L14 - Electrophilic Carbonyls 1
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What are the steps of reactions of carbonyls with H2O?
• LP on O attacks C in C=O • e- moves to O (O-) • proton transfer = hydrate (minor)
How to determine which one is the major or minor product:
The closer the actual angle is to the wanted angle
What are the steps in reactions of carbonyls with R-OH?
• LP on O attack C in C=O (Cat HA) • loss of H+ • addition of H+ • R-OH reacts again = product with 2ROs (4 species)
What is the na,e of the product if R1 is an alkyl?
Hemiketal
What is the name of the product if R1 is an H?
Hemiacetal
What happens when there is an OH in the same chain as the carbonyl?
Forms a ring cyclic hemi acetal - LP on OH attacks C on C=O - e- moves to O, breaks db
What are the steps in reactions of carbonyls with amines?
• LP on N attack C on C=O • e- move to O (O-) • proton transfer = hemi aminal • addition of H+ (Cat HA) • LP ON N forms db • e- moves to H2O (kicked out) • loss of H+ = imine
What is the name of a positive imine?
Iminium (keto)
What is the name of an imine with another db?
Enamine (enol)