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]

I survived!!!

• Class note;

• Homework/problem set;

• Practice.