Beruflich Dokumente
Kultur Dokumente
Chemistry
1-1
Review of
Molecular
Structure
Chapter 1
1-2
Organic Chemistry
C is a small atom
1-3
1-4
1-5
2
1
1-6
Aufbau Principle:
Hunds Rule:
1-8
1-9
Gilbert N. Lewis
Valence shell:
Valence electrons:
2A
H.
Al :
.
.
C: N :
.
Si : . P:
: O:
.
.
:S :
.
:F :
.
: Cl :
8A
He :
: Ne :
: :
7A
Na. Mg:
B:
5A 6A
: :
Be :
4A
Li .
3A
: Ar :
1-11
Covalent Bonds
H-H
Lewis Structures
In neutral molecules
1-15
Multiple Bonding
Bonded atoms can share more than one pair of
electrons to form multiple bonds
Molecular oxygen (O2) has a double bond
between the oxygen atoms
+
gives
1-16
H-N-H
H
NH3 (8)
Ammonia
H-C C-H
C2H2 (10)
Acetylene
H
H-C-H
H
CH4 (8)
Methane
H
C O
H
CH2O (12)
Formaldehyde
H-Cl
HCl (8)
Hydrogen chloride
O
H
H2CO3 (24)
Carbonic acid
1-17
Electronegativity
Electronegativity:
Pauling scale
1-18
Difference in
Electronegativity
Between Bonded Atoms
Less than 0.5
0.5 to 1.9
Greater than 1.9
Type of Bond
Nonpolar covalent
Polar covalent
Ions form
1-19
Cl
1-20
H-C
H-N
H-O
H-S
0.3
1.3
1.5
0.7
Bond
Dipole
Bond (D)
C-F
C-Cl
C-Br
C-I
1.4
1.5
1.4
1.2
Bond
Dipole
Bond (D)
C-O
C=O
C-N
-C=N
0.7
2.3
0.2
3.5
1-21
1-22
Cl
F
O
F
Carbon dioxide
=0D
Boron trifluoride
=0D
C
Cl
Cl
Cl
Carbon tetrachloride
=0D
1-23
Water
= 1.85D
H
Ammonia
= 1.47D
direction
of dipole
moment
1-24
O
C
Formaldehyde
= 2.33 D
1-25
Formation of Ions
A rough guideline:
Na
Na
Formal Charge
Number of
= valence electrons
in the neutral,
unbonded atom
All
One half of
unshared + all shared
electrons
electrons
1-27
Formal Charge
(a) NH2
(b) HCO3
(c) CO3
+
(d) CH3 NH3
(e) HCOO
(f) CH3COO
2-
1-28
Boron trifluoride
:Cl
Al
:Cl :
:F :
:Cl :
: :
: :
:F
6 electrons in the
valence shells of boron
and aluminum
: F:
Aluminum chloride
1-29
1-30
Resonance
O
and
H3 C C
O
H3 C C
O
Ethanoate ion
(acetate ion)
1-31
Resonance
1-32
Resonance
O:
C
:O:-
Nitrite ion
(equivalent contributing
structures)
O:
CH3
:O :-
:N
O:
: O:-
O:
:N
:O:-
Acetate ion
(equivalent contributing
structures)
1-33
Resonance
1-34
Resonance
Resonance
1-36
Resonance
H
Greater contribution;
both carbon and oxygen have
complete valence shells
CH3 O
+
C
H
Lesser contribution;
carbon has only 6 electrons
in its valence shell
1-37
Resonance
+
O
H
Greater contribution
(8 covalent bonds)
CH3 O
+
C
H
Lesser contribution
(7 covalent bonds)
1-38
Resonance
Greater contribution
(no separation of
unlike charges)
:O: -
O:
CH3 -C-CH3
CH3 -C-CH3
Lesser contribution
(separation of unlike
charges)
1-39
Resonance
C
H3 C
O
CH3
(a)
Lesser
contribution
(2)
C
H3 C
CH3
(b)
Greater
contribution
C
H3 C
CH3
(c)
Should not
be drawn
1-40
Structural Formulas
Types include
or
(CH3)2CH2
CH3CH(CH3)CH3
(CH3)3CH
1-42
1-43
CH3CH2OH
CH3CH2NHCH3
CH3CHClCH3
CH3CH=CHCH3
1-44
Line-Angle structures
1-45
*
*
(C14H30)
OK`
Trivalent carbon
1-47
E
1-48
_
3 from the bonds, must have a nonbonded lone pair (note that it has an
octet even!)
