Chapter 1

organic chemistry : chemistry oI carbon compounds

biomass
coal
structure determination enormous carbon compounds
large size
complex by various arangement oI atoms
reactions
reaction mechanism
synthesis
dye, drug, paper, ink, paints, plastics
gasoline, rubber, Iood, clothing
technology
biology
medicine
organic compounds
petroleum

structural theory
ionic bond : electron transter ex) LiE p4
covalent bond : electron sharing ex) H

p5
quantum mechanics atomic orbital : probablity, electron density
Eig 1.1 & 1.2 electronic conIiguration
( Pauli exclusion principle )
Table 1.1
molecule
molecular orbital
atom

atom
Ior simplicity, localized molecular orbital ( bond orbital ) is used.
atomic orbital overlap bond orbital ex) H

( Eig 1.3 )
E

( Eig 1.4 )
bond
bond length
bond strength

H
2
;
H 1s
1
H H H H H H
covalent bond ( 2electrons
bond with opposite
spins)
E
2
;
E 1s
1
2s
2
2p
x
2
2p
y
2
2p
z
1
E E E E E E
BeCl
2
;
Be 1s
1
2s
2
1s
1
2s
2
2p
1
sp sp
( sp hybridization)
linear digonal
Cl Be Cl
BE
3
;
B 1s
1
2s
2
2p
1
1s
1
2s
2
2p
1
2p
1
sp
2
sp
2
sp
2
( sp
2
hybrization )
trigonal
B
E
E
E
CH
4
;
C 1s
1
2s
2
2p
1
2p
1
1s
1
2s
2
2p
1
2p
1
2p
1
sp
3
sp
3
sp
3
sp
3
( sp
3
hybrization )
tetrahedral
C H
H
H
H
109.5
o
NH

, H

O ; sp

hydridization
A : B
A : B
A B Homolysis

A B Heterolysis

bond dissociation energy ( D )

cf ) bond energy
in gas phase
N
H
H
H

N
H
H
H

6Kcal/mole
inversion occurs
no inversion in CH

in ionizing solvents


Certain covalent bonds have polarity dipole ( moment )
due to electronegativity CH

, CCl

; 0
NH

; 1.46 D
NE

; 0.24 D
Intermolecular Iorce
Ior non-ionic compd
dipole-dipole interaction hydrogen bonding
( N, O, E ) ~5 Kcal/mole
van der Waals Iorce Irom indyced dipole
the larger size, the stronger
Iorce
m.p. & b.p. depend on them
Eor dissolution , energy is required to break intermolecular Iorces
it is supplied by the bond Iormation between solute and
solvent molecules
CCl

, CH

( nonpolar ) not soluble in H

O
CH

OH ( polar ) soluble in H

O
R OH solubility in H

O depends on R
nonpolar polar
hydrophobic hydrophilic
lipophilic

ionic compds dissolved in a polar solvent
cation - neagtive end oI the solvent molecule
anion - positive end oI the solvent molecule
ion - dipole attraction
solvated
( hydrated )
aggregates supply
enough energy
weaker than interionic bond
Lowry-Brr nsted & Lewis electronegativity
H CH

H E
H OH
H Cl
H SH H SeH
H Br H I
H NH

H OH H E
H SH H Cl

oxonium ion
(p34)
Isomerism
complex
(p34)
size
charge