Ester structure and grignard reagent reaction?
An ester and 2 equivalents of a Grignard reagent reacted to form 3-ethyl-3-pentanol and 1-cyclohexyl-1-ethanol after acid workup.
I need the structure of the ester. I the Grignard reagent is :CH3CH2MgBr. I have no idea how to get the ester structure!
- David MLv 61 decade agoFavorite Answer
To elaborate on the 1st answerer, the product is 1-Cyclohexyl-1-Ethyl propionate, which has the following structure...
The way I derived the answer is by looking at the products given and seeing which one had two identical groups added to it since 2 eq of grignard reagent was used. 3-ethyl-3-pentanol has 3 ethyl groups, therefore, it was originally the part of the molecule that contained the ester carbonyl carbon (since two ethyl groups added to it). Therefore, the original ester had to have the following structure...
...where the R group = 1-cyclohexyl-1-ethanol since it was the leaving group after the addition of the 1st equivalent of grignard reagent...
Hope this helps!!!
- Mark RLv 51 decade ago