1) Show the steps and reagents necessary to prepare the following compound.

Use retrosynthetic analysis as a tool to guide your synthesis. (20 points)

2) The pKa of cyclopentadiene is found to be 16 while, by contrast, that of

cycloheptatriene is found to be 36. Explain the large difference found in the
two pKa values. Show drawings, if necessary and do not use more than 50 words.
(15 points)

3) Suggest a reasonable synthetic strategy for the synthesis of 3,5-dinitrobenzyl

alcohol from benzaldehyde. (15 Points)

4) Complete the following reaction sequence, giving structural details of all

significant intermediates and the final product. (15 points)

5) Draw the full mechanism of formation of Butanoyl Chloride via using of

thionyl chloride and appropriate carboxylic acid. (25 points)