fgc2 Flashcards
What are the simplest carbonyl groups?
The simplest carbonyl groups are: Aldehyde, Ketone, Carboxylic Acid, Ester, Amide.
Why is the carbonyl carbon susceptible to nucleophilic attack?
The oxygen atom in the carbonyl bond is more electronegative than carbon, creating a polarized bond where the carbon is electron-deficient and prone to nucleophilic attack.
What are the two types of reactions carbonyl groups can undergo?
Nucleophilic addition, Electrophilic addition.
What determines the order of addition in carbonyl reactions?
The conditions: Basic conditions: Nucleophile attacks the carbonyl carbon directly. Acidic conditions: The carbonyl oxygen is protonated first, making the carbon more electrophilic.
What happens when an aldehyde reacts with one equivalent of alcohol?
It forms a hemiacetal in a reaction that is usually acid-catalyzed.
Is hemiacetal formation reversible?
Yes, hemiacetal formation is reversible under both acidic and basic conditions.
What are hemiacetals, and why are they important in sugars?
Hemiacetals are intermediates formed by the reaction of an aldehyde with an alcohol. Many natural sugars contain hemiacetals, and their reversible formation is essential for sugar reactivity.
Explain the reactivity of a carbonyl bond with a charged nucleophile.
A charged nucleophile directly attacks the electron-deficient carbonyl carbon.
Explain the reactivity of a carbonyl bond with an uncharged nucleophile.
An uncharged nucleophile typically attacks a protonated carbonyl (acid-activated), as protonation increases the electrophilicity of the carbon.
Why is the reactivity of carbonyl groups important in drug design?
Differences in carbonyl group reactivity affect drug stability and activity, especially during hydrolysis of complex carbonyl-containing drugs.
