Aldol Condestion/Enolate Question

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Claritynow

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I was reviewing this question and didn't see the answer on here so I decided to make a thread about it. Any help would be appreciated.

1)I read that when Acetaldehyde is treated with a catalytic amount of base the enolate ion is produced. It this because the acetaldehyde loses the acidic proton because it is in acidic conditions(similar to Amino acids acting like a base in acidic pH conditions)?

2)Also when the acidic proton departs in the formation of the enolate why is the charge on the alpha Carbon negative. Wouldn't it be positive since in essence it has lost a bond and will receive resonance stabilization and the Oxygen will then take a negative charge?

I may be seeing things in correctly so any help would be appreciated. thank you in advance!

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I was reviewing this question and didn't see the answer on here so I decided to make a thread about it. Any help would be appreciated.

1)I read that when Acetaldehyde is treated with a catalytic amount of base the enolate ion is produced. It this because the acetaldehyde loses the acidic proton because it is in acidic conditions(similar to Amino acids acting like a base in acidic pH conditions)?

It loses the proton because it is in basic conditions as you said above.

2)Also when the acidic proton departs in the formation of the enolate why is the charge on the alpha Carbon negative. Wouldn't it be positive since in essence it has lost a bond and will receive resonance stabilization and the Oxygen will then take a negative charge?

When H+ disassociates from the alpha carbon, the alpha carbon retains the electron that originally belonged to the hydrogen, leaving behind a negative charge. It does undergo tautomerization in which the negative charge is displaced onto the oxygen atom and double bond forms between the alpha carbon and the carbonyl carbon. However, carbon never has a positive charge.

I may be seeing things in correctly so any help would be appreciated. thank you in advance!

See bold above.
 
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