Aldols Flashcards
Base Catalyzed aldol condensation
Carrying out what helps to ensure the formation of the intended product in cross-aldol condensations involving a ketone and an aldehyde?
using bulky base such as LDA will strongly favor removing hydrogens from the alpha-carbon that is the least sterically hindered. This favors the intended product instead of a mixture. With a non-bulky base, we cannot control which alpha carbons will have their hydrogens removed.
Reaction is which two molecules of either ketones or aldehydes condense via nucleophillic attack
Aldol condensation
What are the basic components of a robinson annulation?
Michael addition followed by aldol condensation
What is the industrial relavence of robinson annulation?
It can help make steroid hormones
What is the following reaction called?
Michael addition
What are the basic components of a michael addition reaction?
An enolate attacks a beta carbon on an alpha beta destaurated ketone.
How does the acid catalyst increase the rate of reaction in the following?
It increases the electrophilicity of the carbonyl carbon.
As evident from an early step in the reaction mechanism, an H+ ion protonates the carbonyl oxygen. This protonation makes the carbon-oxygen double bond significantly weaker, allowing the carbonyl carbon to become even more electrophilic (or partially positive) than before. This facilitates the reaction by increasing the chance that the nucleophilic enol will attack.
What is the product of a michael addition?
1,5 dicarbonyl
What tends to be the products of a robinson annulation?
Alpha beta unsaturated ketone, a six ememebred ring