Chemistry 2100
Fall 2011
Bloom’s Taxonomy
Richard C. Overbaugh, Lynn Schultz
Old Dominion University
Student Objectives for this course
• Analyze and explain chemical differences among the various
classes of organic compounds
• Evaluate carbohydrate structure and reactivity
• Compare and contrast the four main classes of key
biomolecules
• Explain the processes of protein folding and enzymatic
catalysis
• Use knowledge of replication, transcription, and translation to
predict the outcome of genetic diseases
• Relate biochemical concepts to digestion, metabolism, and
nutrition
Organic & Biological Chemistry
6
C
12 .01
IA
1
2
3
4
5
6
7
1
2
H
I IA
1 .0 0 8
3
Li
6 .9 4 1
11
4
I II A I VA
5
Be
9 .0 1 2
12
19
K
3 9. 1 0
37
Rb
8 5. 4 7
55
Cs
1 32 . 9
87
Fr
(2 2 3 )
I II B
2 4. 3 1
20
Ca
21
Sc
4 0. 0 8
38
Sr
4 4. 9 6
39
8 7. 6 2
56
Ba
1 37 . 3
88
Ra
(2 2 6 )
B
Y
8 8. 9 1
57
La
1 38 . 9
89
Ac
(2 2 7 )
I VB
22
Ti
4 7. 8 8
40
Zr
9 1. 2 2
72
Hf
1 78 . 5
1 04
Rf
(2 6 1 )
VB
23
V
5 0. 9 4
41
Nb
9 2. 9 1
73
Ta
1 80 . 9
1 05
Db
(2 6 2 )
58
Ce
1 40 . 1
90
Th
2 32 . 0
VI B
24
Cr
5 2. 0 0
42
VI I B
25
Mn
5 4. 9 4
43
Mo Tc
9 5. 9 4
74
W
1 83 . 9
1 06
Sg
(2 6 3 )
59
Pr
1 40 . 9
91
Pa
(2 3 1 )
(9 8 )
75
Re
1 86 . 2
1 07
Bh
(2 6 2 )
60
Nd
1 44 . 2
92
U
2 38 . 0
13
VI I IB
26
Fe
5 5. 8 5
44
Ru
1 01 . 1
76
Os
1 90 . 2
1 08
Hs
(2 6 5 )
61
Pm
(1 4 5 )
93
Np
(2 3 8 )
27
Co
5 8. 9 3
45
Rh
1 02 . 9
77
Ir
1 92 . 2
1 09
IB
28
Ni
5 8. 6 9
46
Pd
1 06 . 4
78
Pt
1 95 . 1
1 10
29
Cu
6 3. 5 5
47
Ag
1 07 . 9
79
Au
1 97 . 0
1 11
I IB
30
Zn
6 5. 3 8
48
Cd
1 12 . 4
80
Hg
2 00 . 6
Al
2 6. 9 8
31
Ga
6 9. 7 2
49
In
1 14 . 8
81
Tl
2 04 . 4
1 12
62
Sm
1 50 . 4
94
Pu
(2 4 4 )
(2 6 9 )
63
Eu
1 52 . 0
95
(2 7 2 )
64
Gd
1 57 . 3
96
Tb
1 58 . 9
97
Am Cm Bk
(2 4 3 )
(2 4 7 )
(2 4 7 )
1 4. 0 1
14
Si
2 8. 0 9
32
Ge
7 2. 5 9
50
Sn
1 18 . 7
82
Pb
2 07 . 2
15
P
3 0. 9 7
33
As
7 4. 9 2
51
Sb
1 21 . 8
83
Bi
2 09 . 0
Dy
1 62 . 5
98
Cf
(2 5 1 )
67
Ho
1 64 . 9
99
Es
(2 5 2 )
8
O
1 6. 0 0
16
S
3 2. 0 7
34
Se
7 8. 9 6
52
Te
1 27 . 6
84
Po
(2 0 9 )
9
F
1 9. 0 0
17
Cl
3 5. 4 5
35
Br
7 9. 9 0
53
I
1 26 . 9
85
At
(2 1 0 )
Er
1 67 . 3
1 00
Fm
(2 5 7 )
69
Tm
1 68 . 9
1 01
Ne
2 0. 1 8
18
Ar
3 9. 9 5
36
Kr
8 3. 8 0
54
Xe
1 31 . 3
86
Rn
(2 2 2 )
(2 9 3 )
70
Yb
1 73 . 0
1 02
Md No
(2 5 8 )
4 .0 0 3
10
Uu o
(2 8 9 )
68
He
1 18
Uu h
(2 8 9 )
66
VI A VI I A
1 16
Uu q
(2 7 7 )
65
N
1 14
Mt Uu n Uu u Uu b
(2 6 6 )
VA
7
1 0. 8 1
Na Mg
2 2. 9 9
VI I IA
(2 5 9 )
71
Lu
1 75 . 0
1 03
Lw
(2 6 0 )
General Chemistry
element
covalent bonds
lone pairs
H
1
0
C
4
0
N
3
1
O
2
2
X
1
3
H
H
x
Hx C
x
H
xH
H
H
C
H
~109.5°
Valence Shell Electron Pair
