10: Carbohydrates

Students classify monosaccharides using Fischer and Haworth projections, identify anomers and epimers, and analyze glycosidic bond formation in disaccharides.

LibreTexts reference: Unit 3, Chapter 1: Carbohydrates

Fischer Projections for Monosaccharides with D to L Configuration

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D-gulo-2-heptulose⟶L-gulo-2-heptulose

.	.	CH2OH
.			==O
H	.	.	.	.	OH
	.	.	.	.
H	.	.	.	.	OH
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
H	.	.	.	.	OH
	.	.	.	.
.	.	CH2OH

Above is a Fischer projection of the monosaccharide D-gulo-2-heptulose. Which one of the following Fischer projections is of the monosaccharide L-gulo-2-heptulose?

• A.

  .	.	CH2OH
  .			==O
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  .	.	CH2OH

• B.

  .	.	CH2OH
  .			==O
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

• C.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

• D.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  .	.	CH2OH

• E.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

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D/L Monosaccharide Configurations from Haworth Projections (Multiple Choice)

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β-D-psicose

CH2OH	.	.	.	O	.	.	.	OH
.	.	⟋		.	⟍		.	.
	⟋	.	.			.	⟍
.	\	.	OH	.	HO	.	/	.
.	.	\	.	.	.	/	.	.
H	.	.	.	.	.	.	.	CH2OH
	.	.	H	.	H	.	.

Above is a Haworth projection of the monosaccharide β-D-psicose. Which one of the following Haworth projections is of the monosaccharide β-L-psicose?

• A.

  H	.	.	.	O	.	.	.	CH2OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	H	.	H	.	/	.
  .	.	\	.	.	.	/	.	.
  CH2OH	.	.	.	.	.	.	.	OH
  	.	.	OH	.	HO	.	.

• B.

  H	.	.	.	O	.	.	.	CH2OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	OH	.	H	.	/	.
  .	.	\	.	.	.	/	.	.
  CH2OH	.	.	.	.	.	.	.	OH
  	.	.	H	.	HO	.	.

• C.

  H	.	.	.	O	.	.	.	CH2OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	H	.	HO	.	/	.
  .	.	\	.	.	.	/	.	.
  CH2OH	.	.	.	.	.	.	.	OH
  	.	.	OH	.	H	.	.

• D.

  H	.	.	.	O	.	.	.	OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	H	.	H	.	/	.
  .	.	\	.	.	.	/	.	.
  CH2OH	.	.	.	.	.	.	.	CH2OH
  	.	.	OH	.	HO	.	.

• E.

  H	.	.	.	O	.	.	.	CH2OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	OH	.	HO	.	/	.
  .	.	\	.	.	.	/	.	.
  CH2OH	.	.	.	.	.	.	.	OH
  	.	.	H	.	H	.	.

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Monosaccharide Types from Fischer Projections (Multiple Answers)

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Fischer classification problem

H		.		O
.	\		//		.
.	.	C		.	.
HO	.	.	.	.	H
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
.	.	CH2OH

The diagram above shows a Fischer projection of an unnamed monosaccharide.
Your task is to classify the sugar based on the provided categorizations below. Carefully analyze the structure and check the three categorizations that apply.
Instructions:

• You are required to select exactly three (3) boxes.
• Selecting fewer or more than three boxes will be marked as incorrect.
• No partial credit will be awarded.

• A. triose (3)
• B. tetrose (4)
• C. pentose (5)
• D. hexose (6)
• E. D-configuration
• F. L-configuration
• G. aldose
• H. ketose
• I. 3-ketose

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Classifying Furanose Monosaccharides from Haworth Projections

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Haworth classification problem

H	.	.	.	O	.	.	.	OH
.	.	⟋		.	⟍		.	.
	⟋	.	.			.	⟍
.	\	.	H	.	HO	.	/	.
.	.	\	.	.	.	/	.	.
CH2OH	.	.	.	.	.	.	.	H
	.	.	OH	.	H	.	.

The diagram above shows a Haworth projection of an unnamed monosaccharide.
Your task is to classify the sugar based on the provided categorizations below. Carefully analyze the structure and check the five categorizations that apply.
Instructions:

• You are required to select exactly five (5) boxes.
• Selecting fewer or more than five boxes will be marked as incorrect.
• No partial credit will be awarded.

