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Lecture01 s05
Lecture01 s05
Memorizing the structure, properties, and reactivities of each molecule will severely limit your abilities Organic chemistry is rational and systematic Goal: Learn tools to dissect and analyze organic chemistry that is unfamiliar
Study Tips
1. 2. 3. 4. 5. 6. Read the suggested readings before coming to class and record the main ideas. After each lecture, summarize the major ideas and concepts in your notes within 24 hours of class. Annotate these summaries from your study of the textbook Work the problems independently Master the material from each lecture before going to the next one. Spend a few minutes each day on review to prevent becoming overwhelmed on the night before an exam.
Syllabus
Organic chemistry Structure and reactivity Resonance Acidity and basicity of organic compounds Alkanes Stereochemistry Overview of organic reactions Alkenes Alkynes Alkyl halides Benzene and aromatic compounds Alcohols and phenols Carbonyl compounds Synthesis using the chemistry of 5.12
Background Review
1. 2. 3. 4. 5. Atomic Structure Atomic Orbitals Electron Configuration Ionic/Covalent Bonding Lewis Structures 6. Formal Charges 7. Valence Bond Theory 8. VSEPR Theory 9. Hybridization 10. MO Theory
Go the the 5.12 Web Page and work through: q Background Handout (PowerPoint and .pdf) q Background Knowledge Quiz
Suggested Readings (McMurry): 1.1-1.12, 2.1-2.3 Suggested Problems (McMurry): 1.1-1.16, 1.21-1.47, 2.1-2.9, 2.29-2.35
Lecture 1: Outline
q Organic Chemistry q Relationship of Structure, Energy, and Reactivity q Structure q Atoms q Bonding o How/Why Atoms Bond Together o Bonding Patterns q Representing molecules (putting the atoms together) o Lewis and Kekul Structures o Line-angle Formula o 3-D o Orbital Drawings q Functional Groups q Resonance
Suggested Readings (McMurry): 2.4-2.12 Suggested Problems (McMurry): 2.36-2.41, 2.43-2.51, 2.53-2.57, 2.59
Organic Chemistry
What: The study of carbon-containing compounds Why: Pervasive in nature Chemical foundation of biology Improve standard of living (medicines, plastics, pesticides . . .) How: Examine structure and analyze how it governs reactivity
Can neither accept or give up electrons easily Share e- with other carbon atoms - incredible structure diversity!
Hormone
CH3 OH
O
Amino acid
H2N
DNA base
NH2 N
Dynamite
NO2
H H HO H
OH CH3
N N
N H
O2N CH3
NO2
Estradiol
Alanine
OCH3 CH3
Adenine
TNT
OH H N O
Capsaicin (peppers)
H3C
Subtleties in Structure
CH3 OH H3C CH3 OH
HO
estradiol
testosterone
H3C
HO
H3C O
H N CH3
H N CH3
O O H3C O
H N CH3
HO
HO
codeine
morphine
heroin
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
Structure
Potential Energy
Reactivity
Potential Energy: - function of position or configuration of components - if low, compound more stable, change less likely - if high, compound less stable, change more likely
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
Structure
1. What atoms (besides carbon) are important? 2. How are these atoms bonded together?
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
80%
60%
40%
20%
Other Cl Ca K S P Mg Na O N C H
0% crude petroleum dry nonvascular plant tissue dry vascular plant tissue dry human muscle tissue Body 23% C (H20 65% mass)
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
C N O F Ne
Si
P S Cl Ar
Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr Sn Sb Te I Xe
Zr Nb Mo Tc Ru Rh Pd Ag Cd In
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
1s
2s
2p
3s
3p
1s2 1s 2s
2 1
1s22s2 1s 2s 2p
2 2 1
1s22s22p2 1s 2s 2p
2 2 3
1s22s22p4 1s 2s 2p
2 2 2 2 2 2 2 2 2 2 2 2 2 2 5
1s 2s 2p6 1s 2s 2p 3s
6 6 6 6 6 1
1s 2s 2p 3s2 1s 2s 2p 3s 3p
2 2 2 1
1s 2s 2p 3s 3p2 1s 2s 2p 3s 3p
3
1s22s22p63s23p4 1s 2s 2p 3s 3p
2 2 6 2 5
1s22s22p63s23p6
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
WHY? Attain lower ENERGY (achieved when outer shell is filled - 8 electrons)
Process of chemical bonding: adding or taking away outer shell electrons to gain a closed shell configuration
acetic acid
(H is exception to octet rule - has 1 electron) Electron Pair Domain - region of high valence shell electron density (bonding or nonbonding)
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
+ C +
+
F
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
1
H
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
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Boron
B
Electron configuration
H
H
B
H H
Special reactivity
B
H
Neutral, but electron deficient can tolerate an incomplete octet better than any other atom in the second row
Octet, but charged EN = 2, least suited of all second row elements to carry a negative charge
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
Lewis Structure
H H H C C O H H H
Kekul Structure
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H H C H
H
H C H
H H H
H H H O C C C H
C C
C C O
C C H
H H H HH H C O H C C H H C C H C H C C H C H C C H H C C H H C H H H
Iodomethane
Tyrosine
Estradiol
O H2N OH
CH3 OH
Line-Angle Formula
OH
HO
OH
OH H3C CH3
O C C
H C H C H H H
HO
CH3
H C H C H H
Incorrect! (Why?)
12
H H C H H
Line - in plane of paper Dash - going into the paper Wedge - coming out of the paper
H H H C C H H H
H C HH
HH C H
H3C
H CH3
H3C
CH3 H
Atomic Orbitals
node
13
sp3
Hybrid Orbitals
sp3 sp3
sp3 electron density distributed to the corners of a tetrahedron 180o
X
120o
Acetylene
pi orbital network
14
Functional Groups
The atoms of organic molecules exist in common combinations Each combination: unique chemical properties and reactivity behaves similarly in every organic molecule
Chemistry of every organic molecule, regardless of size or complexity, governed by functional groups
Nitrogen-Containing Oxygen-Containing
alcohol
C C OH
Sulfur-Containing
sulfide
C S C
amine
C N
nitrile alkene
C C
C C N
thiol
C C SH
alkyne diene
C C
OH
nitro
phenol
O C N O
N C C C
sulfoxide
O C S C
ether arene
imine
C O C
sulfone
O 2+ C S C O
O C C S C
epoxide
thioester
Halogen-Containing
alkyl halide
C C X
ketone
O C C C
aldehyde
O C C H
O O C C O C C
O C C O C O C C N
aryl halide
carboxylic acid
O C C OH
ester
amide
15
On to Resonance . . .
Organic Chemistry Relationship of Structure, Energy, and Reactivity q Structure Atoms Bonding How/Why Atoms Bond Together Bonding Patterns Representing molecules Lewis and Kekule Structures Line-angle Formula 3-D Orbital Drawings Functional Groups Resonance
Resonance
16
Resonance contributor
O
H H C N H
O d-
Resonance Hybrid
O d-
A Resonance Metaphor
17
+
To predict how and when two molecules will react, need to be able to predict the regions of low and high electron density
O N O
O N O
dO
dN
d-
Need a way to keep track of the changes in electron configuration between resonance contributors
Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski.
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