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Chem 131 Final Exam
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20
Organic Chemistry
Undergraduate 2
03/09/2011

Additional Organic Chemistry Flashcards

 


 

Cards

Term
4 types of amino acids
Definition
1) hydrocarbon non polar
2) acidic
3) basic
4) polar, not charged
Term
How to prep an amino acid
Definition
1) Protein and water takes 7 years

2) protein + 6NHCl, 12hrs, 100degreesC

3) bromination to a CA then amination (won't work on kerosene)
1) Br2 Pbr3 2)H2O
then NH4OH

4) from a alpha CA
NH3
then 1)NaBH4 2)H2O

5) from a malonate
1) alpha halogenate malonate
2) Gabriel amine synthesis
3) alpha-alkylation
4) hydrolysis/decarboxylation

6)strecker synthesis
1) aldehyde + NH3 + CN-
2) H3O+
Term
Amide Bond Formation
Definition
1) CA + SOCl2
2) 2 eq. RNH2 OR 1 eq. RNH2 1 eq. ET3N

each AA has nuc and elec so you block reactivity, protect the amine group (nuc) and protect the carbonyl (elec), then the other ends will react, ET3N, then deprotect
Term
Protecting groups
Definition
For CA: Ph-CH2-OH and acid, go back neutrally with H2 Pd/C or acidic with H+

For CA: Bn

For Amine: t-Boc, has a carbonyl group next to it to ensure that N's lone pairs are not active, break with TFA

For Amine: Ac2O, Et3N
Term
TFA vs Acetic Acid
Definition
TFA is more acidic
Term
[image]
Definition
Kerosene
Term
[image]
Definition
Valine
Term
[image]
Definition
TFA
Term
[image]
Definition
proline
Term
[image]
Definition
Malonate
Term
[image]
Definition
Methionine
Term
How do you cleave methionine?
Definition
BrCN
Term
What will tripsin do?
Definition
cleave after lys (k) and arg (r)
Term
what will chymotripsin do?
Definition
cleave after F, Y, W, anything aromatic
Term
How to make the OH on the CA a better leaving group?
Definition
Method 1: SOCl2
Method 2: DCC
Term
Yield math
Definition
90%= dipeptide
(.9)^2 =tripeptide
(.9)^49=50mer
Term
Deprotonate -NH3?
Definition
spider N thing
Term
Amide bond breaking
Definition
Edman, Cyanogen Bromide, enzymes, bN HCl thing
Term
bN HCl?
Definition
with 100degrees changes protein to amino acid

can change the NH2 by a carbonyl to OH and the NH2 free standing to NH3+
Term
Kinetic vs Thermodynamic product?
Definition
S in ring is kinetic while N is thermodynamic because of the valence electrons of N are closer to the nucleus, tighter and strong bond made
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