Chemistry 20 Section Handout: Module 3 Spring 2016

Solutions for the the "B" problems

1. Provide comple curved-arrow mechanisms for the following transformations.

O OH

H H3C HO O O
(b) H3O+
OH
H3C H3C CH3
O
HO OH HO

H OH2

H2O:
H OH
HO O O
O

H H3C
H3C CH3
OH HO
H3C
O
HO H OH

"lone pair push"

OH
H
HO HO O

O
H3C CH3
H H3C
HO
OH
H3C
OH OH OH we use this symbol to
mean "is equivalent to"

OH
H+ transfer H3C
H
OH
H3C
O OH OH
Solutions for the the "B" problems
2. Fill in each box with the product of the indicated transformation.

1. CrO3 py OH
OH
2. Li (2 eq), Et2O
(b)
Cl
3. H+ workup

CrO3 py
H+ workup

O O O
Li (2 eq),

Cl Et2O Li

Individual reactions are shown here for teaching purposes. On an exam, you do not need to write the
product of each step when answering this type of "predict the product" box question.

3. Provide multistep synthesis for each of the desired products using the indicated starting materials.

(b) Starting Materials:

O

OH

plus any compounds containing Desired Product

two or fewer carbons

1. Et2CuLi
CrO3 py
2. H+ workup

O 1. MgBr HO CrO3 O

H 2. H+ workup H