CHM-235 Organic Chemistry I
Course Description: Rigorous introduction to the
chemistry of carbon-containing compounds. Reaction mechanisms and recent
methods of synthesis emphasized.
Prerequisites: CHM152 and CHM152LL; or CHM154 and
CHM154LL.
Course Materials:
Here is a link for molecular model kits.
http://www.indigo.com/models/gphmodel/foundation-molecular-model-set-68845NV.html
This kit has orbital paddles.
www.darlingmodels.com
There are a few different
versions of the Molecular Visions Organic Set (Kit 1, 1A, or 2A).
These sets are cheaper (~$14.00)
but do not have orbital paddles.
As with all purchases, shop around. If you find another good website, let
me know.
Announcements
Change of venue for
my Tuesday office hours: I will have my
Tuesday 5:30-6:30pm office hours
in PS-149 as a review session for CHM 235 –
this is open to anyone in CHM 235 or anyone who
wants a refresher for
CHM 235 material.
More problem sets:
(from the Smith text).
A couple of extra
sets of problems for substitution and elimination:
Problem Sets (from Smith
text)
Chapter
1
Review on atoms and electrons: 1, 2
Bonds:
3, 4, 30, 31, 36, 68
Structures: 5, 6
Hybridization: 17, 18, 19, 26, 27, 28, 29, 63, 64, 65, 66,
67
Electronegativity: 32, 33, 34, 73, 74, 75
Charges:
7, 8, 37, 38, 39
Other problems: 35, 76, 77, 78, 79, 80
Resonance:
10, 11, 12, 13, 14, 15, 45, 46, 47, 49, 50, 52, 53, 82
Structures: 9, 16, 20, 21, 22, 23, 24, 25, 40, 41, 42,
54, 55, 56, 57, 58, 59, 60, 61
Chapter
2
Acid/base definitions: 1, 3, 23, 24, 25, 49, 50
Reactions of acids and bases: 5, 6, 11, 12, 16, 27, 30, 31, 32, 51, 52
Relative acidity: 7, 9, 10, 13, 14, 15, 19, 20, 22, 38, 44
Conjugate acids/bases: 28, 29
Chapter
3
Functional groups: 1, 2, 3, 15
Intermolecular forces: 4, 5, 6, 9, 10, 11, 12, 17, 18, 19, 20, 21,
22, 23, 26, 27, 28, 30, 33, 34, 35, 36
Isomers:
16
Other problems: 41, 42
More problems: 6, 7, 24, 29, 32
Chapter
4
Alkane
structure: 1, 2
Isomers:
5, 6, 8, 39, 59, 60
Nomenclature: 11, 12, 13, 14, 40, 41, 42, 43
Types of C and H: 3, 4, 7, 37, 38
Conformational analysis: 21, 22, 23, 24, 25, 44, 47, 48, 49, 50, 53
Newman projections: 20, 51, 52
Nomenclature: 39
Substituted cycloalkanes: 15, 16, 17, 29, 30, 31, 32, 54, 55, 58, 70
More problems: 18, 19, 26, 27, 28, 45, 46, 56, 57, 61
Chapter
5
Isomers:
1, 2, 16, 17
Chirality: 3, 4, 5, 6, 7, 8, 9, 10, 11
Nomenclature: 12, 13, 14, 15, 41, 42, 43, 44, 45
Enantiomers/diastereomers: 18,
19, 20, 21, 22, 23, 24, 25, 39
More isomers: 26,33, 34, 35, 36,
37, 38, 40, 46, 47
Other problems: 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58,
59, 62, 64
Chapter
6
Reaction types: 1, 23
Predicting products: 2, 24
Mechanisms: 3, 25, 26, 30, 42
Thermodynamics: 7, 8, 9, 10, 11, 12, 13, 35
Transition states: 14, 15, 38
Other problems: 51
Chapter
7
Types of halides: 1, 2, 43
Nomenclature: 3, 4, 41, 42, 44
Substitution reactions: 8, 9, 46, 47
Nucleophiles and
leaving groups: 10, 11, 12, 13, 17, 48,
49, 50, 51, 52, 53
Sn2:
18, 19, 20, 21, 22, 23, 55, 56, 57, 58, 69
Solvent:
14, 54, 71
Sn1:
25, 26, 27, 28, 29, 30, 59, 60, 61, 62, 63, 64
