wade powerpoint/lecture for chapter 1
DESCRIPTION
This is a detailed powerpoint for everything that is covered in this chapter of Wade's Organic Chemistry textbook. It goes through all the key concepts and has helped me excel in this chapter of Organic Chemistry. I recommend going through this lecture powerpoint if you are trying to prepare for the ACS exam or simply for an exam in your class.TRANSCRIPT
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Chapter 1Introduction and
Review
Organic Chemistry , 8th Edition
L. G. Wade, Jr.
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Organic Chemistry Definition:
• Old: “derived from living organisms”
• New: “ chemistry of caron
compounds”
• !riedrich "#hler$s 1%&%
synthesis of urea signaledthe end of “vitalism'” heat
NH4
+ OCN
- H2 N C NH2
O
urea
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Organic Chemistry
"hy do we distinguish etween
inorganic and organic compounds(
"hy are organic compoundsimportant(
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)tomic *tructure• )toms: protons+ neutrons+ and electrons'
• ,he numer of protons determines theidentity of the element'
• *ome atoms of the same element have adifferent numer of neutrons' ,hese arecalled isotopes'
• -.ample: 1& C+ 1/C+ and 10C
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-lectron roperties
• -lectrons have wave properties'
• In the 12&3s+ 4uantum 5echanics wasestalished as a theory to e.plain the wave
properties of electrons'• ,he solution to wave e6uations for electrons
provides us with visual pictures called oritals'
• Oritals are grouped into “ shells+” at differentdistances from the nucleus'
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• ,he type or orital e identified y its shape
• )n orital is a region where there is a calculated237 proaility of finding an electron' ,heremaining 137 proaility tapers off as youmove away from the nucleus
-lectron roperties
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!irst -lectron *hell
,he 1s orital holds two electrons'
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*econd -lectron *hell
2s orbital (spherical)
,hree p oritals
2 p orbital
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-lectron Configurations
• )ufau principle: laceelectrons inlowest energy
orital first'• 8und$s rule:
-6ual energyoritals are half9
filled+ then filled'
• C: 1s& &s& &p&
↑↓
↑↓
↑ ↑
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-lectron Configurations
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;ond !ormation
• Ionic onding: electrons aretransferred'
• Covalent onding: electron pair isshared'
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<ewis Dot *tructures
• ;onding electrons
• Nononding electrons or lone pairs
Satisfy the octet rule!
C
H
H
H
OH
onding electrons
nononding electrons
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='N' <ewis“the most rilliant scientist to never
win a Noel ri>e”
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Lewis’s1902lecture
notesshowing hisidea of
“cubicalatoms” –which later
became
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*imple <ewis *tructures
• !or simple <ewis *tructures?1' Draw the individual atoms using dots to
represent the valence electrons'
&' ut the atoms together so they share )IR*of electrons to ma@e complete octets' "8),is an octet(
• ,a@e N8 / + for e.ample?
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ro' 19&' Draw <ewisstructures for
f' dimethyl ether
g' fluoroethane
h' oron trifluoride
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Representing 5ultiple ;onds
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*ome 5ore 5ultiple ;ond<ewis *tructures
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ro' 19/' Draw <ewis structures forthe following molecular formulas'
e' 8 & CN8
h' 8NN8
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Aalence
• ,he numer of onds an atomusually forms'
C N O H F :
:
: :
:
:
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-lectronegativity
•,he aility of an atom toattract electrons to itself ina chemical ond'•One of the most important
concepts in OrganicChemistry ecause?
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electronegatiit!
bond "olarit!
molecular sha"efrom #$%&R
molecular di"ole moment
intermolecular attractie forces
&'($)*+L &RO&%R,)%$ O- OL%*
ector addition
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Chapter 1
Dipole 5oment • )mount of electrical charge . ond length'
• Charge separation shown y electrostatic potential map B-5'
• Red indicates a partially negative region and lue indicates a partially positive region'
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Chapter 1
-lectronegativity and;ond olarity
=reater electronegativity differencemeans greater ond polarity'
"hat element formsthe most polar ond
with caron(
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,ypes of Chemical ;onds
• Depend on differences inelectronegativities'
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!ormal Charge
• ) method of @eeping trac@ ofcharges'
• *hows what charge would eon what atom in a particular
<ewis structure'
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"hy !ormal Charge(
• the most stale <ewis structurewill e the one with
?>ero formal charge'?the negative charge on themost electronegative atom'
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Calculating !ormal Charge
• !or each atom in a valid <ewisstructure:
• Count the numer of valence electrons
• *utract all its nononding electrons• *utract half of its onding electrons
C
H
H
H
C
O
O P
O
OO
O
3-
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Ionic *tructures
C
H
H
H N
H
H
H
+
Cl-
Na O CH3 or O CH3 Na+ _
X
,he N will have a 1formal charge
*alts E compounds of metalsand nonmetals E are ionic'
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carocationcaranion
6uaternary ammoniumion
hydro.ideor [email protected]
halideion
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Resonance
• "hen molecules or ions showcharacteristics of & or more valence
ond B<ewis dot structures whichdiffer from each other only in the placement of electrons'
