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-glycero-D-gluco-heptose⟶L-glycero-L-gluco-heptose

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

Above is a Fischer projection of the monosaccharide D-glycero-D-gluco-heptose. Which one of the following Fischer projections is of the monosaccharide L-glycero-L-gluco-heptose?

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

Check Answer

 

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

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α-D-galacto-2-heptulose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

Check Answer

 

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. amylose
	Drop Your Choice Here	4. cellulose
	Drop Your Choice Here	5. chitin

Drag one of the choices below:

• A. also know as resistant starch, because it has no branches and it is resistant to digestion
• B. moderately branched energy storage in plants
• C. polymer of β-linked glucose units found in plants
• D. animal molecule composed of linear chains of α-(1,4) D-glucose residues connected through α-(1,6) linkages
• E. major structural component of arthopod (e.g., insects) exoskeletons

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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 arthropods and fungi'.

• 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

.	.	CH2OH
.			==O
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

Check Answer Clear Selection

 

Furanose Monosaccharide Classification from Haworth Projections (Multiple Answers)

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Haworth classification problem

H	.	.	.	O	.	.	.	H
.	.	⟋		.	⟍		.	.
	⟋	.	.			.	⟍
.	\	.	H	.	HO	.	/	.
.	.	\	.	.	.	/	.	.
CH2OH	.	.	.	.	.	.	.	OH
	.	.	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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Pyranose Monosaccharide Classification from Haworth Projections (Multiple Answers)

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Haworth classification problem

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

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D-fructose⟶α-D-fructose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

Check Answer

 

Pyranose Haworth Projections from Fischer Projections (Multiple Choice)

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L-idose⟶α-L-idose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

Check Answer

 

Furanose Fischer Projections from Haworth Projections (Multiple Choice)

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α-L-lyxose⟶L-lyxose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

Check Answer

 

Pyranose Fischer Projections from Haworth Projections (Multiple Choice)

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α-D-altrose⟶D-altrose

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

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

• A.

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

• B.

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

• C.

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

• D.

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

• E.

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

Check Answer