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Organic Chem 3120
Cramier
28
Chemistry
Undergraduate 3
09/26/2011

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Term
Calculating degrees of un-saturation
Definition
Compare fully saturated molecule to current with the following formula
#H+(1)#Halogens-(1)#N or S and (0) for Oxy
Term
Cis / Trans isomerism
Definition
  • all terminal alkenes i.e. those with a C=CH2 unit do not exist as cis- and trans- isomers.
  • all 1,1-symmetrically disubstituted alkenes i.e. those with a C=CR2 unit do not exist as cis- and trans- isomers.
  • alkenes with the R-CH=CH-R unit can exist as cis- and trans- isomers.
Term
[image]
Definition

Can Exist if R1 is not = to R2

and

R3 is not = to R4

Term
[image]
Definition
Trans Isomer
Term
[image]
Definition
Cis-Isomer
Term
Cahn-Ingold-Prelog priority rules
Definition

Rule 1) Rank the first atom according to atomic # w/ prioity based on higher number.

Rule 2) Continue to move away from the first until a difference is found.

Rule 3) Multiple bonds are counted as two or three bonds to single atoms

Term

Zusammen Isomerism

(Z)

Definition
The prioroity groups are on the same side.
Term

Entgegen Isomerism

(E)

Definition
Priority groups on opposite sides
Term
Markovnikov's Rule
Definition
H will attach to the carbon with the fewest alkyl substituents and the X attaches to the carbon with the most alkyl sudstituents
Term
Carbocation Stability-Rank Highest to lowest!
Definition
1) Tertiary
2) Secondary
3) Primary
4) Methyl
Term
Hammond Postulate
Definition
The intermediate most closely resembles either the reactants or products depending which is ever is highest energy
Term
Zaitsev's Rule
Definition
The preferred product is the more highly substituted product therefore the more stable
Term
Hoffman product
Definition
anti-Zaitsev's Rule is the dominate or major product
Term
Two most common elimination reactions to make a Alkene?
Definition
1) dehydrohalogenation
2) dehydration
Term
Dehydrohalogenation of a Alkyl
Definition
Removal of a halogen and hydrogen with a strong base from a alkyl halide.

KOH + CH3CH2OH (ethanol)
Term
Dehydration of a Alkyl
Definition
Removal of a water molecule of an alkyl alcohol with a strong acid.

H2SO4, H2O, THF
Term
Halogenation of a Alkene
Definition
Yeilds 1,2-dihalides

Only Br or Cl used
Term
Halogenation yields Cis or Trans?
Definition
Yields only Trans
Term
Halohydrin reactions
Definition
Add HO-Cl or HO-Br to the Alkene

reacts like halogenation and forms trans only

NBS and (DMSO) and H2O
Term
Oxymercuration
Definition
The addition of H2O to a alkene (hydration)

Hg(OAc)2 + H2O + NaBH4
Term
Hydration
Definition
Adding H2O to a alkene
Term
Oxymercuration follows Markovnikov's Rule or not?
Definition
Follows Markonikov's Rule
Term
Hydroboration
Definition
The addition of H2O with BH3 in a THF solvent.
Term
Hydroboration follows Markovnikov's Rule or not?
Definition
non-Markovnikov addition because of steric crowding.
Term
Hydrogenation
Definition
Adds H to alkenes with the use of metals like Pd or Pt
Term
Reduction?
Definition
Forming C-H or breaking C-O, C-N, C-X
Term
Oxidation
Definition
The loss of electron density by carbon

Forming C-O, C-N, C-X or breaking C-H
Term
Epoxidation
Definition
The adding of three membered ring containing Oxygen

Treatment with a Acid creates a 1,2-diol
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