• )nother of the maFor concepts inOrganic ChemistryG
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Resonance *tructures
• Only electrons can e moved Busuallylone pairs or pi electrons'
• Nuclei positions and ond angles
remain the same'• ,he numer of unpaired electrons Bif
any remains the same'
• Resonance causes a delocali>ation ofelectrical charge'
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Resonance -.ample
• ,he real structure is a resonance hyrid '•
)ll the ond lengths are the same'• -ach o.ygen has a 91H/ electrical charge'
N
O
OO
_ _
N
O
OO
_
N
O
OO
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*ome -.amples of Resonance inOrganic Chemistry
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,he 5aFor Resonance !orm
• has as many octets as possile'
• has as many onds as possile'
• has the negative charge on themost electronegative atom'
•has as little charge separation as possile'
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Resonance 8yrid
maFor contriutor
minor contriutor+caron does
not have octet
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*olved ro' 19&' !or each compound+draw the important resonance forms+
indicate which is the maFor contriutor+and whether all the forms have the same
energy'
a C8 /OC8 & J
C C
O
HH
H.. _
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Chemical !ormulas
• !ull structural formulaBno lone pairs shown
• <ine9angle formula
• Condensed structuralformula
• 5olecular formula
• -mpirical formula
• C8 /COO8
• C & 8 0O &
• C8 & O
C
H
H
H
C
O
O H
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rolem' *how the <ewis structure andline angle formula for the following
compounds'
a propane+ C /8 %
cycloutane+ C 08 %
c acetone+ C8 /CBOC8 /
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)rrhenius )cids and ;ases
• )cids dissociate in water to give 8 / O D ions'
• ;ases dissociate in water to give O8 9 ions'
• K w L 8 / O D JO8 9 J L 1'3 . 13 910 at &0MC
• p8 L 9log 8 / O D J
• *trong acids and ases are 1337dissociated'
1 M 1 M
Cl-+H3O+
H2O+HCl
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• issertation wor3 onconductiities ofelectrol!te solutions wasawarded lowest "assinggrade4 but was laterawarded the 1905 6obel&ri7e in *hemistr!8• &ro"osed the rstdenitions of acids andbases in 1::;.• -ormulated the conce"tof actiation energ! in
chemical r<ns.• &ro"osed his“greenhouse law” lin3ingatmos"heric leels of *O2
to earth’s tem"erature.'e was the “discoerer”
of global warming8
FYI: Svante Arrhenius (18"1#$%
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;r nsted9<owry )cids
and ;ases• )cids can donate a proton'
• ;ases can accept a proton'
• ConFugate acid9ase pairs'
CH3 C
O
OH + CH3 NH2 CH3 C
O
O-
+ CH3 NH3+
acid conFugatease
ase conFugateacid
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5edical -.ample:
acid
ase
conFugate acid
conFugatease
Not asored in the
acidic stomach
)sored in theasic intestines
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*tructural -ffects
on )cidity • -lectronegativity
• *i>e• Resonance staili>ation of conFugate
ase
-l t ti it ) idit f
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Chapter 1
-lectronegativity )cidity of*econd Row 8ydrides
)s the ond to 8 ecomes more polari>ed+ 8 ecomes more positive andthe ond is easier to rea@'
) i *i ) idit f th
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Chapter 1
)nion *i>e )cidity of the8alogen 8ydrides
• )s anion si>e increases+ the 8 is moreloosely held and the ond is easier to rea@'
• ) larger si>e also staili>es the anion'
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Resonance )cidity •
Delocali>ation of the negative charge on the conFugatease will staili>e the anion+ so the sustance will e astronger acid'
• 5ore anionic resonance structures usually mean greaterstaili>ation and+ therefore+ more acidic B i'e' the anion
forms easier+ faster'
CH3CH2OH < CH3C
O
OH < CH3 S
O
O
OH
DRAW THE ANIONS OF THESE ACIDS.
< i ) id d ;
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<ewis )cids and ;ases• <ewis acids accept electron pairs
L electrophile• <ewis ases donate electron pairs
L nucleophile
C d )
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Curved )rrows
• "e use curved arrows to show
electron movement
• Curved arrows generally show electron
movement for pairs of electrons,he arrow starts where the electrons are
currently located
,he arrow ends where the electrons will end
up after the electron movement
C
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Curved )rrows in Resonance
• Rule 1: never rea@ a single ond
• *ingle onds can rea@+ ut NO, in R-*ON)NC-
• Resonance occurs for electrons e.isting inoverlapping p oritals+ ut not in hyrid atomicoritals+ e'g' sp+ sp& + or sp/ '
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Curved )rrows in Resonance
Rule &: Never e.ceed an octetfor & nd row elements B;+ C+ N+ O+ !
• -.amples of arrows that violate Rule &'
=ood arrow or ad arrow(
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Important DefinitionsG
• -lectrophile E “lover of electrons”P willhave a partial or formal positive charge+ e'g' 8 ;r or R /C '
• Nucleophile E “nucleusHpositivecharge lover”P will have a partial or
formal negative charge+ e'g' N R / or E
O8'
̤
1 12 1 D t i hi h i
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ro' 1912' 1 Determine which species areacting as electrophiles Bacids and which
are acting as nucleophiles Bases'& Qse the curved arrow formalism to showthe movement of electron pairs in thesereactions'
/ Indicate which reactions are est termed;ronsted9<owry acid9ase r.ns'
aCH3 H
O+ HCl
CH3 H
O+
H
+ Cl-
ro 1912 1 Determine which species are acting as electrophiles
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ro' 1912' 1 Determine which species are acting as electrophilesBacids and which are acting as nucleophiles Bases'& Qse the curved arrow formalism to show the movement of electron
pairs in these r.ns'
/ Indicate which r.ns are est termed ;ronsted9<owry acid9aser.ns'
CH3 H
O
+ CH3O-
CH3
O-
O CH3
H
f CH
3 NH
2 + CH
3 Cl CH
3 NH
2
+CH
3 + Cl
-
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,he -nd