1) Devise a reaction sequence that will synthesize the following targets from
benzene. You may use any additional organic or inorganic reagents.
H
COOH
NO 2
O
Cl
Br
OCH3
Cl
CO 2CH 2CH3
2) Determine the missing reagents in the following reaction sequence:
?
O
?
O
BH
B
O
O
3) Propose a mechanism for the following reaction sequence using curved arrow
formalism.
Br
OBu
Pd(OAc) 2
+
PPh 3
NEt 3
H 3O+
O
4)
a) Propose a synthesis of the following product using a Heck reaction.
b) Next propose the synthesis of all necessary organic starting materials from
ethyne and benzene as your only sources of carbon.
H 3COCHN
5) Show how acetylene can form the basis for a Suzuki reagent in order to make
conjugated dienes by developing a synthesis of the following target: