Syllable: Organic Chemistry 1

 

Code: 0704095

Type: Compulsory

Composition: Theory (56 class hours)

Credit: 3.5

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 1. Introduction and Review

4

2

Chapter 2. Structure and Properties of Organic Molecules

4

3

Chapter 3. Structure and Stereochemistry of Alkanes

8

4

Chapter 4. The Study of Chemical Reactions

4

5

Chapter 5. Stereochemistry

10

6

Chapter 6. Alkyl Halides: Nucleophilic Substitution and Elimination

10

7

Chapter 7. Structure and Synthesis of Alkenes

6

8

Chapter 8. Reactions of Alkenes

10

 

 

Teaching contents:

Chapter 1. Introduction and Review

  • The origins of organic chemistry
  • Principles of atomic structure
  • Bond formation: the octet rule
  • Lewis structures
  • Multiple bonding
  • Structrual formulas
  • Arrhenius acids and bases
  • Lewis acids and bases

 

Chapter 2. Structure and Properties of Organic Molecules

  • Pi bonding
  • Hybridization and molecular shapes
  • Drawing three-dimensional molecules
  • General rules of hybridization and geometry
  • Bond rotation
  • Isomerism
  • Polarity of bonds and molecules
  • Intermolecular forces
  • Polarity effects on solubilities

 

Chapter 3. Structure and Stereochemistry of Alkanes

  • Physical properties of alkanes
  • Uses and sources of alkanes
  • Reactions of alkanes
  • Structure and conformations of alkanes
  • Cycloalkanes
  • Cyclohexane conformations
  • Conformations of monosubstituted cyclohexanes
  • Confromations of disubstituted cyclohexanes

 

Chapter 4. The Study of Chemical Reactions

  • Chlorination of methane
  • The free-radical chain reaction
  • Activation energy and the temperature dependence of rates
  • Transition states
  • Temperature dependence of halogenation
  • Selectivity in halogenation
  • The Hammond postulate

 

Chapter 5. Stereochemistry

  • Chirality
  • (R) and (S) nomenclature of asymmetric carbon atoms
  • Optical activity
  • Racemic mixtures
  • Enantiomeric excess and optical purity
  • Chirality of conformationally mobile systems
  • Chiral compounds without asymmetric atoms
  • Fischer projections
  • Diastereomers
  • Stereochemistry of molecules with two or more asymmetric carbons
  • Meso compounds
  • Absolute and relative configuration
  • Physical properties of diastereomers
  • Resolution of enantiomers

 

Chapter 6. Alkyl Halides: Nucleophilic Substitution and Elimination

  • Common uses of alkyl halides
  • Structure of alkyl halides
  • Physical properties of alkyl halides
  • Preparation of alkyl halides
  • Reactions of alkyl halides: substitution and elimination
  • Second-order nucleophilic substitution: the SN2 reaction
  • Generality of the SN2 reaction
  • Factors affecting SN2 reaction: strength of the nucleophile
  • Reactivity of the substrate in SN2 reactions
  • Stereochemistry of the SN2 reaction
  • First-order nucleophilic substitution: the SN1 reaction
  • Stereochemistry of the SN1 reaction
  • Rearrangement in SN1 reactions
  • Comparison of SN1 and SN2 reactions
  • First-order elimination: the E1 reaction
  • Positional orientation of elimination: Zaitsev’s rule
  • Second-order elimination: the E2 reaction
  • Stereochemistry of the E2 reaction
  • Comparison of E1 and E2 elimination mechanisms

 

Chapter 7. Structure and Synthesis of Alkenes

  • The orbital description of the alkene double bond
  • Elements of unsaturation
  • Commercial importance of alkenes
  • Stability of alkenes
  • Physical properties of alkenes
  • Alkene synthesis by elimination of alkyl halides
  • Alkene synthesis by dehydration of alcohols
  • Alkene synthesis by high-temperature industrial methods

 

Chapter 8. Reactions of Alkenes

  • Reactivity of the carbon-carbon double bond
  • Electrophilic addition to alkenes
  • Addition of hydrogen halides to alkenes
  • Addition of water: hydration of alkenes
  • Hydration by oxymercuration-demercuration
  • Hydroboration of alkenes
  • Addition of halogens to alkenes
  • Formation of halohydrins
  • Catalytic hydrogenation of alkenes
  • Addition of carbenes to alkenes
  • Epoxidation of alkenes
  • Syn hydroxylation of alkenes
  • Oxidative cleavage of alkenes
  • Polymerization of alkenes

 

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。