1-49
Acids
and
Bases
1-50
H3 O+(aq)
Hydronium ion
1-51
Brnsted-Lowry Definitions
: :
+
H O H + :O
+ H O
H
Proton
donor
Proton
acceptor
H
Proton
donor
H O:
H
Proton
acceptor
H
+
H O H + :N
H
+
+ H N H
H
1-52
H2O(l)
Water
(base)
Cl-(aq)
+ H3 O (aq)
Chloride
Hydronium
ion
ion
(conjugate
(conjugate
base of HCl) acid of H2O)
1-53
(base)
CH3 COO- +
NH4 +
Acetate
Ammonium
ion
ion
(conjugate base (conjugate acid
acetic acid)
of ammonia)
1-54
H
+
:N H
H
Acetic acid
Ammonia
(proton donor) (proton acceptor)
: O:
H
CH3 -C-O: + H-N-H
H
Acetate ion Ammonium
ion
: :
: O:
CH3 -C-O H
1-55
O
CH3 -C-O-H + H2 SO4
acetic acid
+ H
O
+
CH3 -C-O-H or
CH3 -C-O-H + HSO4
H
A
B
(protonation
(protonation
on the
on the
carbonyl oxygen) hydroxyl oxygen)
1-56
H
O
+
CH3-C-O-H
-C
A-1
(C and O have
complete octets)
A-2
(C has incomplete
octet)
H
O
+
CH3 -C=O-H
A-3
(C and O have
complete octets)
+
CH3 -C-O-H
H
B-1
+
CH3 -C-O-H
+
H
B-2
(charge separation and
adjacent positive charges)
+ H
O
CH3 -C-N-H or
H
A
(protonation
on the
amide oxygen)
OH
+
CH3-C-N-H + Cl
H
B
(protonation
on the
amide nitrogen)
1-59
CH3CO
Acetate
ion
+ H3O
Hydronium
ion
1-60
HA + H2 O
Keq =
[H3 O ][A ]
[HA][H2 O]
[H3 O+][A-]
[HA]
1-61
Acid
Weaker Ethane
acid
Ethylene
Ammonia
Hydrogen
Acetylene
Ethanol
Water
CH2 =CH2
NH3
H2
HC CH
CH3CH2OH
H2 O
pKa
Formula
CH3CH3
HCO3
C6H5 OH
+
NH4
H2 S
H2 CO3
CH3COOH
C6H5 COOH
H3 PO4
+
H3 O
H2 SO4
HCl
HBr
HI
51
44
38
35
25
15.9
15.7
10.64
10.33
9.95
9.24
7.04
6.36
4.76
4.19
2.1
-1.74
-5.2
-7
-8
-9
Conjugate Base
CH3CH2
Stronger
- conjugate
CH2 =CH
base
NH2
H
HC C
CH3CH2O
HO
CH3NH2
2-
CO3
C6H5 O
NH3
HS
HCO3
CH3COO
C6H5 COO
H2 PO4
H2 O
HSO4
Cl
Weaker
Br
conjugate
base
I
1-62
Acid-Base Equilibria
NH3
Acetic acid
Ammonia
(stronger base)
pKa 4.76
(stronger acid)
CH3 COO
NH4 +
1-63
Acid-Base Equilibria
HCO3CH3COH +
Acetic acid
Bicarbonate ion
pKa 4.76
(stronger acid)
CH3CO +
H2 CO3
Acetate ion Carbonic acid
pKa 6.36
(weaker acid)
1-64
:B
Lewis
base
+
A B
1-65
H :Br :
H H
sec-Butyl cation
(a carbocation)
CH3 CH 2
: :
+
CH3 -C C-CH3
:Br : Bromide
ion
F
B F
CH3 -C
C-CH3
H H
2-Bromobutane
CH3 CH 2
F
+
:O:
+
:O B-F
CH3 CH 2
F
F
CH3 CH 2
Diethyl ether Boron trifluoride A BF3-ether complex
(a Lewis base) (a Lewis acid)
1-66
pKa(NH4+) = 9
1-67