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

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

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D-3-keto-glucose⟶L-3-keto-glucose

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

Above is a Fischer projection of the monosaccharide D-3-keto-glucose. Which one of the following Fischer projections is of the monosaccharide L-3-keto-glucose?

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

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

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α-D-altro-2-heptulose

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

Above is a Haworth projection of the monosaccharide α-D-altro-2-heptulose. Which one of the following Haworth projections is of the monosaccharide α-L-altro-2-heptulose?

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

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Matching Polysaccharides with Their Descriptions

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Match each of the following polysaccharides with their corresponding descriptions.
Note: Each choice will be used exactly once.

	Your Choice	Prompt
	Drop Your Choice Here	1. glycogen
	Drop Your Choice Here	2. amylopectin
	Drop Your Choice Here	3. chitin
	Drop Your Choice Here	4. amylose
	Drop Your Choice Here	5. cellulose

Drag one of the choices below:

• A. structural material in arthropods and fungi
• B. glucose storage found in skeleton muscle and liver cells
• C. highly branched glucose polymer found in plants that is readily digested by humans and other mammals
• D. unbranched energy storage in plants
• E. structural material in plant cell walls

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Polysaccharides from Functional Descriptions

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Which one of the following polysaccharides correspond to the description 'structural material in plant cell walls'.

• A. amylopectin
• B. amylose
• C. cellulose
• D. chitin
• E. glycogen

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Monosaccharide Types from Fischer Projections (Multiple Answers)

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Fischer classification problem

H		.		O
.	\		//		.
.	.	C		.	.
HO	.	.	.	.	H
	.	.	.	.
H	.	.	.	.	OH
	.	.	.	.
H	.	.	.	.	OH
	.	.	.	.
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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Furanose Monosaccharide Classification from Haworth Projections (Multiple Answers)

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Haworth classification problem

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

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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Pyranose Monosaccharide Classification from Haworth Projections (Multiple Answers)

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Haworth classification problem

H	.	.	.	H	.	.	.	.	.	CH2OH
	.	.	.	.		.	.	.	.
	.	.	/	.	.	.	O	.	.
.	.	/	.	CH2OH	.	.	.	\	.	.
	/	.	.	Haworth			.	.	\
.	\	.	.				.	.	/	.
	.	\	.	OH	.	HO	.	/	.
HO	.	.	\	.	.	.	/	.	.	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 Haworth Projections from Fischer Projections (Multiple Choice)

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D-sorbose⟶α-D-sorbose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

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Pyranose Haworth Projections from Fischer Projections (Multiple Choice)

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L-ido-2-heptulose⟶α-L-ido-2-heptulose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

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Furanose Fischer Projections from Haworth Projections (Multiple Choice)

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β-D-tagatose⟶D-tagatose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

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Pyranose Fischer Projections from Haworth Projections (Multiple Choice)

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α-D-gulo-2-heptulose⟶D-gulo-2-heptulose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

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