Sn1 vs. Sn2: 31, 32, 33, 35, 36, 37
Syntheses:
39, 40, 73, 75
Mechanisms: 54, 65, 67, 68, 70
More problems: 38, 74
Chapter
8
Predicting products: 1, 19, 23, 25, 26, 49, 51
Alkene classification: 2, 3, 4, 5, 6, 27, 28, 29, 30, 31
Mechanisms: 7, 8, 13, 17, 18, 24, 52, 53, 55
E2:
9, 10, 12, 20, 33, 34, 37, 38, 39, 44, 45
E1:
14, 40
E1 vs. Sn1: 16
E1 vs. E2:
21, 41, 42, 43
Other problems: 54, 56, 57, 58
Chapter
9
Structures: 1
Nomenclature: 2, 3, 4, 5, 38, 39, 40, 41
Physical properties: 6, 7, 8, 42
Preparation: 11, 12
Reactions:
13, 14, 15, 18, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 43, 44,
45, 46, 47, 48, 49, 53, 58, 61
Mechanisms: 16, 17, 19, 20, 33, 34, 50, 52, 54, 55, 56,
57, 62
Syntheses:
51, 59, 60
http://www.molsci.ucla.edu/pub/explorations.html
Problem Sets (from McMurry text, Spring 2008)
Chapter 1
Electron configuration: 1, 2, 21, 22, 27, 45
Hybridization: 10, 11, 13, 14, 15, 16, 24, 25, 30, 31,
32, 39, 40, 41, 43, 44, 46, 47, 48
Formulas: 5, 7, 23, 28, 34
Structures: 18, 19, 20, 27, 29, 33, 36, 37, 38, 49, 50, 51, 52
Drawing: 3, 4, 8, 9, 12, 17, 18, 19
More structures: 6, 26, 28, 35
Chapter 2
Bond polarity: 1, 2, 3, 4, 29, 30
Overall polarity: 5, 6, 31, 32, 33, 34, 26, 60
Charges: 8, 9, 35, 44
Resonance: 10, 36, 37, 38, 56, 57, 61
Acidity: 11, 12, 14, 15, 17, 18, 39, 40, 41, 42, 43, 45
More acid/base problems: 13, 46, 47, 48, 49, 55
Structures: 20, 21, 22, 23, 24, 25, 27, 28
Chapter 3
Functional Groups: 1, 2, 3, 21, 29, 30, 35, 24
Isomers: 4, 5, 6, 7, 25, 26, 27, 28, 31, 42
Nomenclature: 11, 12 13, 14, 39, 45, 46, 47, 39
Structures: 36, 37, 38, 61
Types of C and H: 8, 9, 10, 32, 40, 41, 44
Haloalkanes: 33, 34
Cycloalkanes: 15, 16, 17, 18, 19, 20, 23, 43, 50, 51
More nomenclature: 22, 48, 49
Isomers: 52, 53, 54, 55, 59, 60
Other problems: 56, 57, 58
Chapter 4
Conformations: 1, 2, 3, 4, 5, 24, 25, 26, 27, 28, 29, 30
Ring strain: 6, 7, 8, 9, 10
Cyclohexane chairs: 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 31, 32, 33, 34, 35, 36, 37, 38
Biomolecules, 39, 40
Cyclohexane boats: 19
Chapter 5
Reaction type: 1, 24
Nucleophiles and electrophiles: 4, 5, 20
Mechanisms: 6, 7, 8, 9, 18, 19, 26, 39, 40, 41, 42, 44, 47, 50
Thermodynamics: 10, 11
Energy diagrams: 16, 17, 21, 22, 27, 28, 29, 30
Functional groups: 23
Other questions: 25, 48, 49
Chapter 6
Nomenclature: 4, 5, 6, 20, 26, 27, 28, 29, 30, 31, 32, 41. 43
Isomerism: 7, 8, 9, 10, 11, 12, 21, 42, 44, 45
Alkene stability: 13, 33, 34, 35
Addition of hydrogen halides: 14, 15, 16, 17, 18, 39, 40
Mechanisms: 19, 48, 49, 50, 52
Carbocations: 22, 47, 53
Alkene structure: 37
Other reactions: 56, 57
Chapter 7
Addition of halogens: 3, 4, 54
Addition of water: 7, 8, 9, 10, 11, 21, 22, 27, 41, 48, 55, 56
Hydrogenation: 13
Polymerization: 17, 18, 46, 47
Halohydrin formation: 49
Reactions: 23, 24, 25, 26, 50, 58
Addition of acids: 35
Carbenes: 12, 42, 51
Oxidation: 14, 15, 16, 20, 28, 30, 33
Other problems: 29, 31, 32, 34, 36, 38, 40, 43, 44, 45, 52
Mechanisms: 37
Elimination reactions: 1, 2
Chapter 8
Nomenclature: 1, 2, 19, 20, 21, 40
Addition reactions: 3, 4, 5, 6, 7, 8, 22, 23
