Answer to Question #187965 in Organic Chemistry for Geovani Clarke

Question

1.     Using 1-butene as the only organic starting material, outline how each of the following compounds might be synthesized from it, stating clearly the reaction conditions in each case.                         

a.      2-butanol

b.     2-butanone

c.      Butane

d.     1,2-Dichlorobutane

 

Answer 1

Two sets of reagents are required to convert butanone into 2-butene. First, we use to reduce the butanone into a 2-butanol. Second, we use heat and acid to dehydrate the butanol and yield the final desired product.

You could either use oxymercuration((1) HgOAc2, H2O 2)NaBH4) or hydroboration(BH3/THF/NaOH/H2O to put an OH on carbons 2 or 3, then oxidize using either a weak or strong oxidizing agent. The reason that either would work is because the OH is a second degree so it can only be oxidized to a ketone.

The method of obtaining 1-butene consists of the isomerization in BBF of 1-butene into 2-butenes, removal of isobutane, isobutene and 1,3- butadiene from the 2-butenes by effective rectification and then reverse isomerization of 2-butenes into the 1-butene with the separation of the latter by rectification.