts acylations: the clemmensen reduction

15.10   Effect of substituents on reactivity and orientation

15.11   Theory of substituent effects on electrophilic aromatic substitution

15.12   Resctions of the side chain of alkylbenzenes

15.13   Alkenylbenzenes

15.14   Synthesis applications

15.15   Allylic and benzylic halides in nucleopilic substitution reactions

15.16   Reduction of aromatic compounds

Chapter 16 Aldehydes and Ketones 1. Nucleophilic Addition to the Carbonyl Group
16.1     Introduction 
16.2     Nomenclature of Aldehydes and Ketones
16.3     Physical Properties 
16.4     Synthesis of Aldehydes 
16.5     Synthesis of Ketones 
16.6     Nucleophilic     Additon to the Carbon-Oxygen Double Bond 
16.7    The Addition of Alcohols: Hemiacetals and Acetals 
16.8     The Addition of Primary and Secondary Amines 
16.9     The Addition of Hydrogen Cyanide 
16.10    The Addition of Ylides: The Witting Reaction 
16.11    The Addition of Organometallic Reagents: The Reformatsky Reaction 
16.12    Oxidation of Aldehydes and Ketones 
16.13    Chemical Analyses for Aldehydes and Ketones 
16.14    Spectroscopic Properties of Aldehydes and Ketones 
Chapter 17 Aldehydes and Ketones 2. Aldol Reactions 
17.1     The Acidity of the α Hydrogens of Carbonyl Compounds: Enolate Anions 
17.2     Keto and Enol Tautomers 
17.3     Reactions Via Enols and Enolate Anions 
17.4     The Aldol Reaction: The Addition of Enolate Anions to Aldehydes and Ketones 
17.5     Crossed Aldol Reactions 
17.6     Cyclizations via Aldol Condensations 
17.7     Lithium Enolates 
17.8     α-Selenation: A Synthesis of α, β-Unsaturated Carbonyl Compounds 
17.9     Additions to α, β-Unsaturated Carbonyl Compounds 
Chapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon 
18.1     Introduction 
18.2     Nomenclature and Physical Properties 
18.3     Preparation of Carboxylic Acids 
18.4     Nucleophilic Addition-Elimination at Acyl Carbon 
18.5     Acyl Chlorides
18.6     Carboxylic Acid Anhydrides 
18.7     Esters 
18.8     Amides 
18.9     Derivatives of Carbonic Acid
18.10    Decarboxylation of Carboxylic Acids 
18.11    Chemical Tests for Acyl Compounds 
Chapter 19 Synthesis and Reaction of β-Diccrbonyl Compounds: More Chemistry of Enolate ions 
19.1    Introduction 
19.2    The Claisen Condensation: The Synthesis of β-Keto Esters
19.3    The Acetoacetic Ester Synthesis of Methyl Kethones (Substituted Acetone) 
19.4    The Malonic Ester Synthesis: Synthesis of Substituted Acetic Acids 
19.5    Further Reactions of Active Hydrogen Compounds 
19.6    Direct Alkylation of Esters and Nitriles 
19.7    Alkylation of 1,3-Dithianes 
19.8    The Knoevenagel Condensation 
19.9    Michael Additions 
19.10   The Mannich Reaction 
19.11   Synthesis of Enamines: Stork Enamine Reactions 
19.12   Barbiturates 
Chapter 20 Amines 
20.1     Nomenclature 
20.2     Physical Properties and Structure of Amines 
20.3     Basicity of Amines: Amine Salt 
20.4     Some Biologically Important Amine 
20.5     Preparation of Amines 
20.6     Reactions of Amines 
20.7     Reactions of Amines with Nitrous Acid 
20.8     Replacement Reactions of Arenediazonium Salts
20.9     Coupling Reactions of Arenediazonium Salts 
20.10    Reactions of Amines with Sulfonly Chlorides 
20.11   The Sulfa Drugs: Sulfanilamide
20.12    Analysis of Amines 
20.13   Eliminations Involving Ammonium 
Chapter 21 Phenols and Aryl Halides: Nucleophilic Aromatic Substitution 
