CHEM-202 TUTORIALS

IMPORTANT! Please, do all exercises for each Chapter which we study:

Click on each link for a particular Chapter, complete the exercises by following instructions, and return to this menu. Some of the applets may not work, because of a high security settings on your browser. You may want to adjust your setting temporarily. If it is still not working, try a CD version which you can obtain from Dr. Alexey Ignatchenko.

 

#

Chapter: Subject

Chapter

 

Chapter 10-11: Structure, Synthesis and Reactions of Alcohols

1

 Nomenclature of Alcohols

10

2

 Dehydration of an Unbranched Primary Alcohol to an Alkene

10

3

 Reaction of a Primary Alcohol with HCl

10

4

 Acidity and Electron Delocalization

10

5

 Grignard Reagents in Synthesis

10

6

 Nomenclature of Alcohols

10

7

 Nucleophilic Additions to Carbonyls II

10

8

 Summary of Systematic Nomenclature

10

9

 Acid-Catalyzed Substitution of a Tertiary Alcohol

11

10

 Bromination of a Primary Alcohol with Phosphorus Tribromide

11

11

 Chromic Acid Oxidation of a Secondary Alcohol

11

12

 Dehydration of a Secondary Alcohol

11

13

 Reaction of a Secondary Alcohol with Thionyl Chloride

11

14

 Changes in Oxidation State

11

15

 Leaving Groups

11

16

 Manipulating the Equilibrium

11

 

Chapter 13: NMR Spectroscopy

 

17

Interpretation of NMR spectra

13

18

13C-NMR

13

19

Chemical Shift

13

20

Equivalent Hydrogens

13

21

Hydrogen Deficiency

13

22

Integration

13

23

NMR Database

13

24

Peak Splitting

13

 

Chapter 14: Ethers, Epoxides, Thioethers

25

Nucleophilic Additions of alcohols to epoxides

14

26

Halohydrin Reaction

8, 14

27

Ring Opening of Epoxides

14

28

Organometallic Compounds Reaction with epoxides

14

29

Nomenclature of Ethers

14

30

Acid-Catalyzed Hydrolysis of an Ether

14

31

Intermolecular Dehydration of an Alcohol

14

 

Chapter 15: Conjugated Systems, Orbital Symmetry, UV Spectroscopy

32

Cycloaddition Reactions

15

33

1,2- and 1,4-Addition to a Conjugated Diene

15

34

Diels-Alder Reaction

15

 

Chapter 16: Aromatic compounds

35

Aromaticity

16

36

Aromaticity and Acidity

16

37

Basic Sites in Nitrogen Heterocycles

16

38

Donation of Electrons into a Benzene ring

16

39

Lone-Pair Electrons on Nitrogen

16

40

Molecular Orbital Description - Aromatic or not?

16

41

Recognizing Common Heterocycles

16

 

Chapter 17: Reactions of Aromatic compounds

42

Electrophilic Aromatic Substitution Definitions and Examples

17

43

Electrophilic Aromatic Substitution (continued)

17

44

Intermediates in Electrophilic substitution

17

45

Multistep Synthesis of Disubstituted aromatic compounds

17

46

The Sandmeyer Reaction

17

47

Terms for the Reactions of Substitution

17

48

Multistep Synthesis of Disubstituted benzenes

17

49

Kolbe Carboxylation of Phenol

17

50

Aromatic Nitration

17

51

Claisen Rearrangement

17

52

Electrophilic Aromatic Substitution with Cl

17

53

Friedel-Crafts Acylation

17

54

Friedel-Crafts Alkylation

17

55

Nucleophilic Aromatic Substitution

17

 

Chapter 18: Ketones and Aldehydes

56

Addition to Carbonyl Compounds

18

57

a-Halogenated Carbonyl Compounds

18

58

Halohydrin Reaction

18

59

Imine and Oxime Reactions in Synthesis

18

60

Nomenclature of Aldehydes and Ketones

18

61

Wolff-Kishner Reaction in Syntesis

18

62

Wittig Reaction Synthesis

18

63

Nomenclature of Aldehydes and Ketones

18

64

Acid-Catalyzed Alpha Halogenation of a Ketone

18

65

Acid-Catalyzed Formation of a Hemiacetal

18

66

Acid-Catalyzed Formation of an Acetal

18

67

Base-Promoted Alpha Halogenation of a Ketone

18

68

Formation of a Cyanohydrin

18

69

Formation of a Cyclic Hemiacetal

18

70

Formation of an Imine

18

71

Reduction of a Ketone by Sodium Borohydride

18

72

Wittig Reaction

18

73

Wolff-Kishner Reduction

18

74

Acid-Catalyzed Alpha Halogenation of a Ketone

 

 

Chapter 19: Amines

75

Hofmann Elimination Reaction

19

76

Synthesis of Amines

19

77

Hofmann Reaction

19

78

Nitrosyl Cation Reaction with an Amine

19

79

Reaction of a Primary Amine with Nitrous Acid

19

 

Chapter 20, 21: Carboxylic Acids and their derivatives

80

Conversions Between Carboxylic Acid Derivatives

21

81

Common Terms of Carboxylic Acid derivatives (1)

20

82

Common Terms of Carboxylic Acid Derivatives (2)

20

83

Mechanism Basic Hydrolysis of amides

21

84

Mechanism of Fischer Esterification

21

85

Fischer Esterification

21

86

Formation of a Methyl Ester with Diazomethane

21

87

Reaction of a Carboxylic Acid with Thionyl Chloride

21

88

Decarboxylation of a Beta-dicarboxylic Acid

21

89

Decarboxylation of a Beta-Ketocarboxylic Acid

21

90

Reductions

21

91

Nomenclature of Carboxylic Acids

20

92

Acid Anhydride Hydrolysis

21

93

Acid Chloride Hydrolysis

21

94

Acid Hydrolysis of a Tert-Butyl Ester

21

95

Acid Hydrolysis of an Amide

21

96

Base Hydrolysis of a Nitrile

21

97

Base Hydrolysis of an Amide

21

98

Ester Hydrolysis in Aqueous Base

21

99

Reaction of a Grignard Reagent with an Ester

21

100

Reduction of an Amide by LAH

21

101

Reduction of an Ester by Lithiumaluminumhydride

21

 

Chapter 22: Condensations and alpha substitutions of carbonyl compounds

102

 α-Proton Acidity, Enolates and Enols Formation and Reactivity

22

103

Aldol Reactions Synthesis

22

104

Enolate reactions (Video 1 enolization)

22

105

Enolate reactions (Video 2 - alkylations)

22

106

Enolate reactions (Video 3 – condensations)

22

107

Acetoacetic Ester Synthesis

22

108

Claisen Reactions Synthesis

22

109

Claisen Condensation

22

110

Common Terms for  Reactions at alpha carbon

22

111

Hints in Retrosynthetic Analysis in condensations

22

112

Malonic Ester Synthesis

22

113

Robinson Annulation Synthesis

22

114

Retrosynthesis

22

115

Acid-Catalyzed Aldol Reaction

22

116

Base-Catalyzed Aldol Reaction

22

117

Claisen Condensation

22

118

Dieckmann Condensation

22

119

Michael Reaction

22

 

Chapter 23-24: Carbohydrates, Nucleic Acids, Amino Acids, Peptides

117

Common Terms of Carbohydrates

23

118

Fischer Projections

23

119

Haworth Projections

23

120

D and L Notation

23

121

Electrophoresis and Isoelectric point

24

122

Identifying Glycosidic Linkage

23

123

Translation in mRNA

23