#6 B D F INSTRUCTIONS: Characterize the members of each of the following pairs of structures as  enantiomers, diastereomers or neither enantiomers nor diastereomers.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter20: Carbohydrates
Section: Chapter Questions
Problem 20.49P
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#6 B D F

INSTRUCTIONS: Characterize the members of each of the following pairs of structures as  enantiomers, diastereomers or neither enantiomers nor diastereomers.

6. Characterize the members of each of the following pairs of structures as (i) enantiomers,
(ii) diastereomers or (iii) neither enantiomers nor diastereomers.
a.
C.
e.
H-
HO-
CHO
-OH
-H
H-OH
CH₂OH
CH₂OH
T
C=0
HO-H
НО
HO-H
CH₂OH
CHO
H-OH
Н H-OH
HO-H
CH₂OH
and
CHO
H-OH
-ОН
H-OH
H-OH
-ОН
CH₂OH
and
and HO-
CH₂OH
I
C=0
HO-H
H-OH
-ОН
CH₂OH
CHO
HO H
HO-H
H-OH
CH₂OH
c.
Melting point
d. Solubility in a chiral solvent
e.
f.
g.
b.
d.
c. D-erythrulose & D-psicose
d. D-talose & D-gulose
f.
e. dihydroxyacetone & D-tagatose
f. D-idose & D-threose
CHO
H-OH
HO-H
CH₂OH
CHO
H-OH
HO-H
Freezing point
Reaction with ethanol (achiral compound)
Reaction with (+)-lactic acid (chiral compound)
H-OH
HO-H
CH₂OH
CH₂OH
I
C=O
H OH
H-OH
CH₂OH
CHO
H-H
and HO-H
and
and
CH₂OH
CHO
HO-H
НО-
H-OH
HO-H
7. D-glucose and L-glucose would be expected to show differences in which of the following
properties? (Answer the items as different or not different)
a. Solubility in an achiral solvent
b. Density
H-OH
CH₂OH
CH₂OH
C=0
H-H
H-OH
-ОН
CH₂OH
8. Indicate whether the following pairs of monosaccharides are aldoses or ketoses.
a. D-altrose & D-xylose
b. D-arabinose & D-glyceraldehyde
Transcribed Image Text:6. Characterize the members of each of the following pairs of structures as (i) enantiomers, (ii) diastereomers or (iii) neither enantiomers nor diastereomers. a. C. e. H- HO- CHO -OH -H H-OH CH₂OH CH₂OH T C=0 HO-H НО HO-H CH₂OH CHO H-OH Н H-OH HO-H CH₂OH and CHO H-OH -ОН H-OH H-OH -ОН CH₂OH and and HO- CH₂OH I C=0 HO-H H-OH -ОН CH₂OH CHO HO H HO-H H-OH CH₂OH c. Melting point d. Solubility in a chiral solvent e. f. g. b. d. c. D-erythrulose & D-psicose d. D-talose & D-gulose f. e. dihydroxyacetone & D-tagatose f. D-idose & D-threose CHO H-OH HO-H CH₂OH CHO H-OH HO-H Freezing point Reaction with ethanol (achiral compound) Reaction with (+)-lactic acid (chiral compound) H-OH HO-H CH₂OH CH₂OH I C=O H OH H-OH CH₂OH CHO H-H and HO-H and and CH₂OH CHO HO-H НО- H-OH HO-H 7. D-glucose and L-glucose would be expected to show differences in which of the following properties? (Answer the items as different or not different) a. Solubility in an achiral solvent b. Density H-OH CH₂OH CH₂OH C=0 H-H H-OH -ОН CH₂OH 8. Indicate whether the following pairs of monosaccharides are aldoses or ketoses. a. D-altrose & D-xylose b. D-arabinose & D-glyceraldehyde
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