1a. When sodium benzyloxide is reacted with excess acetic anhydride it produces benzyl acetate and byproducts. What are those byproducts? If extracting with dichloromethane, what could be added to the aqueous layer to sequester the byproducts? Which layer would be on top, the aqueous layer or organic layer?
1b. When sodium benzyloxide is reacted with excess acetyl chloride it produces benzyl acetate and byproducts. What are those byproducts? If extracting with chloroform, what could be added to the aqueous layer to sequester the byproducts? Which layer would be on top, the aqueous layer or organic layer?
To determine the possible byproducts in both reactions, we need to consider the reactants and the reaction conditions.
1a. When sodium benzyloxide reacts with excess acetic anhydride, benzyl acetate is the desired product. However, byproducts can be formed due to side reactions. Some potential byproducts could include acetic acid, benzoic acid, and unreacted starting materials.
To sequester or remove the byproducts from the aqueous layer during extraction with dichloromethane, one option is to add a basic aqueous solution. Sodium bicarbonate (NaHCO3) or sodium hydroxide (NaOH) can be added to neutralize the acidic byproducts, forming water-soluble salts that can be extracted into the aqueous layer. These salts can then be easily separated from the organic layer.
In the extraction process, the organic layer, which contains the desired benzyl acetate and any organic solvent used (in this case, dichloromethane), would be on top, while the sequestering agent-treated aqueous layer would be below.
1b. When sodium benzyloxide reacts with excess acetyl chloride, again, benzyl acetate is the desired product. However, byproducts can also form in this reaction. Potential byproducts could include acetyl benzoate, acetyl chloride, and unreacted starting materials.
To sequester the byproducts during extraction with chloroform, a basic aqueous solution can also be added to the aqueous layer. Sodium bicarbonate or sodium hydroxide can be used to neutralize the acidic byproducts, forming water-soluble salts that can be extracted into the aqueous layer. These salts can then be separated.
Similarly, in this extraction, the organic layer (containing benzyl acetate and chloroform) would be on top, while the aqueous layer treated with the sequestering agent would be below.
It is important to note that the mentioned byproducts are potential ones, and the exact byproducts formed may depend on various factors such as reaction conditions, catalysts used, temperature, and time. Experimental analysis and characterization techniques are typically employed to identify specific byproducts.