1. Enrichment Assignment
Western School of Health and Business Careers
Introduction to Chemistry
Basic Concepts of Organic Chemistry
Common Organic Molecules
Medicinal Chemistry and the
Chemistry of Drugs
August 27, 2005
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2. The majority of this presentation was taken from Karen Timberlake at: Some slides and most learning checks were adapted as appropriate for this course by Jolene Spadafora

3. Alkanes and Aromatic Hydrocarbons
Organic Compounds
Bonding in Hydrocarbons
Naming Alkanes
Properties of Alkanes

4. Organic Compounds Contain carbon Have covalent bonds
Have low melting points
Have low boiling points
Burn in air (oxygen)
Are soluble in nonpolar solvents
Form large molecules

5. Alkanes Contain C and H only Contain single bonds C-C
Have 4 bonds to every carbon (C) atom
This is called a saturated hydrocarbon

6. Complete Structural Formulas
Show the bonds between each of the atoms
H H
 
H  C  H H C H
CH4 , methane
In methane, CH4 the four valence electrons of carbon are shared with the single electrons of four hydrogen (H) atoms. Each pair of electrons is a single bond, which can be drawn as a line. When a structure is drawn to show each bond, it is called a complete structural formula.

7. More Alkanes H H Condensed Structural Formulas H C C H CH3 CH3
H H Ethane
H H H
H C C C H CH3 CH2 CH3
H H H Propane
The complete structural formula for ethane shows the single bonds between two carbon atoms and six H atoms. The complete structural formula of propane shows the 3-carbon chain with single bonds to the attached H atoms. To write a condensed structural formula, the H atoms are written as a group next to their respective C atoms.

8. IUPAC Names IUPAC stands for: International Union of Pure and Applied Chemistry
Name # carbons Structural Formula
Methane 1 CH4
Ethane 2 CH3CH3
Propane 3 CH3CH2CH3
Butane 4 CH3CH2CH2CH3
Pentane 5 CH3CH2CH2CH2CH3
Octane
The names of organic compounds are determined by the IUPAC rules (International Union of Pure and Applied Chemistry). The stem of the name states the number of carbon atoms in the carbon chain of the compounds. The suffix, in this case –ane, indicates the alkane family.

9. IUPAC NAMES Hexane 6 CH3CH2CH2CH2CH2CH3
Name # carbons Structural Formula
Hexane CH3CH2CH2CH2CH2CH3
Heptane CH3CH2CH2CH2CH2CH2CH3
Octane CH3CH2CH2CH2CH2CH2CH2CH3
Nonane CH3 CH2 CH2CH2CH2CH2CH2CH2CH3
Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

10. STOP! Learning Check #1 What is an organic compound?
2. What is an alkane?
3. What is the name of the alkane that contains 3 carbons?

11. STOP! Learning Check #1 4. What is the condensed formula for H H H H
H C C C C H
5. What is its molecular formula?
6. What is its name?

12. Reactions of Alkanes
Combustion
alkane + O CO2 + H2O + heat

13. Combustion In the Cell Metabolic oxidation is combustion
C6H12 O6 + 6O CO2 + 6H2O + heat
glucose

14. STOP! Learning Check #2 C3H8 + O2 + Balance your equation
Complete the combustion reaction for propane
C3H8 + O
Balance your equation

15. Alkanes and Aromatic Hydrocarbons
Cycloalkanes
Aromatic Hydrocarbons

16. Each corner or point on a ring represents a carbon atom!
Cycloalkanes
Cyclopropane CH2
CH CH2
Cyclobutane CH CH2
The is a group of alkanes that have a cyclic structure. These cycloalkanes contain a carbon chain that is in a ring. Each cycloalkane has a formula that is 2C less than the corresponding alkane. For example, propane is C3H8 whereas cyclopropane ic C3H6. Butane is C4H10 and cyclobutane is C4H10. The names of the cyclic structures use the prefix cyclo in from of the alkane name for the carbon chain.
Each corner or point on a ring
represents a carbon atom!

