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Organic Chemistry Chapt 14
Conjugated compounds and ultraviolet spectroscopy
17
Chemistry
Undergraduate 2
11/22/2011

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Term
What are conjugated compounds?
Definition
 compounds with alternating double and single bonds 
-found in pigments responsible for colors of fruit and flowers 
Term
What do you call conjugated hydrocarbons with many double bonds?
Definition

 

 

Polyenes

(ex. Lycopene)

Term

 

When conjugate alkenes react with HBr, HCl, and so on..the first step is protonation of one of the double bonds to form carbocation and then what is formed...?

Definition

 2 resonance...

1 with positive charge on # 2 carbon

1 with positive charge of # 4 carbon

(1,2 addition and 1,4 addition)

so the ending resulting in somewhere in between

Term
Which addition happends at a temp of 0 degrees celsius? and 40 degrees celius?
Definition

0= 1,2 additions

40= 1,4 additions

Term
What is a kinetic product? which reaction is this the result of?
Definition

this is a 1,2 addition that has lower activation barrier. 

*Cannot return to carbocation intermediate, irreversible

Term
What is a thermodynamic product? 
Definition

Higher temp rxn that is reversible, 

*has enough energy to return to cation and reach equilibrium

*Will aslo favor the lower energy product regardless of hieght of activation barrier

*

Term
What are Diels -alder reactions?
Definition

conjugated diens react with alkene (dienophile/diene lover) to form a six membered ring (hexagon)

 

* 1 step reactions with no intermediates!

Term
Name 3 Good electron-donating groups  to put on dienes(EDG):
Definition

1.)ethers(OR)

2.)Alcohols (OH)

3.)Amines (NR2)

Term
Name 3 Good electron withdrawing groups for dienophiles:
Definition

1.)Cyanogroups (CN)

2.)Nitro Groups (NO2)

3.) Carbonyl Compounds (ester, aldehydes, acids, ketones, and so on..)

Term
What conformation is required for dienes?
Definition

S-Cis conformation...Both double bonds are on the same side of C-C single bond that seperate the two  double bonds bonds


*2 double bonds are in proper orientation to undergo reaction 

Term

[image]

what is this called?

Definition
Dien alder reaction
Term
Dien alder reactions are sterioselective..what does that mean?
Definition

forms one stereoisomer over another...
Start with cis----end with cis product

Start with trans---end with trans product 

Term
What type of additionis used in the polymerization of the growing chain of a conjugated diene monomer?
Definition

 

 

1,4 addition

Term
The initator (In) of a polymerization reaction of dienes can either be...
Definition

 

 

acid or a radical

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