Chapter 28: Problem 28.41 (page 1147)
For D-arabinose:
- Draw its enantiomer.
- Draw an epimer at C3.
- Draw a diastereomer that is not an epimer.
- Draw a constitutional isomer that still contains a carbonyl group.
Short Answer
Answer
a.
b.
c.
d.
Chapter 28: Problem 28.41 (page 1147)
For D-arabinose:
Answer
a.
b.
c.
d.
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Get started for freeIdentify the compounds A-D. A D-aldopentose A is oxidized with to an optically inactive aldaric acid. B. A undergoes the Kiliani-Fischer synthesis to yield C and D. C is oxidized to an optically active aldaric acid. D is oxidized to an optically inactive aldaric acid.
Question: Convert the ball-and-stick model to a Fischer projection.
Question: Label each Haworth projection as an ฮฑ or ฮฒ anomer and convert the Haworth projection to a six-membered ring with wedges and dashed wedges.
a.
b.
Question: Draw each stereogenic center using a Fischer projection formula.
The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, , in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the or anomers of D-idose. Explain why the more stable conformation has the group in the axial position.
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