[johnj321]

.

[orgopete]

If the acetate ester were treated with methoxide, what would happen?

[johnj321]

Would the methoxide attack both of the electrophilic carbons? I still dont see how that would replace the ester group on the end with an OH

[Mitch]

The product is symmetric, how much of the methoxide would you have to react to get to the product?

[johnj321]

I figured it out, thank you for responses.

[Mitch]

please don't delete your questions. Many people will use your question to learn from.

[orgopete]

The starting material was not symmetric, it was CH3OOCCH2CH2CH2OOCCH3, the acetate of methyl 4-hydroxybutanoate. Methoxide would attack each carbonyl. Loss of methoxide from the methyl ester will return a methyl ester. Attack of the acetate carbonyl would give methoxide or the alkoxide of the desired product. With a large amount of alcohol, methoxide would give the desired product through ester exchange.