N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Ne

Chemistry
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Chapter1: Chemical Foundations
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N-NHPH
CHO
CH2OH
H-
C=N-NHPH
Но-
-H-
3 equiv
Но-
-H-
3 equiv
Но-
PHNHNH2
PHNHNH,
H-
H-
OH
H-
-O-
H-
H-
-HO-
H-
-HO-
ČH2OH
ČH2OH
ČH2OH
D-glucose
osazone
D-fructose
+ NH3 + PHNH2
+ 2 H20
The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of
phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps:
1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1;
2. Elimination of ammonia to yield phenylhydrazone 2;
3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3;
4. Proton transfer yields carbinolamine 4;
5. Elimination of water yields the final product osazone.
Write out the mechanism on a separate sh
of paper and then draw the structure of tetrahedral intermediate 3.
NH
НО-
-H
H-
-ОН
H-
-ОН
ОН
Glucose keto imine
Previous
Ne
Transcribed Image Text:N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Ne
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