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Nucleophilic addition to the carbonyl
The C=O bond is polarized: oxygen pulls density, so the carbon carries a partial positive chargeAsk Sendy and welcomes nucleophiles.
Nu− + R2C=O → R2C(O−)Nu → R2C(OH)Nu
Aldehydes react faster than ketones. Less steric bulk at the carbon, and only one alkyl group pushing electrons in.
Recall Why does hydration favour formaldehyde over acetone?
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Card 7 of 24Unit 4: Carbonyls
Why are aldehydes more electrophilic than ketones?tap to flip
One alkyl group instead of two: less electron donation into the carbonyl and less steric crowding at the carbon.
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Slide 9 of 14Hemiacetal formation
Alcohol attacks the carbonyl carbon
Proton transfer gives the hemiacetal
Acid catalysis speeds the second addition
MayaTheo
12:4031:05
Theo: So the alcohol is the nucleophile this time, and the carbonyl carbon is still the one taking the hit.
Ask Sendyknows all 3 classes
Which units in Orgo and Biochem both cover enzyme catalysis? I have both exams next week.
Two overlaps. Orgo Unit 4 covers acid-catalysed carbonyl addition, and Biochem Unit 3 reuses the same mechanism for serine proteases.
Study them together: the tetrahedral intermediate shows up in both.
Open Orgo Unit 4 notesPractice test, both units
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