17. More Cycloalkanes
Cyclopentane CH2
CH CH2
CH CH2
Cyclohexane
CH2

18. Aromatic Compounds and Benzene
Aromatic compounds contain benzene.
Benzene, C6H6 , is represented as a six carbon ring with 3 double bonds.
Two possible can be drawn to show benzene in this form.

19. Benzene Structure
The structures for benzene can also be written as a single structure where the alternating double bonds are written as a circle within the ring.
Benzene
structure

20. Aromatic Compounds in Nature and Health
Many aromatic compounds are common in nature and in medicine.

21. STOP! Learning Check #3 What is the name of this molecule:
2. How many carbon atoms are present in:
What is the difference between benzene and
cyclohexane?
4. Draw 2 structures that show the two different
ways benzene can be drawn.
List two drugs that contain a benzene ring in
their chemical structure.

22. Haloalkanes, Alkenes, and Alkynes
Functional Groups
Haloalkanes
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Hi !
My name
is Dana

23. * Functional Groups *
Part of an organic molecule where chemical reactions take place
Composed of an atom or group of atoms
Replace a H in the corresponding alkane
Provide a way to classify organic compounds

24. Some Types of Functional Groups
Haloalkane -F, -Cl, -Br CH3Cl
Alcohol -OH CH3OH
Ether -O- CH3-O-CH3
Aldehyde
Ketone

25. More Functional Groups
Carboxylic acid -COOH CH3COOH
Ester COO- CH3COOCH3
Amine NH2 CH3NH2
Amide -CONH2 CH3CONH2

26. Haloalkanes
An alkane in which one or more H atoms is replaced with a halogen (F, Cl, Br, or I)
CH3Br 1-bromomethane
Br (methyl bromide)
CH3CH2CHCH3 2-bromobutane Cl
chlorocyclobutane

27. Haloalkanes as Anesthetics
Halothane (Fluothane)
F Cl
F C C Br
F H
Fluothane is a haloalkane that is widely used as an anesthetic, which is a compound that decreases the ability of the nerve cells to conduct pain.

28. Ozone Layer
Ozone layer
Stratosphere
(10-30 miles
Above Earth)

29. Chlorofuorocarbons (CFCs)and the Ozone Layer
ozone O3 layer absorbs most of the sun’s harmful radiation.
CFCs - chlorofluorocarbons - are depleting that ozone layer.
CFCs are used as Freons in refrigeration,
air conditioning, and foam insulation.
Their use in spray cans is no longer allowed.

30. Chlorofuorocarbons and the Ozone Layer
In the stratosphere, the CFCs react with
the high-energy UV radiation from the sun
UV light
CF2Cl CF2Cl + Cl
Freon free radical

31. Chlorofuorocarbons and the Ozone Layer
To become stable, the Cl acquires an electron from ozone O3 and produces ClO.
Cl O3 ClO + O2
The presence of ClO in the atmosphere is an indicator of the disappearance of ozone.

32. Impact of Loss of Ozone Layer
According to the National Academy of
Sciences, each 1% loss of ozone increases
by 2% the amount of UV radiation reaching
the earth. More UV radiation means more
skin cancer and cataracts in humans, more
intense photochemical smog, and lower crop
yields.

33. STOP! Learning Check #4 What is a haloalkane?
1. What is a functional group?
What is a haloalkane?
What is a medicinal use of a haloalkane?
4. Which compounds deplete the ozone layer?
5. Where do we find these compounds?
List 3 effects of depleting the ozone layer.

