Question

Propyl Benzhydryl Ether (continued on next page):

Answer 1

Answer:

See detailed explanation and image attached

Explanation:

1 mole of 1-pentanol reacts with 1 mole of benzhydrol

Number of moles in 1.5 g of benzhydrol = mass/molar mass = 1.5 g/184 g/mol = 0.008 moles of benzhydrol

x moles of 1-pentanol reacts with 0.008 moles of benzhydrol

x = 0.008 moles of 1-pentanol

If 1 mole occupies 22.4 L

0.008 moles occupies 22.4 * 0.008 moles = 0.179 L of 1-pentanol is required.

The mechanism of the formation of n-pentyl benzhydryl ether involves the protonation of the -OH group in benzhydrol. This is followed by loss of water molecule creating a carbocation which is attacked by the 1-pentanol.  Abstraction of a proton by a base completes the mechanism, regenerates the acid and yields the n-pentyl benzhydryl ether as shown in the image attached.

The synthesis of diethyl ether occurs by protonation of one ethanol molecule followed by SN2 attack by anothe ethanol molecule and a simultaneous loss of a water molecule. Deprotonation by a base yields the  diethyl ether