• A. pentose (5)
• B. hexose (6)
• C. septose (7)
• D. D-configuration
• E. L-configuration
• F. aldose
• G. ketose
• H. furanose
• I. pyranose
• J. α-anomer
• K. β-anomer

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Matching Pyranose Monosaccharides to Haworth Projection Categories

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Haworth classification problem

HO	.	.	.	CH2OH	.	.	.	.	.	CH2OH
	.	.	.	.		.	.	.	.
	.	.	/	.	.	.	O	.	.
.	.	/	.	H	.	.	.	\	.	.
	/	.	.	Haworth			.	.	\
.	\	.	.				.	.	/	.
	.	\	.	OH	.	HO	.	/	.
H	.	.	\	.	.	.	/	.	.	OH
	.	.	.	.	.	.	.	.	.
	.	.	.	H	.	H	.	.	.

The diagram above shows a Haworth projection of an unnamed monosaccharide.
Your task is to classify the sugar based on the provided categorizations below. Carefully analyze the structure and check the five categorizations that apply.
Instructions:

• You are required to select exactly five (5) boxes.
• Selecting fewer or more than five boxes will be marked as incorrect.
• No partial credit will be awarded.

• A. pentose (5)
• B. hexose (6)
• C. septose (7)
• D. D-configuration
• E. L-configuration
• F. aldose
• G. ketose
• H. furanose
• I. pyranose
• J. α-anomer
• K. β-anomer

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Furanose Monosaccharides from Fischer to Haworth Projections (MC)

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D-psicose⟶α-D-psicose

.	.	CH2OH
.			==O
HO	.	.	.	.	H
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
H	.	.	.	.	OH
	.	.	.	.
.	.	CH2OH

Above is a Fischer projection of the monosaccharide D-psicose. Which one of the following Haworth projections is of the monosaccharide α-D-psicose?

• A.

  CH2OH	.	.	.	O	.	.	.	OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	OH	.	HO	.	/	.
  .	.	\	.	.	.	/	.	.
  H	.	.	.	.	.	.	.	CH2OH
  	.	.	H	.	H	.	.

• B.

  CH2OH	.	.	.	O	.	.	.	OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	H	.	HO	.	/	.
  .	.	\	.	.	.	/	.	.
  H	.	.	.	.	.	.	.	CH2OH
  	.	.	OH	.	H	.	.

• C.

  CH2OH	.	.	.	O	.	.	.	CH2OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	H	.	HO	.	/	.
  .	.	\	.	.	.	/	.	.
  H	.	.	.	.	.	.	.	OH
  	.	.	OH	.	H	.	.

• D.

  CH2OH	.	.	.	O	.	.	.	CH2OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	OH	.	HO	.	/	.
  .	.	\	.	.	.	/	.	.
  H	.	.	.	.	.	.	.	OH
  	.	.	H	.	H	.	.

• E.

  H	.	.	.	O	.	.	.	OH
  .	.	⟋		.	⟍		.	.
  	⟋	.	.			.	⟍
  .	\	.	H	.	H	.	/	.
  .	.	\	.	.	.	/	.	.
  CH2OH	.	.	.	.	.	.	.	CH2OH
  	.	.	OH	.	HO	.	.

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Pyranose Monosaccharides in Haworth Projections from Fischer Projections (MC)

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L-altrose⟶β-L-altrose

H		.		O
.	\		//		.
.	.	C		.	.
H	.	.	.	.	OH
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
HO	.	.	.	.	H
	.	.	.	.
.	.	CH2OH

Above is a Fischer projection of the monosaccharide L-altrose. Which one of the following Haworth projections is of the monosaccharide β-L-altrose?

• A.

  H	.	.	.	CH2OH	.	.	.	.	.	H
  	.	.	.	.		.	.	.	.
  	.	.	/	.	.	.	O	.	.
  .	.	/	.	H	.	.	.	\	.	.
  	/	.	.	Haworth			.	.	\
  .	\	.	.				.	.	/	.
  	.	\	.	H	.	HO	.	/	.
  HO	.	.	\	.	.	.	/	.	.	OH
  	.	.	.	.	.	.	.	.	.
  	.	.	.	OH	.	H	.	.	.

• B.

