Course Syllabus for English-Taught Majors

Organic Chemistry Course Syllabus

 

Course Code09041039

Course CategoryMajor Basic

MajorsIntensive training class

SemesterSpring

Total Hours90 Hours         Credit3

Lecture Hours90 Hours 

InstructorsWang, Xing-Wang

TextbooksT. W. Graham Solomons, Craig B.Fryhle, Organic Chemistry(10 edition), John Wiley & Sons (Asia) Pte Ltd2011.

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 1 Carbon Compounds and Chemical Bonds 
1.1 Introduction 
1.2 The development of organic chemistry as a science 
1.3 The structural theory of organic chemistry
1.5Chemical bonds: The Octet rule
1.5 Writing lewis structures
1.6 Exceptions to the Octet Rules
1.7 Formal charge
1.8 Resonane
1.9 Quantum mechanics
1.10Atomic orbitals
1.11Molecular orbitals
1.12The structure of methane and ethane: sp3 hybridization
1.13The structure of ethane (ethylene): sp2 hybridization 
1.14 The structure of ethyne(acetylene): sp hybridization
1.15 A summary of important concepts that come from quantum mechanics
1.16  Molecular geometry: the valence shell electron pair repulsion model
1.17 Representation of structural formulas
Chapter 2 Representative Carbon Compounds: Fundctional Groups, Intermolecular Forces, and Infrared Spectroscopy 