Repulsion Theory
regions of
electron density
predicted
geometry
predicted
bond angles
4
tetrahedral
109.5°
3
trigonal planar
120°
2
linear
180°
H
H
H
••
C
N
H
H
C
H
H
~109.5°
H
C
120°
H
H
C
H
••
N
120°
H
H C C H
180°
Meet the Elements
http://www.youtube.com/watch?v=Uy0m7jnyv6U
English Language
Cursive
Print
Shorthand
Type
The language of Chemistry
Molecular Formula
3D Structural Formula
C2H6O
Structural Formula
Skeletal, line-angle Formula
Condensed
Structural Formula
Molecular Representation
CH3CH2OH
or
Alkanes
• Simplest hydrocarbons
• Composed of only single bonds
• Often referred to as aliphatic hydrocarbons
– From Greek aleiphar (fat or oil)
• Also called Paraffins
– From Latin parum affinis (barely reactive)
• General formula: CnH2n+2
Methane & Ethane
H
H-C-H
H
Methane
HH
H-C-C-H
HH
Eth ane
Propane & Butane
Ball-andstick model
Line-an gle
formula
Conden sed
structural
formula
CH3 CH2 CH3
Propane
CH3 CH2 CH2 CH3
Butane
CH3 CH2 CH2 C
Pentan
Butane & Constitutional Isomers
CH3 CH2 CH2 CH3
Bu tane
(bp -0.5°C)
CH3
CH3 CHCH3
2-Methylp ropan e
(bp -11.6°C)
C4H10
n-butane
isobutane
How many constitutional isomers?
constitutional (structural) isomers
C20H42
366,319
C20H42
366,319
C30H62
> 4 billion
C5H12
3
C6H14
5
C30H62
C40H82
> 4 billion
> 65 trillion
C10H22
75
C40H82
> 65 trillion
Naming Conventions:
IUPAC Nomenclature
• International Union of Pure and Applied
Chemistry
• Gives a set of unambiguous names
• Despite this, common names are still used
Naming Alkanes
#C Prefix + -ane
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
"meth" Gr., methy (wine)*
"eth" Gr., aithein (blaze)
"prop" Gr., protos pion (first fat)*
"but" L., butyrum (butter)
"pent" Gr., pente (five)
"hex" Gr., hex (six)
"hept" Gr., hepta (seven)
"oct" L., octo (eight)
"non" L., nona (nine)
"dec" L., deca (ten)
Alkyl groups
Name
methyl
Con densed
Structu ral Formula
-CH3
ethyl
-CH2 CH3
propyl
-CH2 CH2 CH3
isopropyl -CHCH3
CH3
bu tyl
-CH2 CH2 CH2 CH3
Name
isobu tyl
sec-butyl
Con densed
Structural Formula
-CH2 CHCH3
CH3
-CHCH2 CH3
CH3
CH3
t ert-butyl -CCH3
CH3
Naming Algorithm
Substituents—Parent—Suffix
IUPAC Rules
(a) parent C-chain
(b) substituents
(c) numbers
(d) alphabetical listing
Dreadful Details!
• 1. The name for an alkane with an unbranched chain of
carbon atoms consists of a prefix showing the number
of carbon atoms and the ending -ane.
• 2. For branched-chain alkanes, the longest chain of
carbon atoms is the parent chain and its name is the
root name.
• 3. Name and number each substituent on the parent
chain and use a hyphen to connect the number to the
name.
