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In the oxidation of cyclododecanol to cyclododecanone. In the work up step, after I added diethyl ether and then separated the two layers, organic and aqueous.

Then I added diethyl ether again, shake, then separate the two layers. I combined two organic layers together but accidentally forget to add sodium bicarbonate before adding diethyl ether the third time.

After I separated the organic and aqueous layers, I added the sodium bicarbonate in the organic layer.

Is that the reason why my percent yield is so low and why?

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closed as unclear what you're asking by Klaus Warzecha, Ben Norris, Satwik Pasani, tschoppi, LievenB Mar 11 at 17:41

Please clarify your specific problem or add additional details to highlight exactly what you need. As it's currently written, it’s hard to tell exactly what you're asking. See the How to Ask page for help clarifying this question.If this question can be reworded to fit the rules in the help center, please edit the question.

Maybe your question could also include some details on the protocol that was followed (type of oxidizing agent used, was sodium bicarbonate added as a solution or powder, how you recover/purify your reaction product...) –  PLD Jan 20 '13 at 21:35
Could you please state what the components of the separated layers at each step could be ? –  Aditya Sriram Jan 23 '13 at 2:48
Could you also state what your yield was, and what the literature yield is? That would make it easier to judge where the error might lie. –  Tanith Rosenbaum Jan 23 '13 at 15:25