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문제 1
Classify the following monosaccharides:
문제 2
Draw Fischer projections of L-glucose and L-fructose.
문제 3
Indicate whether each of the following structures is D-glyceraldehyde or L-glyceraldehyde, assuming that the horizontal bonds point toward you and the vertical bonds point away from you (Section 4.7):
a.
b.
c.
문제 4
a. Are d-erythrose and l-erythrose enantiomers or diastereomers?
b. Are l-erythrose and l-threose enantiomers or diastereomers?
문제 5c
c. What sugar is the C-4 epimer of L-gulose?
문제 5d
d. What sugar is the C-4 epimer of D-lyxose?
문제 6a
What are the systematic names of the following compounds? Indicate the configuration (R or S) of each asymmetric center.
a. D-glucose
문제 6b
What are the systematic names of the following compounds? Indicate the configuration (R or S) of each asymmetric center.
b. D-mannose
문제 7
What sugar is the C-3 epimer of D-fructose?
문제 8a
How many stereoisomers are possible for a. a ketoheptose?
문제 8b
How many stereoisomers are possible for b. an aldoheptose?
문제 11
When D-tagatose is added to a basic aqueous solution, an equilibrium mixture of monosaccharides is obtained, two of which are aldohexoses and two of which are ketohexoses. Identify the aldohexoses and ketohexoses.
문제 13b
What monosaccharide is reduced to two alditols, one of which is the alditol obtained from the reduction of
1. D-talose?
2. D-allose?
문제 14a,b
a. Name an aldohexose other than D-glucose that is oxidized to D-glucaric acid by nitric acid.
b. What is another name for D-glucaric acid?
문제 14c
Name another pair of aldohexoses that are oxidized to identical aldaric acids.
문제 15a
What monosaccharides are formed in a modified Kiliani–Fischer synthesis starting with each of the following monosaccharides?
a. D-xylose
문제 16a
What two monosaccharides can be degraded to
a. D-ribose?
문제 16b
What two monosaccharides can be degraded to
b. D-arabinose?
문제 19b
4-Hydroxy- and 5-hydroxyaldehydes exist primarily as cyclic hemiacetals. Draw the structure of the cyclic hemiacetal formed by each of the following:
b. 4-hydroxypentanal
문제 19c
4-Hydroxy- and 5-hydroxyaldehydes exist primarily as cyclic hemiacetals. Draw the structure of the cyclic hemiacetal formed by each of the following:
c. 5-hydroxypentanal
문제 19d
4-Hydroxy- and 5-hydroxyaldehydes exist primarily as cyclic hemiacetals. Draw the structure of the cyclic hemiacetal formed by each of the following:
d. 4-hydroxyheptanal
문제 21
D-Glucose most often exists as a pyranose, but it can also exist as a furanose. Draw the Haworth projection of α-D-glucofuranose
문제 22-23
When glucose undergoes base-catalyzed isomerization in the absence of the enzyme, mannose is one
of the products that is formed (Section 20.5). Why is mannose not formed in the enzyme-catalyzed reaction?
문제 22
Draw the anomers of D-erythrofuranose.
문제 24
Which OH groups are in the axial position in each of the following?
a. β-D-idopyranose
b. α-D-allopyranose
문제 25
Draw the products formed when β-D-galactose reacts with ethanol and HCl. (Show all structures as chair conformers.)
문제 26
Why is only a trace amount of acid used in the formation of an N-glycoside?
문제 28a
Name the following compounds and indicate whether or not each is a reducing sugar:
a.
문제 28b
Name the following compounds and indicate whether or not each is a reducing sugar:
b.
문제 28c
Name the following compounds and indicate whether or not each is a reducing sugar:
c.