Oxidation: 9, 31
Acidity: 10
Syntheses: 11, 12, 13, 14, 30, 32, 33, 34, 35, 36, 37
Structures: 18, 47
Reactions: 24, 25, 26, 27, 28, 29, 41, 42, 43
Chapter 9
Chirality: 1, 2, 3, 4, 32, 33, 34, 35, 36, 37, 38, 43, 44, 45, 46, 47, 48, 49, 51, 52, 54, 55, 56, 57, 74
Nomenclature: 6, 7, 8, 9, 10, 28, 30
Diastereomers: 11, 12, 13
Meso compounds: 14, 15, 16, 29, 53
Stereoisomers: 17, 19, 27, 39, 40, 41, 42, 50
Reactions: 61, 62
Chapter 10
Nomenclature: 1, 2, 14, 17, 18
Radical Halogenation: 3, 5, 7, 15, 19, 24, 25, 32
Chapter 11
Sn2 inversion: 1, 2, 3, 23
Sn2 reactions: 4, 7, 26, 30, 36, 37, 38, 39, 40, 41, 51
Nucleophiles:
5, 32
Leaving Groups: 6
Sn1 reactions: 8, 10, 11, 12, 13, 35
Reactions: 14, 31, 43, 44
Mechanisms: 54, 55,
62, 69
Eliminations: 15, 16
E2: 17, 18, 19, 45, 49, 65
E1: 46
Reactions: 20, 25, 33, 50
Syntheses: 29, 34, 42, 64
Chapter 12
Mass spectra: 5, 25, 29, 30
IR: 6, 7, 10, 11, 12, 13, 14, 15,
34, 35, 37, 38, 39, 40, 41, 42, 43, 45
Interpreting spectra: 48, 49, 52,
53
Chapter 13
H1 NMR
(# of signals): 3, 14, 15, 31, 37
H1
NMR (chemical shift): 16, 17
H1
NMR (integrations): 18, 39
H1
NMR (splitting): 19, 20, 21, 24, 40, 41,
42, 43
C13
NMR: 6, 7, 8, 12, 25, 32, 34, 45
Structure determination: 23, 26,
27, 44, 46, 47, 48, 49, 50, 51, 52, 53, 55, 56, 57, 58, 66, 67
Chapter 14
Diene electrophilic
additions: 2, 3, 4, 17, 22, 27
Diels-Alder reaction: 7, 8, 9,
10, 18, 19, 28, 33, 34, 36, 40, 44
UV-visible spectroscopy: 16, 20,
23, 24, 31, 32, 46, 48, 49
Links:
Hybrid Orbitals
A couple of key points to remember:
1 - If you add n atomic orbitals,
you'll end up with n hybrid orbitals.
2 - The hybrid orbitals formed
will point as far apart as possible.
3 - Remember that in the case of sp2 and sp
hybrids there are unhybridized p-orbitals
remaining.
For some alternate depictions of atomic orbitals, there are a many well-constructed websites.
Below are a few URL's you can check out. I tried to stick to the
less elaborate sites so that they could run on most computers.
Electron
Motion Why worry about orbitals and electron motion in the first place.
http://micro.magnet.fsu.edu/electromag/java/atomicorbitals/
This site shows images of s, p , d, and
f atomic orbitals. You can view them
individually or several at a time. Keep in mind that we will deal mainly
with hybridization of just the s and p atomic orbitals.
Take a look at the f-orbitals just for fun.
http://www.orbitals.com/orb
This website has images of various atomic orbitals,
but not just s, p , d, and f orbitals.
It even shows images of more complicated orbitals.
http://www.towson.edu/~ladon/carbon.html
This is a tutorial on the electron configurations in carbon atoms and it also
deals with hybridized orbitals.
Some more interesting links:
http://science.nasa.gov/Realtime/jtrack/3d/JTrack3d.html
Choose
your favorite satellite and see where it is. This site shows the current
location of
hundreds of
satellites in orbit around Earth.
http://www.lehsd.k12.nj.us/Pinelands/slideshow/sld001.htm
Read about my home
state -
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