2.1 Carbon-carbon covalent molecules

2.2 Hydrocarborns: representative alkanes, alkenes, alkynes, and aromatic compounds

2.3 Polar covalent bonds

2.4 Polar and nonpolar molecules

2.5 Functional groups

2.6 Alkyl halides or haloalkanes

2.7 Alcohols

2.8 Ethers

2.9 Amines

2.10 Aldehydes and ketones

2.11Carboxylic acidsesters, and amides

2.12Nitriles

2.13 Summary of important families of organic compounds

2.14 Physical properties and molecular structure

2.15 Summary of attractive electric forces

2.16 Infrared spectroscopy: an instrumental method for detecting functional groups

Chapter 3 An Introduction to Organic Reactions: Acids and Bass  

3.1 Reactions and their mechanisms

3.2 Acid-Base reactions

3.3 Heterolysis of bounds to carboncarbocations and carbanions

3.4  The use of curved arrows in illustrating reactions

3.5 The strength of acids and bases: Ka and pKa

3.6Predicting the outcome of acid-base reactions

3.7 The relationship between structure and acidity

3.8     Energy changes

3.9     The relationship between the equilibrium constant and the standard free-energy change Go

3.10    The acidity of carboxylic acids

3.11    The effect of the solvent onacidity

3.12    Organic compounds as bases

3.13    A mechanism for an organic reaction

3.14    Acids and bases in nonaqueous solutions

3.15    Acids-base reactions and the synthesis of deuterium and tritium-labeled compounds

Chapter 4 Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Syntesis 

4.1     Introduction to alkanes and cycloalkanes

4.2     Shapes of alkanes

4.3     Iupac nomenclature of alkanes, alkyl halides, and alcohols

4.4     Nomenclature of cycloalkanes

4.5     Nomenclature of alkanes and cycloalkanes

4.6     Nomenclature of alkynes

4.7     Physical properties of alkanes and cycloalkanes

4.8     Sigma bounds and bound rotation

4.9     Conformational analysis of butane

4.10    The relative stabilities of cycloalkanes: ring strain

4.11    The origin of ring strain in cyclopropane and cyclobutane: angle strain and trosional strain

4.12    Conformations of cyclohexane

4.13    Substituted cyclohexanesaxial and equatorial hydrogen atoms

4.14    Disubstituted cycloalkanes: cis-trans isomerism

4.15    Bicylic and polycyclic alkanes

4.16    Chemical reactions of alkanes

4.17    Synthesis of alkanes and cycloalkanes

4.18    Some general principles of structure and reactivity: a look toward synthesis

4.19    An introduction to organic synthsis

Chapter 5 Stereochemistry: Chiral Molecules

5.1     The biological significance of chirality

5.2     Isomerism: constitutional isomers and stereoisomers

5.3     Enantiomers and chiral molecules

5.4     More about the biological importance of chirality

5.5     Historical origin of stereochemistry

5.6     Tests for chirality: planes of symmetry

5.7     Nomenclature of enantiomers: the R & S system

5.8     Properties of enantiomers: optical activity

5.9     The origin of optical activity

5.10    The synthesis of chiral molecules

5.11    Chiral drugs

5.12    Molecules with more than one stereogenic center

5.13    Fischer projection formulas

5.14    Stereoisomerism of cyclic compounds

5.15    Relating configurations through reactions in which no bonds to the stereogenic carbon are broken

5.16    Separation of enantiomers: resolution

5.17    Compounds with stereogenic centers other than carbon

5.18   Chiral molecules that do not possess a tetrahedral atom with four different groups
Chapter 6 Lonic Reactions-Mucleophilic Substitution

6.1     Introduction

6.2     Nucleophilic substitution reactions

6.3     Nucleopiles

6.4     Leaving groups

6.5     Kinetics of a nucleophilic substitution reaction: an Sn2 reaction

6.6     A mechanism for the Sn2 reaction

6.7     Transition state theory: free-energy diagrams

6.8     The stereochemistry of Sn2 reaction

6.9     The reaction of tert-butyl chloride with hydroxide ion: an Sn1 reaction

6.10    A mechanism for the Sn1 reaction

6.11    Carbocations

6.12    The stereochemistry of Sn1 reaction

6.13    Factors affecting the rates of Sn1 and Sn2 reaction

6.14    Organic synthesis: functional group transformations using Sn2 reaction

6.15    Elimination reaction of alkyl halides

6.16    The E2 reaction

6.17    The E1 reaction

6.18    Substitution versus elimination

6.19    Overall summary

Chapter 7 Alkenes and Alkynes: Properties and Synthesis. Elimination Reactions of Alkyl Halides 

