Chemistry 2100
Fall 2011
Bloom’s Taxonomy
Richard C. Overbaugh, Lynn SchultzOld 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
VIIAVIAVA IVAIIIA
IIBIBVIIBVIBVBIVBIIIBMg
24.31
12
O16.00
8Ne20.18
10F19.00
9N14.01
7B10.81
5Be9.012
4Li6.941
3
He4.003
2
IA
1
2
3
4
5
6
7
IIA
VIIIA
VIIIB Na22.99
11
H1.008
1
Al26.98
13Si28.09
14P30.97
15S32.07
16Cl35.45
17Ar39.95
18
K39.10
19 20
40.08Ca
21
44.96Sc
22
47.88Ti V
50.94
23 24
52.00Cr
25
54.94Mn
26
55.85Fe
27
58.93Co
28
58.69Ni
29
63.55Cu
30
65.38Zn
31
69.72Ga
32
72.59Ge
33
74.92As
34
78.96Se
35
79.90Br
36
83.80Kr
37
85.47Rb
38
87.62Sr Y
88.91
39 40
91.22Zr
41
92.91Nb
42
95.94Mo
43
(98)Tc
44
101.1Ru
45
102.9Rh
46
106.4Pd
47
107.9Ag
48
112.4Cd
49
114.8In
50
118.7Sn
51
121.8Sb
52
127.6Te I
126.9
53 54
131.3Xe
55
132.9Cs
56
137.3Ba
57
138.9La
58
140.1Ce
59
140.9Pr
60
144.2Nd
61
(145)Pm
62
150.4Sm
63
152.0Eu
64
157.3Gd
65
158.9Tb
66
162.5Dy
67
164.9Ho
68
167.3Er
69
168.9Tm
70
173.0Yb
71
175.0Lu
72
178.5Hf
73
180.9Ta W
183.9
74 75
186.2Re
76
190.2Os
77
192.2Ir
78
195.1Pt
79
197.0Au
80
200.6Hg
81
204.4Tl
82
207.2Pb
83
209.0Bi
84
(209)Po
85
(210)At
86
(222)Rn
87
(223)Fr
88
(226)Ra
89
(227)Ac
104
(261)Rf
105
(262)Db
106
(263)Sg
107
(262)Bh
108
(265)Hs
109
(266)Mt
110
(269)Uun
111
(272)Uuu
112
(277)Uub
114
(289)Uuq
116
(289)Uuh
118
(293)Uuo
90
232.0Th
91
(231)Pa U
238.0
92 93
(238)Np
94
(244)Pu
95
(243)Am
96
(247)Cm
97
(247)Bk
98
(251)Cf
99
(252)Es
100
(257)Fm
101
(258)Md
102
(259)No
103
(260)Lw
C6
12.01
C
General Chemistry
H 1 0
C 4 0
N 3 1
O 2 2
X 1 3
element covalent bonds lone pairs
~109.5°
H
CH
H
H
x
x
x
C HxH
H
H
Valence Shell Electron Pair Repulsion Theory
4 tetrahedral 109.5°
3 trigonal planar 120°
2 linear 180°
regions of predicted predicted electron density geometry bond angles
~109.5°
• •
C N
H
HH
H
H
CC
H
HH
H
120° C CH H
180°
NC
HH
H••
120°
Meet the Elements
http://www.youtube.com/watch?v=Uy0m7jnyv6U
English LanguageCursive
Shorthand
Type
The language of Chemistry
O HC
H
C
H
H
H
H OH
Molecular Formula
C2H6O
Structural Formula
Condensed Structural Formula
CH3CH2OH
3D Structural Formula
Molecular Representation
Skeletal, line-angle Formula
O H
H
H
H
H
H
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-C-HH
HH-C-C-H
H
H
H
H
Methane Ethane
Propane & Butane
C
H
H
H
C
H
H
C
H
H
H
CH3CH2CH2CH3CH3CH2CH3 CH3CH2CH2CH2CH3CH3CH2CH2CH3CH3CH2CH3 CH3CH2CH2CH2CH3PentaneButanePropane PentaneButanePropane
Condensedstructural
formula
Line-angleformula
Ball-and-stick model
C
H
H
H
C
H
H
C
H
H
C
H
H
H
Butane & Constitutional Isomers
C
H
H
H
C
H
H
C
H
H
C
H
H
H
CH3CH2CH2CH3 CH3CHCH3
CH3
Butane(bp -0.5°C)
2-Methylpropane(bp -11.6°C)
C
H
H
HC
C
H H
H
H
C
H
H
H
n-butaneisobutane
C4H10
How many constitutional isomers?
