Which of the following synthesis methods would you use to prepare a symmetric ether with the molecular formula C4H10O: A) Williamson ether synthesis using sodium hydride and 1-bromobutaneB) Acid-catalyzed dehydration of 2-butanolC) Nucleophilic substitution of 1-chlorobutane with sodium ethoxideD) Ring-opening of an epoxide with ethylamineExplain your reasoning for choosing the method and provide the chemical equation for the reaction.

Question

Which of the following synthesis methods would you use to prepare a symmetric ether with the molecular formula C4H10O: A) Williamson ether synthesis using sodium hydride and 1-bromobutaneB) Acid-catalyzed dehydration of 2-butanolC) Nucleophilic substitution of 1-chlorobutane with sodium ethoxideD) Ring-opening of an epoxide with ethylamineExplain your reasoning for choosing the method and provide the chemical equation

Answer 1

I would choose option C  Nucleophilic substitution of 1-chlorobutane with sodium ethoxide to prepare a symmetric ether with the molecular formula C4H10O.Reasoning:A symmetric ether has the same alkyl groups on both sides of the oxygen atom. In this case, the ether would be diethyl ether  C2H5-O-C2H5 . A  Williamson ether synthesis using sodium hydride and 1-bromobutane would result in the formation of an unsymmetrical ether, butoxybutane  C4H9-O-C4H9 , which does not meet the requirement of a symmetric ether.B  Acid-catalyzed dehydration of 2-butanol would result in the formation of an alkene  1-butene or 2-butene  rather than an ether.D  Ring-opening of an epoxide with ethylamine would result in the formation of an amino alcohol, not an ether.Chemical equation for option C:1-chlorobutane  C4H9Cl  + sodium ethoxide  C2H5ONa  -> diethyl ether  C2H5-O-C2H5  + sodium chloride  NaCl