Chem 14D Final Exam Review Packet P.

The final exam is cumulative, but with an emphasis on the more recent material (since exam 2). In this review packet, any questions that deal with Chapters 19/20 are shown in red font since there was not a separate problem set on these topics. 1. Draw the major product for each of the following reactions. Where applicable, answers without relative stereochemistry will be given zero credit. a.
Me Et H2, Pd/C EtOH

b.
1. O3, CH2Cl2 2. DMS

c.
CO2Me + CO2Me heat

d.
HgSO4 H2SO4, H2O

e.
O H+ MeOH (excess)

f.
O OMe H+ EtOH

g.
O OMe MeMgBr (2 equiv)

h.
Br2 FeBr3

Garg, Spring 2011

Chem 14D Final Exam Review Packet P.2

2. Provide the missing reagents for the transformations shown below. a.

OH OMe

b.

Br

c.
O OH

d.
OH

e.
O N Me

f.
O

g.
O O Me

h.
O OH OH

i.
O OH O Cl

j.
NH2 NO2

Garg, Spring 2011

Chem 14D Final Exam Review Packet P.3

3. Provide the missing reagents, products, and/or intermediates in the schemes below. a.
?
Br
?

? ?
EtNH2 !

SOCl2
?

O OH

O O

? ?
MeOH H+ O N

b.
O Cl AlCl3

NaBH4 EtOH

PBr3 CH2Cl2

O Zn(Hg) HCl Cl

1. Mg, Et2O 2. CO2 3. H+ work-up

CO2H

Garg, Spring 2011

Chem 14D Final Exam Review Packet P.4

4. Provide detailed arrow-pushing mechanisms for the following transformations. a.

Cl O MeO O AlCl3 MeO O O

b.
HNO3 H2SO4 NO2

c.
O OH EtOH H+, Heat O OEt

d.
O O H O NaOH, H2O Heat H

e.
O 1. LDA 2. Br O

f.
OH NaOH H2O O

Garg, Spring 2011

Chem 14D Final Exam Review Packet P.5

5. Provide syntheses of the following target molecules. You may use common reagents, solvents, fragments of 2-carbons or less (these fragments may contain atoms other than just carbon, including hydrogen, oxygen, MgBr, and Li), and any of the compounds shown in the Chem 14D Toolbox. It is not necessary to show mechanisms or a retrosynthetic analysis in your solution.
Chem 14D Toolbox
O Cl O H O H O Cl

a.
O OMe

OH

b.
O H

Br

c.
Me N

d.
MeO O O

e.
O OH

(ibuprofen)

Garg, Spring 2011