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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 NeCheck the box under each D-hexose. If there are none, check the None of the above box under the table. НО НО- н CH2OH C=0 H H ОН CH2OH НО Н- HO H Н- None of the above. ОН H ОН ОН CH₂OH НО НО- НО CH2OH C-0 H H H CH₂OH Н НО НО H 0 H H ОН CH2OH НО- Н Н CH2OH c=0 Н ОН - ОН CH₂OHin the following molecule the glycosidic bond is circled. CH2OH CH2OH H CH2OH OH HO H H НО H. ОН ÓH True False
- 18-82 Identify each of the following Haworth projection formulas as an a-D-monosaccharide or a B-D-monosaccharide. ÇH,OH b. ÇH;OH a. OH Но OH ÓH ÓH ÓH с. CH,OH d. HOCH2 CH;OH OH HỎ OH OH ÓH ÓH 18-83 Draw thCheck the box under each ketose. If there are none, check the None of the above box under the table. H H- НО НО c=0 ОН H Н CH2OH Н. Н- HO- Н- None of the above. c=0 ОН -Н ОН CH2OH H- НО- CH₂OH 1 c=0 ОН -Н CH2OH НО НО- c=0 H H— ОН CH₂OH ЗЕР Н c=0 Н- -ОН I I H Н- - ОН ОН CH₂OH H— x7. Draw the Haworth structure for the following monosaccharides a. H НО H c=0 H + но - н 3 4 Н 5 - ОН - OH 애 CH₂OH 6 D-Mannose b. H 0 = с H - C - OH HO-C - H H - C - OH H - C - ОН CH₂OH Glucose
- Click on the glycosidic linkage НО CH2OH ОН ОН CH₂OH ОН ОН ОНОН 2. the Fischer projection that corresponds to the monosaccharide shown in the box. О н HO OH но- OH НО 0 OH OH OH H-OH -ОН 3. the Haworth projection that corresponds to the structure shown in the box. OCH, НО OH athul algasida О Н H-OH H-OH но-н но- HO -O OCH, OH O H H-OH НО-Н H-OH H-OH OH ОН НО НО OOCH, HO H-OH но-н но-н OH H-OH OH НО OH OCH, OH OH О н H-OH H-OH H НО но-н ОН НО -oOCH, ОН он онWhat is the Fischer projection of the monosaccharide from which the following glycoside was prepared? НО. H- H Н CH.OH :0 -OH OH -OH CH₂OH HO- НО H ОН CH₂OH " H -H OH CH₂OH OH НО OH Н- Н- CH₂OH O H OH ОН CH₂OH Ш H— НО НО CH₂OH O OH H -H CH₂OH IV
- 10. Circle the reducing end of each of the disaccharides below. CH2OH CH2OH он о OH OH О ОН -О, ОН ОН OH O- -І OH -Т CH₂OH Н Н ОН I О Т- " CH2OH Н H -IO- OH ОН Н Н T OHClassify the structures as being either an enantiomer, diastereomer or diastereomer/epimer of D-glucose. Structure A: CH H- -OH Structure B: но- H- H- OH Structure C: H- он H- -H D-Glucose: OH || CH CH CH он H- он но -H H- он но он но но- H- но H- OH OH но -- H- -H H -Ç-H Structure A: OH Structure B: OH Structure C: OHm) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer projections for the four aldohexoses that make up this tetrasaccharide are shown below. B C D HOH CHO CHO CHO CHO HO+H HTOH Fонно н HOH HOH H-OH H-OH H-+-OH H-TOHHOH HOH H+OH HOHнтон нон CHOH CHOH CHOH CHOH De D-glue Dalose Datrone i NH Į HOH STEP 1 OH, HO- answer 1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine з no arrows needed here OH н Н ЮН -OH STEP 3 :ÖH н H STEP 2 на это про за поч