Chemistry
Workshops
Chapter 10 Workshop Problems
First Term Review & Alkyne Reactions
1. The following was part of the last workshop from fall term. Recreate and improve on the chart that you made last term.
The four families of compounds studied in the first term were the alkanes, alkenes, alkyl halides, and alcohols. Represent them by four circles and write arrows that show reactions that convert a compound from one family to another. Include all other reactions that we have studied; if they don't lead to one of these functional groups, just show them emanating from one of the circles.
2. Make lists showing as many examples as you know of reactions that:
a. form new carbon-carbon bonds
b. have a specific stereochemistry
c. involve free radical intermediates
d. involve carbocation intermediates
e. involve oxidation of an organic molecule
f. involve reduction of an organic molecule
3. Show how to efficiently carry out the following synthetic
transformations, specifying reagents and reaction conditions.
Each transformation requires at least two steps.
Tactics for conquering synthetic problems:
a. What could be the penultimate (next to last) compound in the synthetic sequence?
b. How could you convert the penultimate compound to the ultimate compound?
c. If you cannot answer (b), then recycle to (a) and try another penultimate compound.
d. When you get a good final step, then figure out how to make the penultimate compound, following the same logic until you work back to the starting material.