C5H12 3
C6H14 5
C10H22 75
C20H42 366,319
C30H62 > 4 billion
C40H82 > 65 trillion
C20H42 366,319
C30H62 > 4 billion
C40H82 > 65 trillion
constitutional (structural) isomers
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
C3 "prop" Gr., protos pion (first fat)*
C4 "but" L., butyrum (butter)C5 "pent" Gr., pente (five)
C6 "hex" Gr., hex (six)
C7 "hept" Gr., hepta (seven)C8 "oct" L., octo (eight)C9 "non" L., nona (nine)C10 "dec" L., deca (ten)
C1 "meth" Gr., methy (wine)*
C2 "eth" Gr., aithein (blaze)
Alkyl groups
-CH2CH3
-CH3
-CH2CH2CH3
-CHCH3CH3
-CH2CH2CH2CH3
-CH2CHCH3CH3
-CHCH2CH3CH3
-CCH3
CH3
CH3
tert-butyl
sec-butyl
isobutyl
butyl
isopropyl
propyl
ethyl
methylName
CondensedStructural Formula
CondensedStructural FormulaName
Naming Algorithm
(a) parent C-chain
(b) substituents
(c) numbers
(d) alphabetical listing
Parent
—Suffix
IUPAC Rules
Substituents—
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
CH4CH3CH3CH3CH2CH3CH3(CH2)2CH3
CH3(CH2)3CH3
CH3(CH2)4CH3
CH3(CH2)5CH3
CH3(CH2)6CH3CH3(CH2)7CH3
CH3(CH2)8CH3
methane
ethanepropane
butane
pentane
hexane
heptane
octanenonane
decane
Name
CondensedStructrualFormula
mp(°C)
bp(°C)
-182
-183
-190-138
-130
-95
-90
-57-51
-30
-164
-88
-420
36
69
98
126151
174
(a gas)
(a gas)
(a gas)(a gas)
0.626
0.659
0.684
0.7030.718
0.730
*For comparison, the density of H2O is 1 g/mL at 4°C.
Mol wt(amu)
16.0
30.144.1
58.1
72.2
86.2
100.2
114.2128.3142.3
Density of Liquid
(g/mL at 0° C)*
Isomers and Physical Properties
pentanebp 36°C; mp -130°C
d 0.626 neopentanebp 9°C; mp -16°C
d 0.606
CH3 CH2 CH2 CH2 CH3
CH3 C CH3
CH3
CH3 CH3 CH
CH3
CH2 CH3
isopentanebp 28°C; mp -160°C
d 0.620
Alkane Origins
Gasoline, Combustion, & Octane Ratings
OH
C6-C12 mixture
CH4 + 2O2 CO2 + 2H2O + 212 kcal/mol
CH3CH2CH3 + 5 O2 3 CO2 + 4H2O + 530 kcal/mol
but…
2 CH3CH2CH3 + 7 O2 2 CO2 + 2 CO + 2 C + 8H2O + < 530 kcal/mol
Octane Rating – Controlled Explosions
2,2,4-trimethylpentane(iso-octane)Octane rating 100
HeptaneOctane rating 0
EthanolOctane rating 105
OctaneOctane Rating -20
Halogenation
n
F F
F F
F F
F F
Perfluorodecalin
polytetrafluoroethylene (PTFE) Teflon
Cl Cl
F F
dichlorodifluoromethaneFreon
dichlorodiphenyltrichloroethaneDDT
CycloalkanesCnH2n
60° 90° 108° 120° 128° 135°
60° 88° 105° 109° 109° 109°
Interesting Cycloalkane Derivatives
Testosterone
Cholesterol
Estradiol
Muskone
Cyclohexane
Cyclohexane – the Chair C
C
CC
C
C
1
2
3
5
6
4
"chair"
Cyclohexane Substituents H
H
CH3
CH3
H
H
H
H
1
6 5
4
3 (3)
(3')(1)
2
3
2
1
65
4
(3)
(3')
(1)
95% 5%1,3-diaxial interactions
H
H
CH3
CH3
H
H
H
H
1
6 5
4
3 (3)
(3')(1)
2
3
2
1
65
4
(3)
(3')
(1)
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Constitutional
IsomersStereoisomers
ConformationalIsomers
GeometricIsomers
Enantiomers Diastereomers
single bond rotation
chiral achiral
sameconnections
differentconnections
notmirrorimages
mirrorimages
Isomers
Geometric Isomers, a.k.a.cis-trans isomers
perspectiveHaworth
Cl
Cl
ClClH
H HH
cis-1,2-dichlorocyclopentane
perspective
HaworthCl
H
ClHH
Cl HCl
trans-1,2-dichlorocyclopentane
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