  HO	.	.	.	H	.	.	.	.	.	OH
  	.	.	.	.		.	.	.	.
  	.	.	/	.	.	.	O	.	.
  .	.	/	.	CH2OH	.	.	.	\	.	.
  	/	.	.	Haworth			.	.	\
  .	\	.	.				.	.	/	.
  	.	\	.	OH	.	H	.	/	.
  H	.	.	\	.	.	.	/	.	.	H
  	.	.	.	.	.	.	.	.	.
  	.	.	.	H	.	HO	.	.	.

• C.

  HO	.	.	.	H	.	.	.	.	.	H
  	.	.	.	.		.	.	.	.
  	.	.	/	.	.	.	O	.	.
  .	.	/	.	CH2OH	.	.	.	\	.	.
  	/	.	.	Haworth			.	.	\
  .	\	.	.				.	.	/	.
  	.	\	.	OH	.	H	.	/	.
  H	.	.	\	.	.	.	/	.	.	OH
  	.	.	.	.	.	.	.	.	.
  	.	.	.	H	.	HO	.	.	.

• D.

  H	.	.	.	CH2OH	.	.	.	.	.	OH
  	.	.	.	.		.	.	.	.
  	.	.	/	.	.	.	O	.	.
  .	.	/	.	H	.	.	.	\	.	.
  	/	.	.	Haworth			.	.	\
  .	\	.	.				.	.	/	.
  	.	\	.	H	.	H	.	/	.
  HO	.	.	\	.	.	.	/	.	.	H
  	.	.	.	.	.	.	.	.	.
  	.	.	.	OH	.	HO	.	.	.

• E.

  HO	.	.	.	H	.	.	.	.	.	H
  	.	.	.	.		.	.	.	.
  	.	.	/	.	.	.	O	.	.
  .	.	/	.	CH2OH	.	.	.	\	.	.
  	/	.	.	Haworth			.	.	\
  .	\	.	.				.	.	/	.
  	.	\	.	H	.	H	.	/	.
  H	.	.	\	.	.	.	/	.	.	OH
  	.	.	.	.	.	.	.	.	.
  	.	.	.	OH	.	HO	.	.	.

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Furanose Monosaccharides from Haworth to Fischer Projections (MC)

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β-D-sorbose⟶D-sorbose

CH2OH	.	.	.	O	.	.	.	OH
.	.	⟋		.	⟍		.	.
	⟋	.	.			.	⟍
.	\	.	OH	.	H	.	/	.
.	.	\	.	.	.	/	.	.
H	.	.	.	.	.	.	.	CH2OH
	.	.	H	.	HO	.	.

Above is a Haworth projection of the monosaccharide β-D-sorbose. Which one of the following Fischer projections is of the monosaccharide D-sorbose?

• A.

  .	.	CH2OH
  .			==O
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  .	.	CH2OH

• B.

  .	.	CH2OH
  .			==O
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

• C.

  .	.	CH2OH
  .			==O
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  .	.	CH2OH

• D.

  .	.	CH2OH
  .			==O
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

• E.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

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Fischer Projections of Pyranose Monosaccharides from Haworth Structures

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β-L-allo-2-heptulose⟶L-allo-2-heptulose

HO	.	.	.	H	.	.	.	.	.	CH2OH
	.	.	.	.		.	.	.	.
	.	.	/	.	.	.	O	.	.
.	.	/	.	CH2OH	.	.	.	\	.	.
	/	.	.	Haworth			.	.	\
.	\	.	.				.	.	/	.
	.	\	.	OH	.	HO	.	/	.
H	.	.	\	.	.	.	/	.	.	OH
	.	.	.	.	.	.	.	.	.
	.	.	.	H	.	H	.	.	.

Above is a Haworth projection of the monosaccharide β-L-allo-2-heptulose. Which one of the following Fischer projections is of the monosaccharide L-allo-2-heptulose?

• A.

  .	.	CH2OH
  .			==O
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  .	.	CH2OH

• B.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

• C.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

• D.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  .	.	CH2OH

• E.

  .	.	CH2OH
  .			==O
  HO	.	.	.	.	H
  	.	.	.	.
  H	.	.	.	.	OH
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  HO	.	.	.	.	H
  	.	.	.	.
  .	.	CH2OH

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