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Exam 2
Lecture Set 1-6, Emphasis on 4-6
44
Organic Chemistry
Undergraduate 2
10/22/2012

Additional Organic Chemistry Flashcards

 


 

Cards

Term
Lewis Acid
Definition
Accepts electrons
Term
Lewis Base
Definition
Donates electrons
Term
Anion Stability
Definition
Size
EN
Hybridization
Resonance
Inductive Effect
Term
Higher Boiling Point
Definition
Higher IMF
Heavier
Branching
Term
Staggered Newman Projection
Definition
More stable
Less energy
Term
Eclipsed Newman Projection
Definition
Less stable
More energy
Term
E1
Definition
Dehydration
Carbocation intermediate
Term
E2
Definition
Dehydrohalogenation
Concerted
Term
Heat of Combustion
Definition
Stability of alkanes
More branched = more stable = low heat
Term
Heat of Hydrogenation
Definition
Stability of alkenes
More substituents = more stable = low heat
Term
Hydrogenation
Definition

H2/Pd

 

Syn addition

No rearrangement

H, H

Term
Hydrohalogenation
Definition
HX

Markovnikov
Mixture addition
Can rearrange
H, X
Term
Hydrohalogenation with Peroxides
Definition
HX/peroxides

Anti-Markovnikov
Mixture addition
No rearrangement
H, X
Term
Hydration
Definition
H2SO4/HOR

Markovnikov
Mixture addition
Can rearrange
H, OR
Term
Halogenation
Definition
X-X'

Markovnikov
Anti addition
No rearrangement
X, X'
Term
Halohydrin
Definition
X-X/HOR

Markovnikov
Anti addition
No rearrangment
X, OR
Term
Hydroboration/Oxidation
Definition
BH3,THF/H2O2,OH,H2O

Anti-Markovnikov
Syn addition
No rearrangement
H, OH
Term
Oxymercuration/Reduction
Definition
Hg(OAc)2,H2O/NaBH4

Markovnikov
Mixture
No rearrangement
H, OH
Term
Epoxidation
Definition
Product: triangle with oxygen at top center

No rearrangement
Term
Cyclopropanation
Definition
KOC(CH3)3/CHCl3 produces triangle with 2 Cl at top

Zn(Cu)/CH2I2 produces triangle with C at top

No rearrangement
Term
Oxidation to vicinal diols
Definition
OsO4/H2O2

Syn
No rearrangement
Term
Ozonolysis Reduction
Definition
Splits molecule in half down center of =
Adds O to each =
H remains
Term
Ozonolysis Oxidation
Definition
Splits molecule in half down center of =
Adds O to each =
H becomes an OH
Term
Regioselectivity Cl2
Definition
speeds = 5, 4, 1
Term
Regioselectivity Br2
Definition
speeds = 2000, 100, 1
Term
Constitutional Isomers
Definition
Same molecular formula, different connectivity
Term
Configurational Isomers
Definition
Can't convert between without breaking a bond

Cis, trans
E and Z
Term
Conformational Isomers
Definition
Convert by a single bond
Term
Stereoisomers
Definition
same constitution, different spacial arrangement
Term
Chiral
Definition
center with 4 different substituents attached
Term
Enantiomer
Definition
Non-superimposable, mirror image
Term
Diastereomer
Definition
Non-superimposable, non-mirror image
Term
Meso Compound
Definition
Molecule with chiral atoms but a plane of symmetry, making the entire molecule achiral
Term
Dextrorotary
Definition
Clockwise rotation
Term
Levorotatory
Definition
Counterclockwise
Term
Optically Inactive
Definition
When a molecule can't be super imposed on it's mirror image
Term
Alkyne Hydrohalogenation
Definition
triple bond
HX
pi complex, double bond
HX
single bond

Markovnikov
Anti addition
No rearrangment
Term
Alkyne Halogenation
Definition
triple bond
XX'
carbocation, double bond
XX'
single bond

Markovnikov
Anti addition
No rearrangment
Term
Tautomerization
Definition
double bond is located next to an alcohol
double bond moves to O, H moves the C
Term
Alkyne Hydroboration/Oxidation
Definition
Terminal: aldehyde
Internal: ketone

triple bond
BH3,THF/OH,H2O2,H2O
ketone or aldehyde

Markovnikov
No rearrangement
Term
Alkyne Hydrogenation Using Pt or Pd
Definition
Produces an alkane
Term
Alkyne Hydrogenation Using Lindlar's Catalyst
Definition
Produces an alkene
Term
Reduction to Trans Alkenes
Definition
Na or K/NH3(I)

Produces Alkene
Term
Acetylide Anion as a Neucleophile
Definition
triple bond with R and H
NaNH2/R'-LG
triple bond with R and R'
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