Carbonyl Chemistry Flashcards
What is a nucleophile? Give examples.
Electron donator e.g. OH-, CN-, NH3+, H2O
What is an electrophile? Give examples.
Electron acceptor e.g. H3O+ (hydronium ion), AlCl3, BF3 (boron trifluoride), halogen molecules (incomplete shell)
What is the most important mechanism in carbonyl chemistry? Describe briefly.
Alpha substitution by nucleophilic attack
Occurs at position next to carbonyl group (the alpha carbon).
Would presence of acid/base have any effect on carbonyls?
Yes - equilibrium reaction could take place.
What type of bonding is present in carbonyls?
Alpha-carbon takes part in a pi bond, which can act as a nucleophile
Is the alpha hydrogen basic or acidic?
It is relatively acidic as it can form enols or enolates - it can act as a nucleophile
What could happen after nucleophilic attack? (3 options)
Option A: the reaction reverses (double bond reforms and nucleophile is ejected)
Option B: Substitution (best leaving group is substituted for the nucleophile)
Option C: Addition - there is no leaving group so addition takes place in presence of water forming a tetrahedral
What is the most reactive carbonyl?
Acyl chloride - would never be found in a drug - too reactive
Least reactive carbonyl?
Amides - make up proteins that do not dissolve in water
Name different types of carbonyls (7)
Acid chloride Anhydrides Acids Esters Amides Ketones Aldehydes
What happens in salt/vinegar reaction?
The salt is ejected (Cl-)
How is ethanol (drinking alcohol) processed in the body?
HINT: ADME
It is metabolised AND excreted
Metabolised - oxidised using alcohol dehydrogenase in the liver
What is the toxic intermediate from alcohol metabolism?
Why is it dangerous?
How is it managed in the body normally?
Acetaldehyde
It can damage DNA - prevents body repairing damage. Damaged DNA can grow and cause a tumour.
It is oxidised further by aldehyde dehydrogenase to give ethanoic acid (harmless but is fatty)
What causes alcohol poisoning?
How can it be treated?
Alcohols related to ethanol e.g. methanol or ethelene glycol
They are oxidised to an aldehyde which cannot be oxidised further
Can be treated with whiskey (alcohol) which is processed in place of the existing/dangerous alcohol molecules.
What is the Grignard reagent?
R-MgBr
