chapter 1 introduction and review
DESCRIPTION
Organic Chemistry , 6 th Edition L. G. Wade, Jr. Chapter 1 Introduction and Review. Definitions. Old: “derived from living organisms” New: “chemistry of carbon compounds” From inorganic to organic, Wöhler, 1828. Atomic Structure. Atoms: protons, neutrons, and electrons. - PowerPoint PPT PresentationTRANSCRIPT
![Page 1: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/1.jpg)
Chapter 1Chapter 1Introduction and ReviewIntroduction and Review
Organic Chemistry, 6th EditionL. G. Wade, Jr.
![Page 2: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/2.jpg)
Chapter 1 2
DefinitionsDefinitions
• Old: “derived from living organisms”• New: “chemistry of carbon compounds”• From inorganic to organic, Wöhler, 1828
heatNH4
+ OCN- H2N C NH2
O
urea
![Page 3: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/3.jpg)
Chapter 1 3
Atomic StructureAtomic Structure• Atoms: protons, neutrons, and electrons.• The number of protons determines the
identity of the element.• Some atoms of the same element have a
different number of neutrons. These are called isotopes.
• Example: 12C, 13C, and 14C
![Page 4: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/4.jpg)
Chapter 1 4
Electronic StructureElectronic Structure
• Electrons: outside the nucleus, in orbitals. • Electrons have wave properties.• Electron density is the probability of finding
the electron in a particular part of an orbital.
• Orbitals are grouped into “shells,” at different distances from the nucleus.
![Page 5: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/5.jpg)
Chapter 1 5
First Electron Shell
The 1s orbital holds two electrons.
Spherical shape
![Page 6: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/6.jpg)
Chapter 1 6
Second Electron Shell
Three p orbitals
P-orbital (dumbell shaped)S-Orbital (spherical)
Second shell (4 orbitals) holds total of 8 Second shell (4 orbitals) holds total of 8 electronselectrons
![Page 7: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/7.jpg)
Chapter 1 7
Electronic ConfigurationsElectronic Configurations• Aufbau principle:
Place electrons in lowest energy orbital first.
• Hund’s rule: Equal energy orbitals are half-filled, then filled.
• 6C: 1s2 2s2 2p2
![Page 8: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/8.jpg)
Chapter 1 8
Electronic Configurations
=>
![Page 9: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/9.jpg)
Chapter 1 9
Bond FormationBond Formation
• Ionic bonding: electrons are transferred.• Covalent bonding: electron pair is shared.
![Page 10: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/10.jpg)
Chapter 1 10
Lewis StructuresLewis Structures• Bonding electrons represented by a dash line
or a pair of electron• Nonbonding electrons or lone pairs are shown
Satisfy the octet rule!
C
H
H
H
OH
C :....: O:HH
H
H
..
..
![Page 11: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/11.jpg)
Chapter 1 11
Multiple Bonding
=>
![Page 12: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/12.jpg)
Chapter 1 12
Dipole MomentDipole MomentAmount of electrical charge x bond length.
![Page 13: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/13.jpg)
Chapter 1 13
Electronegativity and Bond PolarityElectronegativity and Bond Polarity
Greater EN means greater polarity
=>
![Page 14: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/14.jpg)
Chapter 1 14
Calculating Formal ChargeCalculating Formal ChargeFor each atom in a valid Lewis structure:• Count the number of valence electrons• Subtract all its nonbonding electrons• Subtract half of its bonding electrons
C
H
H
H
C
O
O P
O
OO
O
3-
F.C = # valence e – (non-bonding e + 1/2(bonding e)
![Page 15: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/15.jpg)
Chapter 1 15
Ionic StructuresIonic Structures
C
H
H
H N
H
HH
+
Cl-
Na O CH3 or O CH3Na+ _X
=>
If the EN is greater than 2.5, the bond is a ionic bond.
![Page 16: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/16.jpg)
Chapter 1 16
ResonanceResonance• Only electrons can be moved (usually
lone pairs or pi electrons).• Nuclei positions and bond angles remain
the same.• The number of unpaired electrons
remains the same.• Resonance causes a delocalization of
electrical charge.
![Page 17: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/17.jpg)
Chapter 1 17
Resonance Example
• The real structure is a resonance hybrid.• All the bond lengths are the same.• Each oxygen has a -1/3 electrical charge.
