Chapter 14, Problem 14.32SP

Glycerol (propane-1,2,3-triol) is a viscous syrup with molecular weight 92 g/mol, boiling point 290 °C, and density 1.24 g/mL. Transforming the three hydroxy groups into their trimethylsilyl ethers (using chlorotrimethylsilane and a tertiary amine) produces a liquid that flows easily, has molecular weight 309 g/mol, boiling point approximately 180 °C, and density 0.88 g/mL. Draw the structures of these two compounds, and explain why glycerol has a lower-molecular weight but a much higher boiling point and density.