Table 25.1 Configurational Relationships Among the Isometric D-Aldotetroses, D-Aldopentoses, and D-Aldohexoses CHO H- • HO- CH,OH D-Glyceraldehyde СНО CHO OH Но- H. H H- HO- CHOH CH,OH D-Erythrose D-Threose CHO CHO CHO CHO H- HO- HO H FOH Но H- H OH HO HO H- HO- HO- HO- CH,OH ČHOH ČHOH ČHOH D-Ribose D-Arabinose D-Xylose D-Lyxose СНО СНО CHO CHO СНО СНО СНО CHO ОН НО -H- H- -ОН НО H- H- OH HO- H. -ОН НО- H. FOH H- OH HO H- HO- FOH H FOH HO- H- Но- H- -HO- H- HO- H -HO- H- OH HO- HO- HO H- но- H- HO- HO- H- HO- HO- H- HO- H FOH OH HO- CH,OH ČH,OH ČH,OH CH,OH ČH,OH CH,OH ČH,OH ČH,OH D-Allose D-Altrose D-Glucose D-Mannose D-Gulose D-Idose D-Galactose D-Talose

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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An important technique for establishing relative configurations among isomeric
aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific
example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.

Table 25.1 Configurational Relationships Among the Isometric D-Aldotetroses, D-Aldopentoses,
and D-Aldohexoses
CHO
H-
• HO-
CH,OH
D-Glyceraldehyde
СНО
CHO
OH
Но-
H.
H
H-
HO-
CHOH
CH,OH
D-Erythrose
D-Threose
CHO
CHO
CHO
CHO
H-
HO-
HO
H FOH
Но
H-
H
OH
HO
HO
H-
HO-
HO-
HO-
CH,OH
ČHOH
ČHOH
ČHOH
D-Ribose
D-Arabinose
D-Xylose
D-Lyxose
СНО
СНО
CHO
CHO
СНО
СНО
СНО
CHO
ОН НО
-H-
H-
-ОН НО
H-
H-
OH HO-
H.
-ОН НО-
H.
FOH
H-
OH HO
H-
HO-
FOH
H FOH HO-
H-
Но-
H-
-HO-
H-
HO-
H
-HO-
H-
OH HO-
HO-
HO
H-
но-
H-
HO-
HO-
H-
HO-
HO-
H-
HO-
H FOH
OH
HO-
CH,OH
ČH,OH
ČH,OH
CH,OH
ČH,OH
CH,OH
ČH,OH
ČH,OH
D-Allose
D-Altrose
D-Glucose
D-Mannose
D-Gulose
D-Idose
D-Galactose
D-Talose
Transcribed Image Text:Table 25.1 Configurational Relationships Among the Isometric D-Aldotetroses, D-Aldopentoses, and D-Aldohexoses CHO H- • HO- CH,OH D-Glyceraldehyde СНО CHO OH Но- H. H H- HO- CHOH CH,OH D-Erythrose D-Threose CHO CHO CHO CHO H- HO- HO H FOH Но H- H OH HO HO H- HO- HO- HO- CH,OH ČHOH ČHOH ČHOH D-Ribose D-Arabinose D-Xylose D-Lyxose СНО СНО CHO CHO СНО СНО СНО CHO ОН НО -H- H- -ОН НО H- H- OH HO- H. -ОН НО- H. FOH H- OH HO H- HO- FOH H FOH HO- H- Но- H- -HO- H- HO- H -HO- H- OH HO- HO- HO H- но- H- HO- HO- H- HO- HO- H- HO- H FOH OH HO- CH,OH ČH,OH ČH,OH CH,OH ČH,OH CH,OH ČH,OH ČH,OH D-Allose D-Altrose D-Glucose D-Mannose D-Gulose D-Idose D-Galactose D-Talose
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