Structure of     Glucose          CHEM 81      Professor Hoover       Allyson Camitta         Ruby Davila      Tamra Fukum...
2Structure of GlucoseAvailable data: Meso compounds are optically inactive  and unsymmetrical compounds are  optically ac...
3Structure of Glucose (cont.)                 Four chiral center  24 = 16 stereoisomers                  possible       ...
4     Possible Structures1)       2)    3)     4)       5)      6)       7)        8)                            Focused ...
Oxidation with HNO3     Dilute nitric acid oxidizes both the      aldehyde and –OH groups of an aldose5      to an aldari...
6     Clue 1: Oxidation with HNO31)       2)    3)    4)       5)       6)        7)        8)                           ...
7Ruff Degradation   An aldose is shortened by one carbon   Steps:   1.   Oxidation of aldose to an aldonic acid with      ...
8Clue 2: Ruff Degradation   Degradation of glucose gives an aldopentose          Further degradation of the aldopentose ...
9Clue 3: Ruff degradation   Degradation of glucose gives an aldopentose    Possible Structures:1)             2)         ...
10     Possible Structures Left      At this point Fischer knew the arrangement     of all atoms except C2
Clue 4: Interchange of Two End Groups       If the product was different then structure A was        glucose.       If p...
Structure of Glucose12
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Organic Chemistry Emil Fischer Glucose

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Organic Chemistry Emil Fischer Glucose

  1. 1. Structure of Glucose CHEM 81 Professor Hoover Allyson Camitta Ruby Davila Tamra Fukumoto Maria Calderon1
  2. 2. 2Structure of GlucoseAvailable data: Meso compounds are optically inactive and unsymmetrical compounds are optically active Aldose contains an aldehyde moiety 6 carbon atom (hex-)Therefore, glucose is an aldohexose. Emil Fischer
  3. 3. 3Structure of Glucose (cont.)  Four chiral center  24 = 16 stereoisomers possible  During this time a method to assign the stereochemistry to the chiral center did not exist D-glucose  Fischer designated the aldohexoses with the -OH group at C-5 projecting to the right as D sugars.
  4. 4. 4 Possible Structures1) 2) 3) 4) 5) 6) 7) 8)  Focused on the D configuration only
  5. 5. Oxidation with HNO3  Dilute nitric acid oxidizes both the aldehyde and –OH groups of an aldose5 to an aldaric acid
  6. 6. 6 Clue 1: Oxidation with HNO31) 2) 3) 4) 5) 6) 7) 8)  Glucose is oxidized and optically active  Therefore, it cannot be molecule 1 or 7 since both would give optically inactive aldaric acids
  7. 7. 7Ruff Degradation An aldose is shortened by one carbon Steps: 1. Oxidation of aldose to an aldonic acid with bromine and water 2. Oxidative decarboxylation of aldonic acid to an aldose with hydrogen peroxide and ferric sulfate
  8. 8. 8Clue 2: Ruff Degradation Degradation of glucose gives an aldopentose  Further degradation of the aldopentose gives an aldotetrose Possible Structures:1) 2) 3) 4) 5) 6) 7) 8) Followed by oxidation with HNO3 gives an optically inactive aldaric acid  Eliminates 5, 6, 7, 8  Establishes conformation at C4 of glucose
  9. 9. 9Clue 3: Ruff degradation Degradation of glucose gives an aldopentose Possible Structures:1) 2) 3) 4) 5) 6) 7) 8) Followed by oxidation with HNO3 gives an optically inactive aldaric acid  Eliminates 1, 2, 5, 6, 7  Establishes confirmation at C3 of glucose
  10. 10. 10 Possible Structures Left  At this point Fischer knew the arrangement of all atoms except C2
  11. 11. Clue 4: Interchange of Two End Groups  If the product was different then structure A was glucose.  If product after interchange was the same, then structure B was glucose11 A) New product B) Same product
  12. 12. Structure of Glucose12

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