N
O
OO
_ _
N
O
OO
_
N
O
OO
![Page 18: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/18.jpg)
Chapter 1 18
Major Resonance Form or Major Resonance Form or Major ContributorMajor Contributor
• has as many octets as possible.• has as many bonds as possible.• has the negative charge on the most
electronegative atom.• has as little charge separation as
possible.
![Page 19: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/19.jpg)
Chapter 1 19
Resonance Hybrid
majorcontributor
minor contributor, carbon does
not have octet=>
![Page 20: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/20.jpg)
Chapter 1 20
Chemical FormulasChemical Formulas
• Full structural formula (no lone pairs shown)
• Line-angle formula
• Condensed structural formula
• Molecular formula• Empirical formula
CH3COOH
C2H4O2
CH2O
C
H
H
H
C
O
O H
OH
O
![Page 21: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/21.jpg)
Chapter 1 21
Calculating Empirical FormulasCalculating Empirical Formulas
• Given % composition for each element, assume 100 grams.
• Convert the grams of each element to moles.
• Divide by the smallest moles to get ratio.• Molecular formula may be a multiple of
the empirical formula.
![Page 22: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/22.jpg)
Chapter 1 22
Sample ProblemAn unknown compound has the following composition: 40.0% C, 6.67% H, and 53.3% O. Find the empirical formula.
molCmolCgCgC 33.3/0.12
0.40
molHmolHgHgH 60.6/01.1
67.6
molOmolOgOgO 33.3/0.16
5.53
3.33
3.33
3.33
= 1
= 1
= 1.98 = 2
Empirical Formula: CH2O
![Page 23: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/23.jpg)
Chapter 1 23
Arrhenius Acids and BasesArrhenius Acids and Bases
• Acids dissociate in water to give H3O+ ions.• Bases dissociate in water to give OH- ions.• Kw = [H3O+ ][OH- ] = 1.0 x 10-14 at 24°C
• pH = -log [H3O+ ]• Strong acids and bases are 100%
dissociated.
1 M1 MCl
-+H3O
+H2O+HCl
![Page 24: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/24.jpg)
Chapter 1 24
BrBrØØnsted-Lowry Acids and Basesnsted-Lowry Acids and Bases
• Acid: donates a proton.• Base: accepts a proton.• Conjugate acid-base pairs.
CH3 C
O
OH + CH3 NH2 CH3 C
O
O- + CH3 NH3+
acid conjugatebase
base conjugateacid
=>
![Page 25: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/25.jpg)
Chapter 1 25
Acid and Base StrengthAcid and Base Strength
• Acid dissociation constant, Ka
• Base dissociation constant, Kb
• For conjugate pairs, (Ka)(Kb) = Kw
• Spontaneous acid-base reactions proceed from stronger to weaker.
CH3 C
O
OH + CH3 NH2 CH3 C
O
O- + CH3 NH3+
pKa 4.74 pKb 3.36 pKb 9.26 pKa 10.64
![Page 26: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/26.jpg)
Chapter 1 26
Structural Effects on AcidityStructural Effects on Acidity
• Electronegativity • Size • Resonance stabilization of conjugate
base
![Page 27: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/27.jpg)
Chapter 1 27
ElectronegativityElectronegativityAs the bond to H becomes more polarized, H becomes more positive and the bond is easier to break.
=>
![Page 28: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/28.jpg)
Chapter 1 28
SizeSize• As size increases, the H is more loosely
held and the bond is easier to break.• A larger size also stabilizes the anion.
![Page 29: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/29.jpg)
Chapter 1 29
ResonanceResonance• Delocalization of electron pairs.• More resonance structures usually
mean greater stabilization.
CH3CH2OH < CH3C
O
OH < CH3 S
O
O
OHAcidity:
![Page 30: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/30.jpg)
Chapter 1 30
Lewis Acids and BasesLewis Acids and Bases• Acids accept electron pairs = electrophile• Bases donate electron pairs = nucleophile
=>
![Page 31: Chapter 1 Introduction and Review](https://reader035.vdocuments.net/reader035/viewer/2022062520/56815e81550346895dcd1156/html5/thumbnails/31.jpg)
Chapter 1 31
End of Chapter 1