21.1    Structure and Nomenclature of Phenols 
21.2    Naturally Occurring Phenols 
21.3    Physical Properties of Phenols
21.4    Synthesis of Phenols 
21.5    Reactions of Phenols as Acids 
21.6    Other Reactions of the O-H Group of Phenols 
21.7    Cleavage of Alkyl Aryl Ethers 
21.8    Reactions of the Benzene Ring of Phenols
21.9    The Claisen Rearrangement 
21.10   Quinones 1015
21.11   Aryl Halides and Nucleopholic Aromatic Substitution
21.12   Spectroscopic Analysis of Phenols and Aryl Halides
Chapter 22 Carbohydrates 
22.1    Introduction 
22.2    Monsaccharides 
22.3    Mutarotation 
22.4    Glycoside Formation 
22.5    Other Reactions of Monosaccharides 
22.6    Oxidation Reactions of Monosaccharides
22.7    Reduction of Monosaccharides: Alditols 
22.8    Reactions of Monosaccharides with Phenylhydrazine : Osazone 
22.9    Synthesis and Degradstion of Monosaccharides 
22.10   The D Family of Aldoses 
22.11   Fischer’s Proof of the Configuration of D-(+)-Glucose 1099
22.12   Disaccharides 
22.13   Polysaccharides
22.14   Other Biologically Important Sugars
22.15   Sugars that Contain Nitrogen 
22.16   Glycolipids and Glycoproteins of the Cell Surface: Cell Recognition and the Immune System 
22.17   Carbohydrate Antibiotics
Chapter 23 Lipids 
23.1    Introduction
23.2    Fatty Acids and Triacylglycerols
23.3    Terpenes and Terpenoids 
23.4    Steroids 
23.5    Prostaglandins 
23.6    Phospholipids and Cell Membranes 
23.7    Waxes 
Chapter 24 Amino Acids and Proteins 
24.1    Introduction 
24.2    Amino Acids 
24.3    Synthesis of α- Amino Acids 
24.4    Polypeptides and Proteins 
24.5    Primary Structure of Polypeptides and Proteins 
24.6    Examples of Polypeptide and Protein Primary Structure
24.7    Polypeptide and Protein Synthesis 
24.8    Secondary, Tertiary, and Quaternary Structure of Proteins 
24.9    Introduction to Enzymes 
24.10   Lysozyme: Mode of Action of an Enzyme 
24.11   Serine Proteases 
24.12   Hemoglobin: A Conjugated Protein 
24.13   Purification and Analysis of Polypeptides and Proteins
24.14   Proteomics 
Chapter 25 Nucleic Acids and Protein Synthesis 
25.1    Introduction 
25.2    Nucleotides and Nucleosides and Nucleotides
25.3    Laboratory Synthesis of Nucleosides and Nucleotides
25.4    Deoxyribonucleic Acid: DNA
25.5    RNA and Protein Synthesis 
25.6    Determining the Base Sequence of DNA: the Chain Terninating(Dideoxynucleotide Method) 
25.7    Laboratory Synthesis of Oligonucleotides
25.8    The Polymerase Chain Reaction 
25.9    Sequencing of the Human Genome: An Instruction Book for the Molecules of Life 1251

Lecture assignment table:

Chapter

Contents

Lecture hours

14

 Aromation Compounds

6

15

 Reactions of Aromatic Compounds

6

16

Aldehydes and Ketones 1. Nucleophilic Addition to the Carbonyl Group

6

17

Aldehydes and Ketones 2.Aldol Reactions

8

18

Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon

6

19

Synthesis and Reaction of β-Diccrbonyl Compounds: More Chemistry of Enolate ions

8

20

Amines

6

21

Phenols and Aryl Halides : Nucleophilic Aromatic Substitution

8

22

Carbohydrates

6

23

Lipids

6

24

Amino Acids and Proteins

6

25

Nucleic Acids and Protein Synthesis

6

summary

72

 

Assessment Methods

close-book examination

 

 

                                Made by Wang, Xing-Wang

                                                      Date:  6, Oct. 2016