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Organic : Aldol Condensation
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 Message 1 of 4 in Discussion 
From: MSN Nicknamewhat464  (Original Message)Sent: 4/19/2008 1:25 AM
A mixture of Compound A to react with Compound B in the presence of ethanolic potassium hydroxide. After appropriate workup, he obtained the desired and expected organic product, Compound C.
After H1/C13-NMR / IR analysis of Compound A and B, I determined:
Compound A- 3,5-dimethoxybenzaldehyde
Compound B- 4'-butoxyacetophenone
Can you tell what the product (Compound C) is when Compound A and Compound B reacts in presence of ethanolic potassium hydroxide?


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 Message 2 of 4 in Discussion 
From: MSN Nickname·Steve·Sent: 4/19/2008 2:10 AM
4-butoxyacetophenone has α-hydrogens that will react with the base, KOH, forming the enolate ion which can then react with the carbonyl carbon of 3,5-dimethoxybenzaldehyde in aldol fashion.
 
Steve

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 Message 3 of 4 in Discussion 
From: MSN Nicknamewhat464Sent: 4/19/2008 2:38 AM
Can you show me the structure of Compound C? Thanks

Reply
 Message 4 of 4 in Discussion 
From: MSN Nickname·Steve·Sent: 4/19/2008 4:48 AM
For the structure of the product of the condensation of benzaldehyde and acetophenone, see the brief Wikipedia article on chalcone:
http://en.wikipedia.org/wiki/Chalcone
 
After the aldol condensation, elimination of water has occurred to give a highly conjugated, α,β-unsaturated ketone.
 
Steve

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