Chapter 1-12: Org I review
Transcript of Chapter 1-12: Org I review
Chapter 1-12: Org I review
Topic I. Structure and Bonding
NO
NHOH OH
OH
O
F
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• Carbon§Group #: 4A§Atomic #: 6§Element symbol: C§Elemental name: carbon§Atomic weight: 12.011§Electron distribution: 1s2 2s22p2
• Carbon: the most important element to life!§ Blood: various minute by minute§ Bone: 0.8%§ Tissue: 67%§ Total amount in body: 16 kg
Only carbon forms strong single bond to itself that are stableenough to resist chemical attack under ambient conditions
Topic I. Structure and Bondingq Bonding: the joining of two atoms in stable arrangement.
Some key concepts: (hope you know themJ)
Lewis Structures; Bond length; Bond angle; Geometry; Hybridization; S-factor
Formal Charge; Valency; Degree of unsaturation
Topic I. Structure and Bondingq Bond length
H-H 0.74 H-F 0.92 C-F 1.33
C-H 1.09 H-Cl 1.27 C-Cl 1.77
Topic I. Structure and BondingSome key concepts: (hope you know themJ)
Lewis Structures; Bond length; Bond angle; Geometry
• Bond Angle
– Linear 180o
– Trigonal planar 120o
– Tetrahedral 109.5o
Topic I. Structure and BondingGeometry; Hybridization; S-factor
C-C Bond length (Å) strength (kcal/mol)CH3-CH3 1.53 88CH2=CH2 1.34 152CHΞCH 1.21 200
C-H Bond length (Å) strength (kcal/mol)CH3-H 1.11 98CH2=CH-H 1.10 104CHΞC-H 1.09 125
Topic I. Structure and BondingValence Electrons Formal Charge (Electron ownership) (Valence)
Topic I. Structure and BondingValence Electrons Formal Charge (Electron ownership) (Valence)
Formal Charge = valence electrons – electron owned
valence = # of bonds – formal charge
Topic I. Structure and BondingFormal Charge = valence electrons – electron owned
Valence = # of bonds – formal charge
q Degree of Unsaturation
C6H5NO2
C7H12O2
DOU =Σ(v-2) + 2
2= #C x 2 - #H - #X + #N +2
2
Topic II. Resonance and InductiveEDG vs EWG (simple rule: only the first atom matter)
Topic II. Resonance and Inductiveq Resonance: Re-allocation of electrons
n Single resonance structure does not represent the structure of a molecules, only the hybrid/combination does.
n Resonance structures are not in equilibrium. They are the different formats of a same molecule.
n Resonance structure are not isomers.
q Inductive: Electron-donative group (EDG) vs Electron-withdrawing group (EWG)
Topic II. Resonance and Inductiveq Resonance: Re-allocation of electrons
Topic II. Resonance and InductiveOctet rule
H3C Me
O
SO
e= 21
e= 47
Topic III. Curved arrow electron pushingHow to draw curved arrow notation:
Where to start: pair of electrons
Where to go: how or something can move
Topic III. Curved arrow electron pushingHow to draw curved arrow notation:
Topic III. Curved arrow electron pushingHow to draw curved arrow notation:
C C C CH2
H
+
Topic IV. Acid and Base ChemistryAcid/Base reaction
HA H+ + A-Keq
Chemistry 2211 Spring 2021
pKa Values
Other pKa sources:
• http://www.chem.wisc.edu/areas/reich/pkatable/ • http://daecr1.harvard.edu/pdf/evans_pKa_table.pdf • http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf
H3O+ 0
R OH
O5
OH
CH3OH
H2O
R CH2
O
R CH2
O O
R
R
RN H
R
RC HR
HC C
H
RR
R
R H
R
RN+ HR
16
16
10
20
10
45
40
25
35
10
H2 35
HO OH
S HR
12
11
H
Topic IV. Acid and Base Chemistry
HA H+ + A-Keq
Chemistry 2211 Spring 2021
pKa Values
Other pKa sources:
• http://www.chem.wisc.edu/areas/reich/pkatable/ • http://daecr1.harvard.edu/pdf/evans_pKa_table.pdf • http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf
H3O+ 0
R OH
O5
OH
CH3OH
H2O
R CH2
O
R CH2
O O
R
R
RN H
R
RC HR
HC C
H
RR
R
R H
R
RN+ HR
16
16
10
20
10
45
40
25
35
10
H2 35
HO OH
S HR
12
11
H
Acid Strength: Resonance and inductive
O
OHH3C
OHH3C OH
O
H3C
O
CH3 H3C
O
CH3
O
H3C
O
CH3
O
H3C
O
OCH3
O
H3CO
O
OCH3
Topic IV. Acid and Base ChemistryChemistry 2211 Spring 2021
pKa Values
Other pKa sources:
• http://www.chem.wisc.edu/areas/reich/pkatable/ • http://daecr1.harvard.edu/pdf/evans_pKa_table.pdf • http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf
H3O+ 0
R OH
O5
OH
CH3OH
H2O
R CH2
O
R CH2
O O
R
R
RN H
R
RC HR
HC C
H
RR
R
R H
R
RN+ HR
16
16
10
20
10
45
40
25
35
10
H2 35
HO OH
S HR
12
11
H
O
H3C
O
CH3 H3C
O
CH3
O
H3C
O
CH3
O
H3C
O
OCH3
O
H3CO
O
OCH3
Topic IV. Acid and Base ChemistryChemistry 2211 Spring 2021
pKa Values
Other pKa sources:
• http://www.chem.wisc.edu/areas/reich/pkatable/ • http://daecr1.harvard.edu/pdf/evans_pKa_table.pdf • http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf
H3O+ 0
R OH
O5
OH
CH3OH
H2O
R CH2
O
R CH2
O O
R
R
RN H
R
RC HR
HC C
H
RR
R
R H
R
RN+ HR
16
16
10
20
10
45
40
25
35
10
H2 35
HO OH
S HR
12
11
H
H H H
Topic IV. Acid and Base ChemistryHA1 HA2 + A1-
Keq+ A2-
Topic IV. Acid and Base ChemistryHA1 HA2 + A1-
Keq+ A2-
O
OHH3C+ Na OMe
O
O NaH3C+ HOMe
Keq
Q: What is the Keq? What is DG?
Topic V. Stereo chemistryIsomers: different compounds with the same molecular formula
Constitutional isomers
StereoisomersDiastereomers
Enantiomers
Topic V. Stereo chemistry
• Chiral and AchiralChiral: a molecule that is not superimposable on its mirror
Topic V. Stereo chemistry
• Chiral and Achiral• Chiral and Achiral
H
H FCl
H
HFCl
H
H FCl
H
H FCl
Topic V. Stereo chemistry
Br
H FCl
Br
HFCl
H
Br FCl
Br
H FCl
Topic V. Stereo chemistryBr
H FCl
H
H FCl
F
Cl
H
H
Br
H FCl
F
Cl
Br
H
Topic V. Stereo chemistry• Chair conformation:
Topic VI. Others• Four key types of reactions:
SN1 vs SN2 E1 vs E2
Topic VI. Others• Oxidation state:
H CH
HH
[O]
[H]H CH
HO
[O]
[H]H O
H
H [O]
[H]O
H
HO [O]
[H]C OO
H HH HH H
[O]
[H]
[O]
[H]
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