1. Chemistry 121(001) Winter 2015
Introduction to Organic Chemistry and Biochemistry
Instructor Dr. Upali Siriwardane (Ph.D. Ohio State)
Office: 311 Carson Taylor Hall ; Phone: ;
Office Hours: MTW 8: :00 am;
Th, F 9: :00 am 1:00 - 2:00 pm.
December 19, 2014: Test 1 (Chapters 12-13)
January 26 , 2015: Test 2 (Chapters 14-16)
February 13, 2015: Test 3 (Chapters 17-19)
March 2, 2015: Test 4 (Chapters 20-22)
March 3 , 2015: Make Up Exam: Chapters 12-22)
Bring Scantron Sheet 882-E
CHEM 121 Winter 2015

2. Chapter 18 and GHW#8 Questions & Slides
Carbohydrates
CHEM 121 Winter 2013

3. Chapter 18: Carbohydrates
18.1 Biochemistry-An Overview, 593
18.2 Occurrence and Functions of Carbohydrates, 593
18.3 Classification of Carbohydrates, 594
18.4 Chirality: Handedness in Molecules, 595
18.5 Stereoisomerism: Enantiomers and Diastereomers, 599
18.6 Designating Handedness Using Fischer Projection Formulas, 600
18.7 Properties of Enantiomers, 604
18.8 Classification of Monosaccharides, 607
18.9 Biochemically Important Monosaccharides, 609
18.10 Cyclic Forms of Monosaccharides, 612
18.11 Haworth Projection Formulas, 615
18.12 Reactions of Monosaccharides, 618
18.13 Disaccharides, 621
18.14 Oligosaccharides, 631
18.15 General Characteristics of Polysaccharides, 634
18.16 Storage Polysaccharides, 635
18.17 Structural Polysaccharides, 637
18.18 Acidic Polysaccharides, 640
18.19 Dietary Considerations and Carbohydrates, 641 33
CHEM 121 Winter 2013

4. Carbohydrates
Organic compounds containing many -OH groups (polyhydroxy), and aldehydes or ketones functional groups. They are called sugars.
Aldoses: Aldehyde sugars are called aldoses.
Ketoses: Ketone sugars are called ketoses.
Formula for Cabohydrates:
CnH2nOn or Cn(H2O)n (hydrates of C)
n= number of atoms
Monosaccharides
They consist of one sugar containing 3,4,5,6 and 7 carbon atoms  
Disaccharides
Polysaccharides
CHEM 121 Winter 2013

5. Drawing Sugar Molecules
Linear structure-Fischer projection
Aldehyde
Ketone
hydroxy
Polyhydroxy
aldehyde
Polyhydroxy ketone
CHEM 121 Winter 2013

6. Types of sugars Number fo carbon atoms
Triose sugar units containing three carbon atoms
Tetroses sugar units containing four carbon tomsa
Pentoses sugar units containing five carbon atoms
Hexoses sugar units containing six carbon atoms
CHEM 121 Winter 2013

7. CHEM 121 Winter 2013

8. Chirality: Handedness in Molecules
Most monosaccharaides exist in two forms: a “left handed” and “right handed” form due to chiral carbon atoms
L isomers
D isomers
CHEM 121 Winter 2013

9. Chirality and Optical Activity
L isomers
D isomers
Polarimeter assigns D and L isomers
D-rotated to right
L-rotates to left
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10. Cyclic anomeric forms: a- and b- forms
Fischer structure
Haworth structures
ALDEHYDE sugar or aldoses  + alcohol  --- hemiacetal (cyclic ring)
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11. 1) Give names of the following carbohydrates
1) Give names of the following carbohydrates. Identify the chiral carbon atoms with *
CHEM 121 Winter 2013

12. 2) Circle the correct classifications that apply to the following carbohydrates.
CHEM 121 Winter 2013

13. 2) Circle the correct classifications that apply to the following carbohydrates.
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14. 2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses.
CHEM 121 Winter 2013

15. 2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses.
CHEM 121 Winter 2013

16. 2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses.
CHEM 121 Winter 2013

17. 2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses.
CHEM 121 Winter 2013

18. How you get cyclic hemiacetal form of the ketohexose sugar D-fructofuranose with b-anomeric.
CHEM 121 Winter 2013

19. How you get cyclic hemiacetal form of the ketohexose sugar D-glucopyranose with b-anomeric.
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20. 4)
a) Complete the following diagram to get the cyclic hemiacetal form of the aldohexose sugar D-glucopyranose with b-anomeric configuration.
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21. b) Draw the structure of b-D-mannopyranose4)
b) Draw the structure of b-D-mannopyranose
CHEM 121 Winter 2013

22. 4) c) What is the difference between
pynanose and furanose types of sugars?
d) What is the difference between a and b
forms of cyclic hemiacetal forms of sugars?
CHEM 121 Winter 2013

23. 5) Convert the hemiacetal cyclic structures (Haworth Projections) for following carbohydrates to Fischer Projections.
a) Use the procedure we used in problem 4 to get linear form of the hexoketose sugar from cyclic D-fructofuranose with a-anomeric
CHEM 121 Winter 2013

24. 5)
b) Use the procedure we used in problem 4 to get linear form of the hexoaldose sugar from cyclic D-sugarpyranose with b-anomeric
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25. Glycosidic bonds
Glycosidic bond- covalent bond between a hemiacetal or hemiketal and an alcohol.
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26. 6) What are the following? What is/are glucosidic linkage found in them?
a) Starch:
b) Amylopectin:
c) Glycogen:
d) Cellulose
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27. a) Name of the following o-glucoside
7) Answer following question about glycosidic bond of the di-, oligo- and poly- saccharides.
a) Name of the following o-glucoside
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28. b) Name of the following N-Glycoside8)
b) Name of the following N-Glycoside
c) Name of the following glucoside.
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29. 8)
d) The following is a part of a cellulose polymeric chain. What is the type of glucosidic linkage?
CHEM 121 Winter 2013

30. Nucleic Acids phosphate-group+pentose-sugar+Base
D-Ribose D-deoxyribose
Deoxysugar or D-deoxyribose: ribose-derivative with an oxygen missing on C-2.
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31. Nucleic Acids
Bases
Purines
pyrimidines
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32. e) What is DNA? Describe the components.8)
e) What is DNA? Describe the components.
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33. 8)
f) What is RNA? Describe the components.
CHEM 121 Winter 2013