organic chemistry fall, 2006 by 駱碧秀老師 time: tue. 08:10-10:00 & wed. 13:00-14:00...

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 5018

E-mail: blou@mail.cgu.edu.tw

Office Hours: Tuesday 10:10-12:00 am

Lecture & Assignment Schedule (NEW) Week Date 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 12/19,20 Carboxylic Acids & Derivatives (10)

15 12/26,27 Carbonyl Alpha-Substitution Reactions (11)16 01/02,03 Amines (12)17 01/08,09 Biomolecules: Proteins18 01/16 期末考 (30%)

Lecture & Assignment Schedule Week Date Topics

1 09/19,20 Introduction & 2 09/26,27 Structure & Bonding (1) 3 10/03,04 Alkanes (2) 4 10/10,11 Alkenes (3) 5 10/17,18 Reaction of Alkenes & Alkynes (4)6 10/24,25 Aromatic Compounds (5)

7 10/31,01 Stereochemistry (6) 8 11/07,08 Alkyl Halides (7) 9 11/14 期中考 10 11/21,22 Structure Determination (13) 11 11/28,29 Alcohols-1 (8)12 12/05,06 Alcohols-2 (8)13 12/12,13 Aldehydes & Ketones (9)14 12/19,20 Carboxylic Acids & Derivatives (10)

15 12/26,27 Carbonyl Alpha-Substitution Reactions (11)16 01/02,03 Amines (12)17 01/08,09 Biomolecules: Proteins18 01/16 期末考

Text Book

“Fundamentals of Organic Chemistry” 6th 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: (2x10-10 m)

Nucleus• Protons (+) 10-14 ~ 10-15 m• neutrons

Electrons (-) 10-10 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

Kekulé strutures (line-bond structure)

•Table 1.2

1.4 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) SP3 orbitals : Methane

Ethane:CH3-CH3

1.8 Double and Triple Bonds

Ethylene C2H4

bond P bond

Acetylene C2H2

One -bond & two -bonds

1.9 Bond Polarity & Electronegativity

Covalent bond to ionic bond

EN = 0 0< EN <2.0 EN>2.0

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 Mg2+ : They accept a pair of electrons when they form a bond to a base

Group 3A elements, such as BF3 and AlCl3, are Lewis acids because they have unfilled valence orbitals and can accept electron pairs from Lewis bases

Transition-metal compounds, such as TiCl4, FeCl3, ZnCl2, and SnCl4, 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 reactionhttp://tabriz-

chemists.blogfa.com/post-379.aspx