Organic Chemistry II CHEM 2211

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Transcription:

Organic Chemistry II CEM 2211 Dr. Xiaodong Michael Shi TR, 6:30 pm--7:45 pm

Topic I. Structure and Bonding O N N O O O O F Atorvastatin (Lipitor): best selling drug in the world (> $13 billion per year)

Topic I. Structure and Bonding Carbon Group #: 4A Atomic #: 6 Element symbol: C Elemental name: carbon Atomic weight: 12.011 Electron distribution: 1s 2 2s 2 2p 2 Carbon: the most important element to life! Blood: various minute by minute Bone: 0.8% Tissue: 67% Total amount in body: 16 kg

Topic I. Structure and Bonding Only carbon forms strong single bond to itself that are stable enough to resist chemical attack under ambient conditions

Topic I. Structure and Bonding q Bonding: the joining of two atoms in stable arrangement. Lewis Structures Bond Length Bond Angle Geometry Formal Charge And

Topic I. Structure and Bonding q Formal Charge Knowing the following key #: Valence electrons: Electron ownership:

Topic I. Structure and Bonding q Formal Charge Knowing the following key #: Valence electrons: Electron ownership: Electron ownership: Unshared electrons + ½ of shared electrons Formal charge = # of valence electron electron owns

Topic I. Structure and Bonding q Formal Charge O C 3 O C 3 O C 2

Topic I. Structure and Bonding q Formal Charge NO 2

Topic I. Structure and Bonding q Octet rule O 3 C Me ε= 21 O S ε= 47

Topic I. Structure and Bonding q Degree of Unsaturation DOU = Σ(v-2) + 2 2 = #C x 2 - # - #X + #N +2 2

Topic I. Structure and Bonding q Degree of Unsaturation DOU = Σ(v-2) + 2 2 = #C x 2 - # - #X + #N +2 2 C 7 12 O 2 C 6 5 NO 2

Topic I. Structure and Bonding q Degree of Unsaturation DOU = Σ(v-2) + 2 2 = #C x 2 - # - #X + #N +2 2 C 6 5 NO 2

Topic I. Structure and Bonding q 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. NO 2

Topic I. Structure and Bonding q Resonance: Re-allocation of electrons

Topic I. Structure and Bonding q Bond length - 0.74 -F 0.92 C-F 1.33 C- 1.09 -Cl 1.27 C-Cl 1.77

Topic I. Structure and Bonding Bond strength and bond length (C-C) Bond length (Å) strength (kcal/mol) C 3 -C 3 1.53 88 C 2 =C 2 1.34 152 CΞC 1.21 200

Topic I. Structure and Bonding Bond Angle Linear 180 o Trigonal planar 120 o Tetrahedral 109.5 o

Topic I. Structure and Bonding Bond Angle Linear 180 o Trigonal planar 120 o Tetrahedral 109.5 o

Bond Angle Topic I. Structure and Bonding

Topic I. Structure and Bonding ybridization: SP3, SP2, SP s factor

Topic I. Structure and Bonding Bond strength and bond length (C-) Bond length (Å) strength (kcal/mol) C 3-1.11 98 C 2 =C- 1.10 104 CΞC- 1.09 125

Topic I. Structure and Bonding Electronic donating and Electron Withdrawing group (EDG vs EWG)

Topic I. Structure and Bonding Electronic donating and Electron Withdrawing group (EDG vs EWG)

Topic II. Curved arrow electron pushing Curved arrow notation for electron moving

Topic II. Curved arrow electron pushing ow to draw curved arrow notation: Where to start: pair of electrons Where to go: how or something can move

Topic II. Curved arrow electron pushing ow to draw curved arrow notation: Where to start and where to go!

Topic II. Curved arrow electron pushing ow to draw curved arrow notation: Where to start and where to go!

Topic II. Curved arrow electron pushing ow to draw curved arrow notation: Where to start and where to go!

Topic II. Curved arrow electron pushing ow to draw curved arrow notation: Where to start and where to go!

Topic II. Curved arrow electron pushing ow to draw curved arrow notation: Where to start and where to go! C C + C C 2

Topic II. Curved arrow electron pushing ow to draw curved arrow notation: Where to start and where to go!

Topic III. Acid and Base Chemistry Acid/Base reaction Keq A + + A -

Topic III. Acid and Base Chemistry Acid/Base reaction A 1 A 2 + A 1 - Keq + A 2 -

Topic III. Acid and Base Chemistry Acid/Base reaction 3 C O O + Na OMe Keq 3 C O O Na + OMe Q: What is the Keq? What is ΔG?

Topic III. Acid and Base Chemistry Acid/Base reaction

Topic III. Acid and Base Chemistry Acid strength and pka Resonance effect and inductive effect 3 C O O O 3 C O

Topic III. Acid and Base Chemistry Acid strength and pka O O O 3 C C 3 3 C C 3 O O O O O O 3 C C 3 3 C OC 3 3 CO OC 3

Topic III. Acid and Base Chemistry Acid strength and pka ybridization effect

Isomers Topic IV. Stereochemistry Isomers: different compounds with the same molecular formula Constitutional isomers Stereoisomers Diastereomers Enantiomers

Topic IV. Stereochemistry Isomers C 3 C=CC 3

Chiral and Achiral Topic IV. Stereochemistry Chiral: a molecule that is not superimposable on its mirror

Topic IV. Stereochemistry Chiral and Achiral Cl F Cl F Cl F Cl F

Topic IV. Stereochemistry Chiral and Achiral Br Cl F Br Br Cl F Cl F Br Cl F

Topic IV. Stereochemistry Stereogenic Center Br Cl F Br Cl F Cl F Br Cl Cl F F

Newnam Projection Topic V. Others eclipsed staggered

Topic V. Others Chair conformation:

Topic V. Others Chair conformation:

Topic V. Others Four key types of reactions: SN1 SN2 E1 E2

Topic V. Others Oxidation state: C [O] [] C O [O] [] O [O] [] O O [O] [] O C O [O] [] [O] []

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