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2886453 Organic Chemistry 342 Reactions

2886453 Organic Chemistry 342 Reactions

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Published by: 09021982 on Apr 28, 2013
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© Gregory R Cook page Chem Exam ReactionNorth Dakota State University 
REACTIONSFor Final Exam
Reactions for Final Exam
 Although you don’t need to know all of the mechanisms for these reactions, knowing themmakes it easier to understand the reactions and to figure out a reaction if you forget it. Consult thelecture notes for more details on the mechanisms and issues of stereo- and regioselectivity.
ELECTROPHILIC ADDITION REACTIONS
HXX+X
OCH
3
HgO
2
CCF
3
NaBH
4
OCH
3
Hg(O
2
CCF
3
)
2
CH
3
OH
RROHROHgSO
4
H
3
O
+
enol ketone
CH
3
CH
3
OMCPBA
CH
3
CH
3
OHBrBr
2
H
2
O
CH
3
BH
3
H
2
O
2
, OH
-
CH
3
HOH
CH
3
Hg(OAc)
2
CH
3
OHH
2
ONaBH
4
1)2)
CH
3
OsO
4
CH
3
OHNaHSO
3
OH1)2)
 
© Gregory R Cook page Chem Exam ReactionNorth Dakota State University 
ELECTROPHILIC SUBSTITUTION REACTIONS
Br
2
FeBr
3
Br
Cl
2
FeCl
3
Cl
I
2
CuI
2
I
HNO
3
H
2
SO
4
NO
2
SO
3
H
2
SO
4
SO
3
H
R-ClAlCl
3
R
R ClOAlCl
3
RO
OBr
2
CH
3
CO
2
HOBr
Br
2
PBr
3
OOHOOH1)2) H
2
OBr
 
© Gregory R Cook page Chem Exam ReactionNorth Dakota State University 
NUCLEOPHILIC ADDITION REACTIONS
Ph HOPh HHOCNHCNcyanohydrinKOH
OHO OHH
2
Ohydrate+H
+
or
-
OHcatalyst
OR-NH
2
H
+
NRH
2
O+ +imine
OR
2
NHH
+
NRRH
2
O+ +enamine
OROHH
+
ROOR+2an acetal
1,4-addition
OCH
3
NH
2
ONHCH
3
1,4-addition
O OPh1) Ph
2
CuLi2) H
3
O
+
1,2-addition
O1) PhMgBr2) H
3
O
+
HOPh
1,2-addition
O1) PhLi2) H
3
O
+
HOPh
RClORPh1) PhMgBr2) H
3
O
+
HOPh

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