Chapter 25: Problem 21

Convert each Haworth projection to an open-chain form and then to a Fischer projection. Name the monosuccharide you have drawn. (a) OCC1OC(O)C(O)C(O)C1O (b) OCC1OC(O)C(O)C1O \(25.21\) Convert each chair conformation to an open-chain form and then to a Fischer projection. Name the monosaccharide you have drawn. (a) OCC(O)C(O)C(O)C(O)CO (b) OCC1OC(O)C(O)C(O)C1O

Short Answer

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Question: Convert the given Haworth projections to their open-chain forms, then to their Fischer projections, and finally, identify the monosaccharide for each case. (a) Haworth projection: OCC1OC(O)C(O)C(O)C1O (b) Haworth projection: OCC1OC(O)C(O)C1O Answer: (a) The monosaccharide is D-glucose. Fischer projection: O | C- O - C | H- C - OH | H- C - OH | H- C - OH | CH2OH (b) The monosaccharide is D-ribose. Fischer projection: O | C- O - C | H- C - OH | H- C - OH | CH2OH

Step by step solution

Convert Haworth projection to an open-chain form

To convert the Haworth projection to an open-chain form, break the cyclic structure by opening the ring between C1 and C5. Now, we have: OCC(O)C(O)C(O)C(O)CO.

Convert the open-chain form to a Fischer projection

To create the Fischer projection, orient the molecule vertically, with the most oxidized carbon on top. Draw horizontal lines for the groups on the right of the open-chain form and vertical lines for those on the left: O | C- O - C | H- C - OH | H- C - OH | H- C - OH | CH2OH

Identify and name the monosaccharide

According to the Fischer projection, the monosaccharide is D-glucose, a common sugar found in many carbohydrates. (b) OCC1OC(O)C(O)C1O

Convert Haworth projection to an open-chain form

To convert the Haworth projection to an open-chain form, break the cyclic structure by opening the ring between C1 and C4. Now, we have: OCC(O)C(O)C(O)CO.

Convert the open-chain form to a Fischer projection

To create the Fischer projection, orient the molecule vertically and place the most oxidized carbon at the top. Draw horizontal lines for the groups on the right of the open-chain form and vertical lines for those on the left: O | C- O - C | H- C - OH | H- C - OH | CH2OH

Identify and name the monosaccharide

According to the Fischer projection, the monosaccharide is D-ribose, an important component in nucleotide and RNA synthesis.

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Step by step solution

Convert Haworth projection to an open-chain form

Convert the open-chain form to a Fischer projection

Identify and name the monosaccharide

Convert Haworth projection to an open-chain form

Convert the open-chain form to a Fischer projection

Identify and name the monosaccharide

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