Organic Chemistry

A Brief Introduction
 References
 http://www.cem.msu.edu/~reusch/VirtualT
ext/intro1.htm#contnt
 http://www.askthenerd.com/ocol/
 Organic Chemistry, Francis A.Carey,
edition: 4th, Pub. Date: 2000,
Publisher(s): McGraw-Hill
 References
 《有机化学》郭书好主编，广州：广东科
技出版社 , 2004
 《有机化学网络课程》郭书好主编，高等
教育出版社， 2003,http:// 202.116.0.143/
yjhx/ index.htm
 《有机化学》（第二版） 胡宏纹主编 高
等教育出版社 1990
 Chapter 1

Structure of Organic
Compounds
 1.1 Inorganic and organic
Compounds
 In early time
 Inorganic compound: from mineral
sources
 Organic compounds: from plants or
animals
 The differences:“ vital force”
 Could not be synthesized in the lab
 1.1 Inorganic and organic
Compounds
 Organic compounds
 Main atoms:carbon and hydrogen
 Limited number of other elements: H,O,N-
hydrogen,oxygen,and nitrogen.
 1.2 Atomic Structure
 Atomic orbitals
 Designated by the letters s,p,d,f
 Differ in energy, shape, and orientation
 Consider the only s, p orbitals
 Nucleus is the center of s, p orbitals
 1.2 Atomic Structure
 s Orbital:spherical region of space-global
 p Orbital:like dumb bells
 2p orbital contain: three orbitals px ,py. pz
 x,y,z emphasize that they are mutally
perpendicular to one another.
 1.2 Atomic Structure
 Valence shell electrons
 The valence shell:outermost shell,higher
electrons location.
 Participate in chemical reaction
 Valence electrons:H-1e,C-4e,N-5e,O-6e
 Form bonds: H-1,C-4,N-3,O-2
 1.3 Types of Bonds
 Lewis octet rule
 Seond period atoms:such as C,O,N
 Form bonds by transferring or sharing
electrons
 Each atom surrounded by eight
electrons(ns2 + npx2 + npy2 + npz2).
 Highest energy shell:such as C,2s and 2p
 1.3 Types of Bonds
 Ionic bonds
 One or more electrons transfer among
atoms
 Negative ions are called anions: obtain
electron
 Positive ions are called cations: lost
electron
 1.3 Types of Bonds
 Lewis structure:valence electrons,dot
represent a electron
 Chloride is much more electronegativity
Na + Cl Na + Cl
 Covalent bonds
 Two atoms
 Mutal shareing pairs of electrons
 Forming condition
 1.3 Types of Bonds
 Too small different electronegativity
between two atoms
 Cann’t tranfer elctrons to form ion
 Bonding electrons
 Shared electrons
 Located in the space between the two nuclei
 Nonbonding electrons, lone pair electrons,
or unshared electron pairs
 Valence electrons
 1.3 Types of Bonds
 Electrons pair
 Not share with other atom
 Lewis structure
 Covalent bond: a dash line
 Nonbonding electrons:pairs of dots
located about the atomic symbols
H bonding electrons
H C Cl nonbonding pairs of electrons
H
chloromethane
 1.3 Types of Bonds
 4.Multiple covalent bonds
 Double bonds:two shared pairs of electrons
 Triple bonds:three shared pairs of electrons
 A carbon atom can form single,double,triple
bonds with other atoms.
single bond double bond triple bond
shareing 2 e- shareing 4 e- shareing 6 e

H H
H H
H C C H C C H C C H
H H H H
ethane ethylene acetylene
 1.3 Types of Bonds
 Polar covalent bonds
 Difference electronegativities
 For H—Cl, atom Cl:
 Higher electronegativity,partial negative charge
(show with δ-)
 For H—Cl, atom H:
 Lower electronegativity,partial positive charge
(show withδ+)
 Electronegativity :the power of electrons
attraction
 1.4 Orbitals and Molecular
Shapes
 Mixing of two or more orbitals in the bonded
atoms
 For carbon:2s mix with 2p
 Hybridized orbital:same energy,same
shape,contain one electron
 Differ only in the position in space
 Maximum separation of electron in the space
 Formσbond with H or C and other atoms
 sp3 Hybridization of carbon
 1.4 Orbitals and Molecular
Shapes
 One s + three p orbitals= four sp3 orbitals
 Extend to the corners of a tetrahydron
 Form four σ bonds
1.4 Orbitals and Molecular
Shapes
1.4 Orbitals and Molecular Shapes
 sp2 Hybridization of carbon
 A 2s + two 2p orbitals=three sp2 orbitals
 Extend to the corner of triangle
 Three hybridized orbitals form 3 σ bonds
 In ethylene,two with H,one with C
 Left p orbital form π bond with C
 Each p orbital is perpendicular to the plane
containing the sp2 orbitals
 The double bond contain one σ and π bonds
1.4 Orbitals and Molecular Shapes
1.4 Orbitals and Molecular Shapes
 1.4 Orbitals and Molecular
Shapes
sp hybridization of carbon
 A 2s + one 2p orbitals=two sp orbitals
 Extend to two end of a line
 Two hybridized orbitals form 2 σ bonds
 In acetylene,one with H,one with C
 Left 2 p orbitals form two π bonds with C
1.4 Orbitals and Molecular Shapes
 1.5 Structural Formulas
 Molecular formula----atomic composition
butane C4H10
 Structural formula----arrangement of atoms and
bonds
butane CH3―CH2―CH2―CH3
 Condensed structural formula----specific bonds
 Butane CH3CH2CH2CH3 or CH3(CH2)2CH3
 ―CH2― unit:methlene group
 1.5 Structural Formulas
 Bond-line structure
Br Br
CH3 CH2 CHBr CH3 is CH3 CH is
CH2 CH3
CH2 CH2
is
CH2 CH2

O O
CH2 CH2 C
is
CH CH2 CH3
 1.5 Structural Formulas
 Three-dimensional structures and models
 Perspective structure
H
dashed line:behind the paper
C H
H
H wedge line:infront the paper

 Ball-and-stick model
 Space-filling model
 1.6 Isomers
 Same molecular formula,different
structures
 Skeletal isomers:different carbon skeleton
CH3 CH2 CH2 CH3 CH3 CH CH3
CH3
butane isobutane
 Functional isomers:different functinal
group
CH3 CH2 OH CH3 O CH3
ethanol methyl ether
 1.6 Isomers
 Position isomers:same functional groups,
different position on the carbon skeleton

OH group is on OH group is in
the end of the chain. the middle of the chain.
OH
CH3 CH2 CH2 OH CH3 CH CH3
1-propanol 2-propanol