Q1: a) Arrange the compounds in order of decreasing pKa, highest first. ОН ΟΗ ῸΗ дон ОН ОН CI Br

(4 pts - 2 pts each part) A route that can be taken to prepare a hydrophobic (water-repellent) aerogel is to start with trichloromethylsilane, CH3SiCl3 as the silicon source. a. What is the chemical reaction that this undergoes to form a product with Si-OH groups? Write as complete of a chemical equation as you can. CI CI-SI-CH3 CI b. The formation of a byproduct is what drives this reaction - what is the byproduct (if you didn't already answer it in part (a)) and how/why does it form?

b) Circle the substrate that would not efficiently generate a Grignard reagent upon reaction with Mg in ether. CI Br ד c) Circle the Grignard reagents that contain incompatible functional groups. MgBr HO MgBr MgBr MgBr MgBr HO MgBr