Name:______________________

CH174 Homework #9 Spring 2021-Due Wednesday 4/28 by 7 pm on lecture gradescope page.

1. Determine if the following are oxidation or reduction reactions, circle O for oxidation and R for
reduction.
OH O
O R
O R

O
NH NH2 OH OH O R
O R

2. Draw a mechanism for the following reaction

O O 1) NaOCH3 O

O 2) Br
3) H3O+ heat
Name:______________________
3. Draw the structure of the major organic product of these reactions.
1:1 mix of enantiomers

a) O
H3O+ mix of diastereomers
O O
heat
O 1 product

1:1 mix of enantiomers

b) O O 1. NaOCH2CH3

O 2. Cl mix of diastereomers

3. H3O+ heat
1 product

1:1 mix of enantiomers

O
heat
c) mix of diastereomers
OH

O 1 product

1:1 mix of enantiomers

O
NH4CN H3 O+
mix of diastereomers
d) H

1 product

1:1 mix of enantiomers

e) Jones
OH
H2CrO4 mix of diastereomers

1 product

1:1 mix of enantiomers

1. NaBH4
f)
mix of diastereomers
O 2. H2O
1 product

4. Provide reagents necessary to transform the given starting materials (on the left) to the indicated
products. If the transformation requires more than 1 step, clearly specify which reagents belong
to which step, and the order in which the steps are performed.

O
O H 3N
H OH
H

HO HO

O O O