Draw eugenol as a line structure. The double bonds of the benzene ring are fairly unreactive unless you use special catalysts. But the double bond on the side group is reactive. Draw the mechanism of eugenol reacting with HBr to form the two possible carbocation intermediates. Put your intermediates into square brackets. Label each carbocation as a methyl carbon or 1°, 2°, or 3°. Then circle a more stable carbocation if one is more stable. Can you guess what the final product is?

4. A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in his radiator this winter. He proposes the following reaction to his instructor, who quickly explains that this reaction won't work as proposed due to the student's choice of reagent. 1) NaH 2) H20 OH Но a) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above? b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give the desired ethylene glycol product.

What is the missing reactant in this organic reaction? i NH2 +R + H2O Specifically, in the drawing area below draw the skeletal ("line") structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. Note for advanced students: you may assume no products other than those shown above are formed.

Draw the starting reactant that would produce this alcohol when treated with this reagent. Ignore inorganic byproducts. Drawing 1. PhLi 2. H3O+ HOH