A1257787121RFcWY

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CHEMISTRY 351
Fall 2005
ORGANIC CHEMISTRY
Professor Donald Pavia
Lecture MTWF 9 SL 130
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http//atom.chem.wwu.edu/dept/wwuchem.html
CHEMISTRY WEB SITE
Course Materials Pavia Chem 351
COURSE WEB SITE
http//atom.chem.wwu.edu/dept/facstaff/pavia/351pa
via.html
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SOME ADVICE ON STUDYING FOR ORGANIC CHEMISTRY
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STRUCTURE OF KNOWLEDGE IN ORGANIC CHEMISTRY
Builds like a pyramid balanced on its point.
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If something is missing ..
The whole structure collapses !!!
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MATERIAL IN THIS COURSE IS CUMULATIVE
STUDY TO UNDERSTAND THE MATERIAL
The material keeps building on itself.
ANYTHING THAT YOU DO NOT MASTER WILL COME BACK TO
HAUNT YOU LATER
You literally cannot forget anything in this
course.
WE WILL BUILD ON EARLIER TOPICS TO DEVELOP NEW
ONES
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IF YOU DONT UNDERSTAND SOMETHING .. GET HELP AS
SOON AS YOU CAN
See me after class, during office hours, or
make an appointment.
DO AS MANY PROBLEMS AS YOU CAN FIND TIME FOR IN
YOUR SCHEDULE
Active learning is more effective than passive
study.
Doing problems really cements your
understanding it requires you to apply what you
learn.
THE END-OF-CHAPTER PROBLEMS ARE THE MOST HELPFUL
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STRANGE BUT TRUE
We retain 90 of what we say
as we do a thing
70 of what we say as we talk
50 of what we see and hear
30 of what we see
20 of what we hear
10 of what we read
ACTIVE
PASSIVE
.. a psychological study
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DONT GET BEHIND !!!!
Although the very early material is easy, or
even simple review material for you, things will
get more difficult very quickly.
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Every day you dont practice means youre a
day farther from getting good.
Ben Hogan, golf champion
The greatest reward for doing is the
opportunity to do more.
Jonas Salk, inventor of polio vaccine
Success comes before work only in the
dictionary.
Anonymous
I hear and I forget, I see and I remember, I do
and I understand.
Anonymous
If youre are going through hell, keep going.
Winston Churchill
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QUICK REVIEW OF GENERAL CHEMISTRY STUFF
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ATOMIC STRUCTURE
AUFBAU PRINCIPLE
- Hund Rule - Pauli Exclusion Principle
ELECTRONIC CONFIGURATIONS OF ATOMS
Review in your general chemistry text is suggested
Ebbing and Gammon Chapters 7 and 8
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CORRECT ORDER OF FILLING FOR THE FIRST THIRTY
ATOMS
E N E R G Y
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Electronic Configurations of First Eleven Elements
H 1 1s1 CORE VALENCE SHELL He 2 1s2 Li 3 1s22
s1 1s22s1 Be 4 1s22s2 1s22s2 B 5 1s22s22p1
1s22s22px1 C 6 1s22s22p2 1s22s22px12py1 N 7
1s22s22p3 O 8 1s22s22p4 F 9 1s22s22p5 Ne 10 1s2
2s22p6 Na 11 1s22s22p63s1 1s22s22p63s1
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LEWIS DOT SYMBOL
VALENCE ELECTRONS
.
Be
.
CORE
Be 1s22s2
CORE VALENCE ELECTRONS
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D Block
S and P Blocks
Transition Metals B group elements
Main Groups or A group elements
1A 2A
3A 4A 5A 6A 7A 8A
(1)
(18)
He
H
PERIODIC
TABLE
1
(2)
(13) (14) (15) (16) (17)
Be
Li
Ne
F
O
N
C
B
2
Mg
Na
Ar
Cl
S
P
Si
Al
3
(3) (4) (5) (6) (7)
(8) (9) (10) (11) (12)
Ca
K
Sc
Ti
V
Kr
Br
Se
Ge
Co
Ga
As
Cr
Mn
Fe
Ni
Cu
Zn
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Sr
In
Sn
Sb
Rb
Y
Zr
Xe
I
Ag
Cd
Mo
Nb
Tc
Ru
Rh
Pd
Te
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Cs
Ba
Lu
Hf
Rn
At
W
Ta
Ir
Pt
Au
Hg
Pb
Bi
Po
Re
Os
Tl
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Fr
Ra
Lr
Rf
Db
Sg
Bh
Hs
Mt
Ds
Uuu
Uub
Uut
Uuq
Uup
Uuh
Uus
Uuo
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lanthanides
La
Ce
Pr
Pm
Sm
Eu
Gd
Tb
Dy
Ho
Er
Tm
Yb
Nd
actinides
Ac
Es
Fm
Md
No
Am
Cm
Bk
Cf
Th
Pa
U
Np
Pu
The traditional system designates groups as A
(main) or B (transition).
The modern system (IUPAC) now uses 1 - 18 in
sequence.
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Table 1-2 in text
The A groups are regular.
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A SIMPLE COVALENT BOND
A pair of electrons is shared between the two
bonded atoms.
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A SIMPLE COVALENT BOND
Bonded pair
H
H
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A LEWIS DIAGRAM
..
(note use of lines for bonds)
H
O
H
..
COVALENT BONDS
CONSTRUCTED FROM LEWIS DOT SYMBOLS
..
.
.
.
.
H
..
H
O
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METHANE
DOTS AND CROSSES METHOD
H
CH4
.
x
.
.
C
H
H
x
x
x
.
H
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DRAWING CONVENTIONS
1. A shared pair (bond) is drawn as a line.
C O
( not as CO )
2. An unshared pair is shown as a pair of dots.
N
3. The diagram includes formal charges (later).
..

H O H
USE THESE
H
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CARBON DIOXIDE
.
..
..
.
.
.
.
.
.
O
O
C
..
..
.
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DOTS AND CROSSES
This method of forming Lewis Diagrams
could facetiously be called the Dots and
Crosses method.
This method has real limitations.
We will learn an alternate method, which is more
general, in the next set of slides.
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.
x
DOTS AND CROSSES DONT WORK WELL FOR LARGE
MANY-ATOM MOLECULES .
WE NEED A DIFFERENT METHOD
WHICH FOLLOWS ..
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CONSTRUCTING LEWIS DIAGRAMS A
NEW METHOD
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DRAWING LEWIS DIAGRAMS
4. Assign the remaining electrons following the
Lewis Rules.
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LEWIS RULES (a reminder)
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LEWIS RULES ...... continued
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REVIEW OF METHOD
1. Determine the total number of valence
electrons in the molecule or ion.
2. Determine the arrangement of the atoms
(the skeleton).
3. Subtract the electrons used in the skeletal
bonds ( 2 electrons each bond ) from the total.
4. Assign the remaining electrons following the
Lewis Rules (octets, duets, bonds, pairs etc.).
5. Check that the total number of electrons is
correct ( count them ! ).
Do CO2 or H(CO)Cl