Chapter 28: Question 6. (page 1106)

Short Answer
Answer
a.
- Compound A: L-sugar
- Compound B: L-sugar
- Compound C: D-sugar
b.
- A and B are diastereomers.
- A and C are enantiomers.
- B and C are diastereomers
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Chapter 28: Question 6. (page 1106)

Answer
a.
b.
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Identify 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.
The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed.

Question: Draw each stereogenic center using a Fischer projection formula.
Question: Label each stereogenic center as RorS.
Question: Assign R,S designations to each stereogenic center in glucose.
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