What reaction would be best for preparing 2-isopropoxy pentane in high yield?

A student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.

In the workup of the grignard reaction of turning bromobenzene to benzoic acid, we start by mixing the grignard with HCl and diethyl ether. We discard the aqueous layer and wash the organic layer with water. Then, the organic layer is extracted with NaOH. Then, the extracts are heated to remove ether. Then, it is precipitated with HCl. Precipitate collected. Let it dry and finally, purified with toluene and hexanes. Please make a flowchart of the process of this workup indicating what products and byproducts are forming. And what compounds are in the aqueous layer and organic layer in the steps.

For the reaction shown below, 582 mg of 4-chlorophenol, 798 mg of benzyl bromide, and excess sodium hydroxide are used to obtain 847 mg of 4-chlorophenyl benzyl ether. What is the percent yield of 4-chlorophenyl benzyl ether? 4-chlorophenol MW = 129 g/mol; benzyl bromide MW = 171 g/mol; sodium hydroxide MW = 40.0 g/mol; 4-chlorophenyl benzyl ether MW = 219 g/mol