Chapter25: Biomolecules: Carbohydrates
Section25.4: Configurations Of The Aldoses
Problem 9P
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Question
Refer to the structures in the box to answer the questions
![(i) Draw the cyclic beta form of structure II.
(j) Draw the cyclic alpha form of structure II.
(k) Draw the aldonic acid that results when structure VI is treated with Br2 and H₂O.
(1) Draw the aldaric acid that results when structure VI is treated with HNO3.
(m) Is the aldaric acid from the preceding question optically active? Explain.
(n) Draw structural formula for one of the monosaccharides that results when Structure Vis
treated successively with NaBH4 and H₂O.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd6c16c0e-cfd6-4ad1-b723-bdc11d9c41b0%2F38f5c200-ad39-4a48-81ec-67dfd9461ed3%2Feza9fhx_processed.jpeg&w=3840&q=75)
Transcribed Image Text:(i) Draw the cyclic beta form of structure II.
(j) Draw the cyclic alpha form of structure II.
(k) Draw the aldonic acid that results when structure VI is treated with Br2 and H₂O.
(1) Draw the aldaric acid that results when structure VI is treated with HNO3.
(m) Is the aldaric acid from the preceding question optically active? Explain.
(n) Draw structural formula for one of the monosaccharides that results when Structure Vis
treated successively with NaBH4 and H₂O.
![Box 1
OH
H
CH₂OH
OH
О
I
OH
OCH3
CHO
H
-OH
H-OH
НО
H
H
OH
CH₂OH
II
H
CHO
OH
но-
HO-H
HO-H
H-OH НО
CH₂OH
III
(a) What is the relative configuration of Structure I?
(b) What is the relative configuration of Structure III?
(d) Identify one nonreducing sugar from the list.
но-+
(e) Identify one reducing sugar from the list.
(f) Identify a pair of epimers from the list.
CH₂OH
H
H-OH
H-OH
(g) Identify a pair of enantiomers from the list.
(c) Which monosaccharide is an optically inactive meso compound?
-H
CH2OH
IV
CH₂OH
=0
H
OH
НО-
но-т
H
но-
-Н
CH₂OH
V
(h) Draw the enol that is produced when structure V is dissolved in water.
HO
Н
H Н-
НО
CHO
-H
OH
OH
H
CH2OH
VI](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd6c16c0e-cfd6-4ad1-b723-bdc11d9c41b0%2F38f5c200-ad39-4a48-81ec-67dfd9461ed3%2F8g88iso_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Box 1
OH
H
CH₂OH
OH
О
I
OH
OCH3
CHO
H
-OH
H-OH
НО
H
H
OH
CH₂OH
II
H
CHO
OH
но-
HO-H
HO-H
H-OH НО
CH₂OH
III
(a) What is the relative configuration of Structure I?
(b) What is the relative configuration of Structure III?
(d) Identify one nonreducing sugar from the list.
но-+
(e) Identify one reducing sugar from the list.
(f) Identify a pair of epimers from the list.
CH₂OH
H
H-OH
H-OH
(g) Identify a pair of enantiomers from the list.
(c) Which monosaccharide is an optically inactive meso compound?
-H
CH2OH
IV
CH₂OH
=0
H
OH
НО-
но-т
H
но-
-Н
CH₂OH
V
(h) Draw the enol that is produced when structure V is dissolved in water.
HO
Н
H Н-
НО
CHO
-H
OH
OH
H
CH2OH
VI
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