Organic Chemistry Fall, 2006 by 駱碧秀老師 Time: Tue. 08:10-10:00 & Wed. 13:00-14:00 Office: 醫學大樓 5F, 分機 Office Hours: Tuesday 10:10-12:00 am

Lecture & Assignment Schedule (NEW) WeekDate Topics 1 09/19,20 Introduction & Structure & Bonding (1) 2 09/26,27 Alkanes (2) 3 10/03,04 Alkenes (3) 4 10/10,11 Reaction of Alkenes & Alkynes (4) 5 10/17,18 Aromatic Compounds (5) 6 10/24 期中考 (I) (20%) 7 10/31,01 Stereochemistry (6) 8 11/07,08 Alkyl Halides (7) 9 11/14,15 Structure Determination (13) 10 11/21,22 Alcohols-1 (8) 11 11/28,29 Alcohols-2 (8) 12 12/05 期中考 (II) (20%) 13 12/12,13 Aldehydes & Ketones (9) 14 12/19,20Carboxylic Acids & Derivatives (10) 15 12/26,27Carbonyl Alpha-Substitution Reactions (11) 16 01/02,03Amines (12) 17 01/08,09Biomolecules: Proteins 18 01/16 期末考 (30%)

Lecture & Assignment Schedule WeekDate Topics 1 09/19,20 Introduction & 2 09/26,27Structure & Bonding (1) 3 10/03,04Alkanes (2) 4 10/10,11Alkenes (3) 5 10/17,18Reaction of Alkenes & Alkynes (4) 6 10/24,25Aromatic Compounds (5) 7 10/31,01Stereochemistry (6) 8 11/07,08Alkyl Halides (7) 9 11/14 期中考 10 11/21,22Structure Determination (13) 11 11/28,29Alcohols-1 (8) 12 12/05,06Alcohols-2 (8) 13 12/12,13Aldehydes & Ketones (9) 14 12/19,20Carboxylic Acids & Derivatives (10) 15 12/26,27Carbonyl Alpha-Substitution Reactions (11) 16 01/02,03Amines (12) 17 01/08,09Biomolecules: Proteins 18 01/16 期末考

Text Book “Fundamentals of Organic Chemistry” 6 th Edition, (Brooks/Cole Publishing Company ) 2006 by John McMurry

Grading 課程參與度 : 10% 平常小考 : 20% 期中考 : 30% 期末考 : 40% 「成績，不只是在於你知道什麼， 而在於你表現什麼。」 成功法則第一招：一定要來上課！

Chapter 1 Structure and Bonding; Acids and Bases

Chapter 1 Structure & Bonding What is organic Chemistry? treat illnesses, protect crops, & clean clothes

Why should we study it? Which elements in organic compounds?

Organic chemistry is the study of the compounds of carbon. Includes biological molecules, drugs, solvents, dyes Does not include metal salts and materials (inorganic) Does not include materials of large repeating molecules without sequences (polymers)

1.1 Atomic Structure Atom: (2x m) Nucleus Protons (+) ~ m neutrons Electrons (-) m

1.1 Atomic Structure Atomic number (Z) Mass number (A) Atomic weight Orbital (): s, p, d, & f. (fig. 1.4)

1.2 Electron Configuration of Atoms Ground-state electron configuration Rules 1-3 at page 4 See Table 1.1 as examples

1.3 Chemical Bonding Theory 2D to 3D Tetrahedral carbon atom

1.4 The Nature of Chemical Bonds Ionic Bonds Bond between ions due to the electrostatic attraction : NaCl Covalent Bonds Bonds formed by sharing electrons Lewis structures (electron-dot) Nonbonding electrons (lone-pair electrons)

1.4 The Nature of Chemical Bonds Lewis structures

Number of covalent bonds

Kekul é strutures (line-bond structure) Table The Nature of Chemical Bonds

1.5 Forming Covalent Bonds Valence Bond Theory How to electron sharing between atoms? Overlapping of two atomic orbital. Bond strength energy Bond length distance

1.5 Forming Covalent Bonds Molecular orbitals

1.6~1.8 Hybridization Hybridization: (1) SP 3 orbitals : Methane

Ethane: CH 3 -CH 3

1.8 Double and Triple Bonds

Ethylene C 2 H 4  bond P bond

Acetylene C 2 H 2 One -bond & two -bonds

1.9 Bond Polarity & Electronegativity Covalent bond to ionic bond EN =

1.9 Bond Polarity & Electronegativity Elctronegativity: ability of an atom to attract electrons in a covalent bond.

1.10 Bond Polarity & Electronegativity Electrostatic potential maps Electron rich (red) Electron poor (blue)

1.10~11 Acids & Bases Bronstered-Lowry definition Donates/accepts a hydrogen ion (H + ) Conjugate A/B

1.10~11 Acids & Bases Ka & pKa & relative strength of acid

Organic acid (blue) Those that lose a proton from O – H: methanol and acetic acid Those that lose a proton from C – H, a carbon atom next to a C=O double bond (O=C – C – H)

Organic bases (red) Have an atom with a lone pair of electrons that can bond to H + -O & -N

Lewis definition Accepts & donates an electron pair

Lewis acids & bases Reactions

Lewis Acids The Lewis definition of acidity includes metal cations, such as Mg 2+ : They accept a pair of electrons when they form a bond to a base Group 3A elements, such as BF 3 and AlCl 3, are Lewis acids because they have unfilled valence orbitals and can accept electron pairs from Lewis bases Transition-metal compounds, such as TiCl 4, FeCl 3, ZnCl 2, and SnCl 4, are Lewis acids Organic compounds that undergo addition reactions with Lewis bases (discussed later) are called electrophiles and therefore Lewis Acids

Lewis Bases Most oxygen- and nitrogen-containing organic compounds are Lewis bases because they have lone pairs of electrons Some compounds can act as both acids and bases, depending on the reaction chemists.blogfa.com/post- 379.aspx