L15 - Electrophilic Carbonyls 2
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Steps to forming an ester when the carbonyl is very reactive (acyl chloride)
• LP on O attacks C on C=O on OH • e- move to O (O-) • e- move to kick Cl out + loss of proton = ester
Steps to making an ester with a carbonyl that isn’t very reactive (alcohol)
• use Cat HA to add proton • LP on O attacks C on C=O • e- move to O • proton transfer to other OH • LP on O moves to +ve O • loss of proton = ester
Steps to making an amide with a very reactive carbonyl (acyl chloride)
• LP on N attacks C on C=O • e- moves to O (O-) • e- moves to kick Cl out • loss of proton = amide
What forms when an alcohol reacts with amine?
Doesn’t form the amide - forms a salt
How does nature make anide bonds from COOH?
It uses atp - LP on N attacks C on C=O - e- moves to O, moves back to form db - kicks out phosphate group
Steps to the hydrolysis of an ester in acidic conditions
• protenated ester • LP on O (H2O) attacks C=O • e- moves to +ve O • proton transfer • LP on OH moves to kick acl group Reversible
Steps to the hydrolysis of ester in basic conditions
• LP on OH attacks C on C=O • e- moves to O (O-) • e- moves to kick out OR • H in the COOH transfers to OR Not reversible
Steps to the hydrolysis of an amide in acidic conditions
• protenated amide • LP on O (H2O) attacks C on C=O • e- moves to +ve O • proton transfer to NH2 • LP on OH kicks out NH3+ • loss of proton = COOH Not reversible
Steps to the hydrolysis of an amide in basic conditions
• LP on OH attacks C on C=O • e- moves to O • e- moves to kick out NH2 (Slow as poor LG) • COOH • loss of proton