Question

Construct an efficient three-step synthesis of 1,2-epoxycyclopentane from bromocyclopentane by dragging the appropriate formulas into the bins. Note that each bin will hold only one item, and not all of the given reagents or structures will be used.

Answer 1

Br Reagent 1 LE2 Mech.) (CH3)3C XH + Br2H20 → Product 1 Product 2 Br Reagent 3 +NaOH 1,2-epoxycyclopentane

Answer 2

Synthesis of 1,2-epoxycyclopentane from bromocyclopentane:

Step 1: The reactant is an alkyl halide, which undergoes substitution and elimination by adding the reagent potassium tertiarybutoxide is a strong non nucleophilic base.

                      

Step 2: The product of step 1is an alkene, which undergoes addition reaction to its pi bond. The reagent Br₂+H₂O serves as the source of the electrophile Br⁺ resulting addition in addition of Br and OH to the double bond.

            

                     

Step 3: When the base sodium hydroxide added to the product in the step 2(halo hydrin), it deprotonates the alcohol forming alkoxide. Next, the alkoxide nuclephile attack the electrophilic carbon by S_N2 mechanism.

                    

Answer 3

(CH3)3CO-K+ Br NaoH