1. Determine a sequence of reactions that will convert pentan-3-ol and cyclopentanol into (1- ethylpropoxy)cyclopentane and produce no other ethers. Show all reagents and all synthetic
intermediates.
2. Oxetane is the four-membered ring equivalent of an epoxide. It also reacts with Grignard reagents. Complete the product and draw a mechanism for this reaction.
3. Tetrahydrofuran does not undergo Grignard reaction, and in fact is an excellent solvent for Grignard reagents. Explain why it does not react but oxetane and epoxide do. O MgCl1.
2. H2 O, HCl C 7 H 16 O
O
tetrahydrofuran, THF
