Propyl Benzhydryl Ether (continued on next page): (1) What volume of 1-pentanol is needed to convert 1.50 grams of benzhydrol to n-pentyl benzhydryl ether?
(2) Based on the results of this experiment, write a mechanism for the acid catalyzed reaction of benzhydrol with 1-pentanol to give the product from the last question. (Note: the mechanism is written on the first page of this experiment. You just have to figure out, based on the experimental results, which alcohol is ROH and which is R'OH and the write it using those two alcohols.)
(3) Under milder temperatures than what is needed for dehydration, strong acids catalyze the self-condensation of 1-propyl alcohol to give di-n-propyl ether. The mechanism differs from that of today's reaction in that the protonated alcohol undergoes an Sy2 rather than an Syl reaction. Write the mechanism for the acid catalyzed condensation of ethyl alcohol to give diethyl ether. Note: make sure your mechanism has the following three steps (a) protonation (b) Sx2 (not Syl) and finally (c) deprotonation.