Week 2 Problem set - CONDENSED KEY

1.

2. cyclohexanol [limiting reagent is the reagent that limits the reaction; in this week's experiment cyclohexanol was the only reagent used. H₂SO₄ is a catalysis and thus should not be considered.]

3. What is the expected alkene product formed from the dehydration of the following alcohols? Show major products only.

a. 2-methyl-2-butene

b. 2,3-dimethyl-2-butene

c. two possibilities (either answer is acceptable): 1-methycyclohexene (resulting from a 1,2-hydride shift) or cycloheptene (resulting from a 1,2-carbon shift).

d. 1-methylcyclohexene

e. 1-methylcyclohexene

f 1,2-dimethylcyclopentene (resulting from a 1,2-methyl shift)

g. 1-methylcyclopentene

i.

5. The ring expansion is favored due to less angle strain in the five-membered ring.