Question

1. An epoxide contains a three-atom, cyclic ether as a functional group. The simplest epoxide is: ethylene oxide What makes epoxides useful is their reactivity due to ring strain, coupled with the electron-drawing property of the oxygen. This makes the carbons attached to the oxygen subject to a Sn2 nucleophilic attack. This is followed by a proton transfer step. Fill in the missing products for the following spider diagram (reaction map). You should already be familiar with the nucleophiles used as reagents. The first one is done for you with the nucleophile color coded to help you figure out the pattern. NaCN NaOCH3 NaSH NaOH HCI HOCH H) H20 [H] НО. OCH

Answer 1

NC OCHZ HO Cyanide nucleophile attacks the epoxide in Sn2 mechanism to give the product. Methoxy nucleophile attacks in Sy2 fashion to give the product. NaCN NaOCH3 OH SH HO HO NaSH NaOH Sulfhydryl (HS) nucleophile attacks in Sn2 mechanism to give the product. X- Sn2 reaction of epoxide with hydroxide nucleophile yields the product. HO H2O [ht] CH3OH Protonation of epoxide O followed by attack of chloride nucleophile gives the product HO Protonation of epoxide O followed by the attack of water nucleophile gives the product.