7.1     Introduction

7.2     The (E)-(Z) system for designating alkene diastereomers

7.3     Relative stabilities of alkenes

7.4     Cycloalkenes

7.5     Synthesis of alkenes via elimination reactions

7.6     Dehydrohalogenation of alkyl halides

7.7     Acid-Catalyzed dehydration of alcohols

7.8     Carbocation stability and occurrence of molecular rearrangements

7.9     Synthesis of alkynes by elimination reactions

7.10    The acidity of terminal alkynes

7.11    Replacement of terminal alkynes

7.12    Hydrogenation of alkenes

7.13    Hydrogenation: the function of the catalyst

7.14    Hydrogenation of alkynes

7.15    Structural information from molecular formulas and the index of hydrogen deficiency

Chapter 8 Alkenes and Alkynes II: Addition Reactions 

8.1     Introduction: addition to alkenes

8.2     Addition of hydrogen halides to alkenes: markovnikov’s rule

8.3     Stereochemistry of the ionic addition to an alkene

8.4     Addition of sulfuric acid to alkenes

8.5     Addition of water to alkenes: acid-catalyzed hydration

8.6     Alcohols from alkenes through oxymercuration-demercuration: markovnikov addition

8.7     Alcohols from alkenes through hydroboration-oxidation: anti-markovnikov syn hydration

8.8     Hydroboration: synthesis of alkylborances

8.9     Oxidation and hydrolysis of alkyborances

8.10    Summary of alkene hydration methods

8.11    Protonolysis of alkyborances

8.12    Addition of bromine and chlorine to alkenes

8.13    Stereochemistry of the addition of halogens to alkenes

8.14    Halohydrin formation

8.15    Divalent carbon compounds: carbenes

8.16    Oxidations of alkenes: syn 1,2-dihydroxylation

8.17    Oxidative cleavage of alkenes

8.18    Addition of bromine and chlorine to alkynes

8.19    Addition of hydrogen halides to alkynes

8.20    Oxidative cleavage of alkynes

8.21    Synthesis strategies revisited

Chapter 9 Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination 

9.1     Introduction

9.2     The electromagnetic spectrum

9.3     Nuclear magnetic resonance spectroscopy

9.4     Nuclear spin: the origin of the signal

9.5     Shielding and deshielding of protons

9.6     The chemical shift

9.7     Chemical shift equivalent and nonequivalent protons

9.8     Signal splitting: spin-spin coupling

9.9     Proton NMR spectra and rate processes

9.10    Carbon-13 NMR spectroscopy

9.11    Two-dimensional (2D) NMR techniques

9.12    An introduction to mass spectrometry

9.13    The mass spectrometer

9.14    The mass spectrum

9.15    Determination of molecular formations and molecular weights

9.16    Fragmentation

9.17    GC/MS analysis

9.18    Mass spectrometry of biomolecules

Chapter 10 Radical Teactions 

10.1    Introduction

10.2    Homolytic bond dissociation energies

10.3    The reaction of alkanes with halogens

10.4    Chlorination of methane: mechanism of reaction

10.5    Chlorination of methane: energy changes

10.6    Halogenation of higher alkanes

10.7    The geometry of alkyl reaicals

10.8    Reactions that generate tetrahedral stereogenic carbons

10.9    Radical addition to alkenes: the anti-markovbikov addition of hydrogen bromide

10.10   Radical polymerization of alkenes: chain-growth polymers

10.11   Other important radical reaction

Chapter 11 Alcohols and Ethers 

11.1    Structure and nomenclature

11.2    Physical properties of alcohols and ethers

11.3    Important alcohols and ethers

11.4    Synthesis of alcohols from alkenes

11.5    Reaction of alcohols

11.6    Alcohols as acids

11.7    Conversion of alcohols ioto alkyl halides

11.8    Alkyl halides from the reaction of alcohols with hydrogen halides

11.9    Alkyl halides from the reaction of alcohols with PBr3 or SOCl2

11.10   Tosylates, mesylates,and triflates: leaving group derivatives of alcohols

11.11   Synthesis of ethers

11.12   Reactions of ethers

11.13   Epoxides

11.14   Reactions of epoxides

11.15   Anti 1,2-dihydroxylation of alkenes via epoxides

11.16   Crown ethers: nucleophilic substitution reactions in relatively nonpolar aprotic solvents by phase-transfer catalysis

11.17   Summary of reactions of alkenes, alcohols, and ethers

Chapter 12 Alcohols for Carbonyl Compounds. Oxidation-Reduction and Organometallic Compounds 

12.1    Introduction

12.2    Oxidation-reduction reactions in organic chemistry

12.3    Alcohols by reduction of carbonyl compounds

12.4    Oxidation of alcohols

12.5    Organometallic compounds

12.6    Prepration of organolithium and organomagnesium compounds

12.7    Reactions of organolithium and organomagnesium compounds

12.8    Alcohols from grignard reagents

12.9    Lithium dialkylcuprates: the corey-posner, whitesides-house synthesis

12.10   Protecting groups

Chapter 13 Conjugated Unsaturated Systems 

13.1    Introduction

13.2    Allylic substitution and the allyl radical

13.3    The stability of the ally radical

13.4    The ally cation

13.5    Summary of rules for resonane

13.6    Alkadienes and polyunsaturated hydrocarbons

13.7    1,3-butadienes: electron delocalization

13.8    The stability of conjugated hydrocarbons

13.9    Ultravioler-visible spectroscopy

13.10   Electrophilic attack on conjugated dienes: 1,4 addition

13.11   The diels-alder reaction: a 1,4-cycloaddition reaction of dienes

Lecture assignment table:

Chapter

Contents

Lecture hours

1

Introduction And Chap. 1 Carbon Compounds and Chemical Bonds

8

2

Representative Carbon Compounds

8

3

An Introduction to Organic Reactions

6

4

Alkanes

8

5

Stereochemistry

6

6

Mucleophilic Substitution

8

7

Alkenes and Alkynes I

6

8

Alkenes and Alkynes II

8

9

Nuclear Magnetic Resonance and Mass Spectrometry

8

10

Radical Teactions

6

11

Alcohols and Ethers

8

12

Alcohols for Carbonyl Compounds

6

13

Conjugated Unsaturated Systems

8

summary

90

Assessment Methods

close-book examination

 

 

                                Made by Wang, Xing-Wang

                                                      Date:  6, Oct. 2016