QO-IV Problems 4

1. Indicate the main Diels-Alder reaction product

a. butadiene + maleic anhydride
b. 2-methylbutadiene +diethyl fumarate
c. 2-methoxybutadiene + acrolein
d. cyclopentadiene + benzoquinone
e. (E)-1,3-pentadiene + maleic acid
f. 1-methoxycyclopentadiene + 2-nitropropene
g. (Z)-1,3-hexadiene +benzyne
h. (E,E)-2,4-hexadiene + methyl acrylate
i. 1,4-dimethylcyclopentadiene + ethyl vinyl ketone
j. furan + ethyl 3-nitroacrylate
k. 2,3-dimethylcyclopentadiene + butynedioic acid
l. hexachlorocyclopentadiene + norbornadiene
m. 3-sulfolene + dimethyl fumarate
n. 1,3-cyclohexadiene + trans-bis(benzenesulfonyl) ethylene
o. 5-ethylcyclopentadiene + nitroethylene
p. trans-1-methoxy -3-trimethylsilyloxy-1,3-butadiene +2-methyl acrolein

2. Draw the reaction product

O O

+ +

O
O AcO OMe
OAc +
+ O
O
N
O NC CN Ph
N N +
NC CN N
O

3. Propose a synthesis for

SO2Ph
CO2H

CH3

PPh 3
BBN

4. Find the Diels-Alder disconnections and draw the starting materials

CO2Me
H O

O
CO2Me
H O
CO2Me Ph O
MeO 2C

OHC Ph