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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A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani-Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A-C?
Question: Draw each stereogenic center using a Fischer projection formula.
Question:Draw the structure of (a) a ketotetrose; (b) an aldopentose; (c) an aldotetrose
Question: Convert the ball-and-stick model to a Fischer projection.

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.

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