1. List the following compounds in order of increasing boiling point: butanal, 2-butanone, butyl alcohol, and diethyl ether. Explain the molecular bias of this order.

2. Write balanced equation for the oxidation of tolualdehyde with CrO3.

3. Write stepwise mechanism to illustrate the Crossed aldol condensation of benzaldehyde and acetaldehyde.

4. Distinguish between the following pairs by simple chemical tests. Tell what you would do and see.

a. Pentanal and 2-pentanone

b. 2-pentanone and 3-pentanone

c. Pentanal and 1-pentanol

5. How would you distinguish between the following pairs by use of infrared spectroscopy only? Tell what absorption would be present or absent in each case.

a. 2-pentanone and 2-pentanol

b. Acetophenone and p-tolualdehyde

c. 3-pentanone and benzophenone

6. How would you distinguish between pairs in question 5 (above) using only proton NMR spectroscopy? Sketch possible spectrum for each.