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Dienes and Diels-Alder Problems of Organic Chemistry II | CHEM 212, Assignments of Organic Chemistry

Material Type: Assignment; Class: Organic Chemistry II; Subject: Chemistry; University: Bucknell University; Term: Unknown 1989;

Typology: Assignments

Pre 2010

Uploaded on 08/18/2009

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Cl
Cl
Br
CO2Me
CO2Me
Me
CO2Me
Me
Me
MeO2C
CO2Me
Me
HMeO2C
Me
CO2Me
Me
H
Me CO2Me
CO2Me
CO2Me
H
H
O
Provide the products for the following reactions. Be sure to:
1) indicate all relevant stereochemistry.
2) indicate major and minor when mixtures are formed.
3) indicate which product is the kinetic product and which is the thermodynamic product if there is a difference between
the two.
H
H
Br2
(1 eq.)
HI
(1 eq.)
CO2Me CO2Me
AgNO3
EtOH
Br2
(1 eq.)
CO2Me
CO2Me
AgNO3
EtOH
H2O
OMe
O
HBr
(1 eq.)
(1 eq.)
HBr
(2 eq.)
+
O
+
+
CO2Me
CO2Me
+
O
O
OMe
O
+
+
MeO
+
OMe
+
+
1. LDA (2 eq.)
2.
heat
EtO
+
+
OMe
O
O
OMe
Chem 212
Dienes and Diels-Alder Problems
Br
HBr
Br

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Cl Cl Br CO2Me CO2Me Me CO2Me Me Me MeO2C CO (^) 2Me Me

H

MeO2C Me CO2Me Me

H

Me CO2Me CO2Me H CO2Me

H

O

Provide the products for the following reactions. Be sure to:

  1. indicate all relevant stereochemistry.
  2. indicate major and minor when mixtures are formed.
  3. indicate which product is the kinetic product and which is the thermodynamic product if there is a difference between the two.

H

H

Br 2 (1 eq.)

HI

(1 eq.) CO2Me CO2Me AgNO (^3) EtOH Br (1 eq.) CO2Me CO2Me AgNO EtOH

H 2O

OMe

O

HBr (1 eq.) (1 eq.) HBr (2 eq.)

O

CO2Me CO2Me

O

O ∆ ∆

OMe

O

+^ ∆^ +

MeO

+ ∆^ ∆

OMe

  1. LDA (2 eq.)

heat

EtO

OMe

O

∆ ∆ O

OMe

Chem 212 Dienes and Diels-Alder Problems Br HBr Br