In this lab we were performing williamson ether synthesis to turn Acetominophen

Question

In this lab we were performing williamson ether synthesis to turn Acetominophen into Phenacetin (through addition of anhydrous K2CO3, 2butanone, and ethyl iodide

a) Your lab ran out of ethyl iodide. Your TA suggests that you carry out the alkylation of acetominophen with allyl bromide, using the same K2CO3 in 2-butanone reaction conditions. Is this a good suggestion? Explain.

(iv) Your friendly chemistry professor designs a preparation of tubacetin (4acetamidophenyl tbutyl ether).  The procedure is completely different.  It employs 2methylpropene and H2SO4 as a catalyst in chloroform.  Will the preparation work?  Explain your reasoning.

Explanation / Answer

well you can use allyl bromide if ethyl chloride is not available in the lab... in this case our % yield will be lower if the allyl bromide runs down the side of the condenser. so, please make sure that it should fall directly to reaction mixture. well it is a good suggestion if C2h5Cl is out of stock.

Well this prepation will works only in mild condition, since it is acid catalysed reaction we should be very careful while monitering the reaction. better would be if you can provide starting material or precursors for the synthesis of tubacetin (4acetamidophenyl tbutyl ether) or better to search the literature.( I have searched but not much work has been done in this area i.e direct prepartion of tubacetin)

Thanks

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