• 4. If there is one substituent, number the parent chain
from the end that gives the substituent the lower
number.
Dreadful details (part 2)!
• 5. If the same substituent occurs more than once:
– Number the parent chain from the end that gives the lower number to
the substituent encountered first.
– Indicate the number of times the substituent occurs by a prefix di-, tri-,
tetra-, penta-, hexa-, and so forth.
– Use a comma to separate position numbers.
• 6. If there are two or more different substituents
– List them in alphabetical order.
– Number the chain from the end that gives the lower number to the
substituent encountered first.
– If there are different substituents at equivalent positions on opposite ends
of the parent chain, give the substituent of lower alphabetical order the
lower number.
• 7. Do not include the prefixes di-, tri-, tetra-, and so forth or the
hyphenated prefixes sec- and tert- in alphabetizing;
– Alphabetize the names of substituents first, and then insert these prefixes.
Alkane Origins
Physical Properties of Alkanes
Name
methan e
Conden sed
Stru ctrual
Formula
Mol w t
(amu)
16.0
butane
CH4
CH3 CH3
CH3 CH2 CH3
CH3 ( CH2 ) 2 CH3
pentane
eth ane
propan e
mp
(°C)
-182
D ensity
of Liquid
bp
(°C) (g/mL at 0° C)*
(a gas)
-164
-183
-88
(a gas)
58.1
-190
-138
-42
0
(a gas)
(a gas)
CH3 ( CH2 ) 3 CH3
72.2
-130
36
0.626
hexane
CH3 ( CH2 ) 4 CH3
86.2
-95
69
0.659
heptane
CH3 ( CH2 ) 5 CH3
100.2
-90
98
0.684
octan e
non ane
CH3 ( CH2 ) 6 CH3
CH3 ( CH2 ) 7 CH3
-57
-51
126
151
0.703
0.718
decane
CH3 ( CH2 ) 8 CH3
114.2
128.3
142.3
-30
174
0.730
30.1
44.1
*For comp aris on , th e dens ity of H2 O is 1 g/mL at 4°C.
Isomers and Physical Properties
CH3
CH 3
CH 2
CH 2
CH 2
CH 3
CH3
CH3
pentane
bp 36°C; mp -130°C
d 0.626
neopentane
bp 9°C; mp -16°C
d 0.606
CH3
CH3
C CH3
CH CH2
CH3
isopentane
bp 28°C; mp -160°C
d 0.620
Alkane Origins
Gasoline, Combustion,
& Octane Ratings
CH4 + 2O2  CO2 + 2H2O + 212 kcal/mol
CH3CH2CH3 + 5 O2  3 CO2 + 4H2O + 530 kcal/mol
but…
C6-C12 mixture
2 CH3CH2CH3 + 7 O2  2 CO2 + 2 CO + 2 C + 8H2O + < 530 kcal/mol
Octane Rating – Controlled Explosions
Ethanol
Octane rating 105
2,2,4-trimethylpentane
(iso-octane)
Octane rating 100
Heptane
Octane rating 0
Octane
Octane Rating -20
Halogenation
polytetrafluoroethylene (PTFE)
Teflon
dichlorodiphenyltrichloroethane
DDT
dichlorodifluoromethane
Freon
Perfluorodecalin
Cycloalkanes
CnH2n
60°
90°
108°
120°
128°
135°
60°
88°
105°
109°
109°
109°
Interesting Cycloalkane Derivatives
Testosterone
Cholesterol
Estradiol
Muskone
Cyclohexane
Cyclohexane – the Chair
6
C
1
C
C
5
C
2
"chair"
C
3
4
C
Cyclohexane Substituents
CH33
CH
H
H
H
H
H
H
44
22
CH33
CH
22
66
(3')
55 (3')
H
H
11
H
H
(3)
33 (3)
66
(1)
(1)
(1)
(1)
(3)
(3)
(3')
(3')
55
11
44
95%
H
H
33
1,3-diaxial interactions
5%
Geometric Isomers, a.k.a.
cis-trans isomers
H
H
H
Cl
Cl
perspective
Cl
H
H
Cl
H
Cl
Cl
Haworth
cis-1,2-dichlorocyclopentane
H
Cl
perspective
H
Cl
Haworth
trans-1,2-dichlorocyclopentane