Chemistry 20 Section Handout: Module 3 Spring 2016

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

O Ph

H 1. PhLi (1 eq.)
(a) O
H +
2. H3O
OH
O

O OH

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

2. Fill in each box with the product of the indicated transformation.

HO 1. , H+ cat.
2. Mg, Et2O
(a)
HO Br 3. CO2
4. H+ workup
2. Fill in each box with the product of the indicated transformation.

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

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

OH
(a) Starting Materials:

Any compounds containing

six or fewer carbons
Desired Product

(b) Starting Materials:

O

OH

plus any compounds containing Desired Product

two or fewer carbons