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Chapter 28: Question 28.14 (page 1106)

Question: Convert each Haworth projection to its acyclic form.

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Conversion of Haworth projection into acyclic form

To convert each Haworth projection into its acyclic form:

  • Draw the C skeleton with the CHO on the top and the on the bottom.
  • Draw in the OH group farthest from the C=O. A group drawn up means a D sugar; a group drawn down means an L sugar.
  • Add the other three stereogenic centers, counterclockwise around the ring. “Up” groups go on the left, and “down” groups go on the right.
02

Explanation

a. The acyclic form of the given Haworth projection is shown as:

The OH placed below the side in the Haworth projection is now put in the right direction and vice-versa.

Conversion into acyclic form for a.

b. The acyclic form of the given Haworth projection is shown as:

Conversion into acyclic form for b.

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Most popular questions from this chapter

Question: Referring to Figure 28.5, which d-ketohexoses have the S configuration at C3?

Fig. 28.5

For D-arabinose:

  1. Draw its enantiomer.
  2. Draw an epimer at C3.
  3. Draw a diastereomer that is not an epimer.
  4. Draw a constitutional isomer that still contains a carbonyl group.

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.

Consider the following six compounds (A-F).


How are the two compounds in each pair related? Choose from enantiomers, epimers, diastereomers but not epimers, constitutional isomers, and identical compounds.

A and B

A and C

B and C

A and D

E and F

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.
See all solutions

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