Conjugate addition Flashcards
cross- condensation reactions
Does this reaction work?
If not then why?
It doesn’t work
The ketone is very hindered and very conjugated. It is less electrophilic than a normal ketone. And normal ketones are less electrophilic than aldehydes. So, the aldehyde will just react with itself
For crossed aldol reactions to work cell, what two conditions must be met?
- One partner must capable of enolization
- The other partner must be incapable of enolization and be more electrophilic than the enolizable partner
Retro aldol reaction
Name 2 anticancer enone drugs that target DNA polymerase?
What is key for this actitivty to happen?
Michael addition is the key for this activity
Where are carbonyl compounds electrophilic?
Where are Enols nucleophilic?
Where are Enones electrophilic?
Draw the 1,2- addition mechanism between a nucleophile and a ketone
Complete this 1,4- conjugate addition mechanism
What are amines good for, nucleophiles or electrophiles?
What can they react in the absense of?
Amines are good nucleophiles and can react in the absence of acid or base
Complete the mechanism
Whats the mechanism for this reaction
Draw the mechanism of conjugate addition with tertiary amines
Does this reaction work?
If not then why?
- However, the intermediate cannot deprotonate to produce an uncharged product
- The tertiary amine is eliminated, regenerating the starting materials
- The reaction does not work
What is conjugate addition the reverse of?
The E1cb mechanism
Draw the mechanism of alcohol- acid catalysed conjugate addition
between MeOH and pentan-4-ene-2-one
Whats an excellent nucleophile for conjugate addition?
What do thiols require to undergo conjugate addition? Why is this?
Thiols
Inactivation of DNA polymerase by vernolepin
Redox of secondary alcohol?
Reduction of carbonyl containing ketones, esters and aldehydes?
