Chemistry 243

Problem Set #5
1) How would you synthesize the following from cyclohexanol? a)
Br

b)

c)

2)

What are the products of the following reactions? Name the products a)
O O

1) LiAlH4 2) workup

ethyl hexanoate

b)

1) LDA (strong non-nucleophilic base) +

HC C

? 2) workup

2-Pentanone

1-butyne

3)

Name the below molecule. How would you synthesize it from Pentanal (a 5carbon aldehyde molecule) and 1-propanol?
OH

4)

Draw the products of the following reactions. Assign stereochemical designations (R or S). Draw all possible stereoisomers for each reaction. a)
KMnO4 / OH

?
b)
1) RCOOOH

?
2) OH