34. Alcohols, Phenols, Ethers, Aldehydes, and Ketones
Alcohols, Phenols, and Thiols
Ethers
Reactions of Alcohols

35. Compounds with Oxygen Atoms
Alcohols -OH hydroxyl CH3-OH
CH3CH2-OH
Phenols
Ethers -O CH3-O-CH3

36. STOP! Learning Check #5
Classify each as an alcohol (1), phenol (2), or an ether (3):
A. _____ CH3CH2-O-CH3 C. _____ CH3CH2OH
B. _____

37. Naming Alcohols A carbon compound that contain -OH (hydroxyl) group
In IUPAC name, the -e in alkane name is replaced with -ol.
CH4 methane
CH3OH methanol (methyl alcohol)
CH3CH3 ethane
CH3CH2OH ethanol (ethyl alcohol)

38. Ethanol CH3CH2OH Acts as a depressant
Kills or disables more people than any other drug
12-15 mg/dL ethanol metabolized by a social drinkers in one hour
30 mg/dL ethanol metabolized by an alcoholic in one hour.

39. Alcohol in Some Products
% Ethanol Product
50% Whiskey, rum, brandy
40% Flavoring extracts
15-25% Listerine, Nyquil, Scope
12% Wine, Dristan, Cepacol
3-9% Beer, Lavoris

40. Some Typical Alcohols “rubbing alcohol” CH3CHCH3 (isopropyl alcohol)
antifreeze HO-CH2-CH2-OH
(ethylene glycol)
glycerol HO-CH2-CH-CH2OH
Anti-freeze

41. Phenols in Medicine

42. STOP! Learning Check #6
1. Which alcohol kills or disables more than any other drug?
What the formula for this drug? Circle the alcohol functional group in the formula.
3. What is the chemical name for :
a) rubbing alcohol? b) antifreeze?
4. What is a medicinal use of phenols?
5. Which over-the-counter items in a pharmacy contain the highest percentage of alcohol?

43. Thiols Contain the functional group -SH
Named by adding thiol to the name of the longest carbon chain
Number the -SH group in longer chains
CH3-SH methanethiol
CH3-CH2SH ethanethiol SH
CH3-CH-CH3 2-propanethiol

44. Thiols: - SH Group Many thiols have disagreeable odors
Used to detect gas leak
Found in onions, oysters, garlic and oysters
Onions CH3CH2CH2-SH 1-propanethiol
Garlic CH2= CHCH2-SH 2-propene-1-thiol
Skunk spray
CH trans-2-butene-1-thiol
CH = CH
CH2SH

45. Ethers Contain an -O- between two carbon groups
Simple ethers named from -yl names of the attached groups and adding ether.
CH3-O-CH3 dimethyl ether
CH3-O-CH2CH3 ethyl methyl ether

46. Ethers as Anesthetics Anesthetics inhibit pain signals to the brain
CH3CH2-O-CH2CH3 used for over a century (Diethyl Ether)
Causes nausea and is highly flammable
1960s developed nonflammable anesthetics
Cl F F Cl F H
H-C-C-O-C-H H-C-C-O-C-H
F F F H F H
Ethane(enflurane) Penthrane

47. MTBE CH3 Methyl tert-butyl ether CH3-O-C-CH3
Second in production or organic chemicals
Additive to improve gasoline performance
Use in question with discovery of contaminated water supplies

48. Reactions of Alcohols Combustion CH3OH + 2O2 CO2 + 2H2O + Heat
Dehydration
H OH
H+, heat
H-C-C-H H-C=C-H + H2O
H H H H
alcohol alkene

49. STOP! Learning Check #7 Name three thiol smells.
1. Why are thiols easy to detect?
Name three thiol smells.
3. What is an ether group?
4. What is a medicinal use of diethyl ether?
List 2 reasons diethyl ether is not used anymore.
Draw the condensed structure for diethyl ether.

50. Alcohols, Phenols, Ethers, Aldehydes, and Ketones

51. Aldehydes and Ketones O carbonyl group
In an aldehyde, an H atom is attached to a carbonyl group (C=O)
O carbonyl group 
CH3-C-H
In a ketone, two carbon groups are attached to a carbonyl group
CH3-C-CH3

52. Naming Aldehydes O O O    H-C-H CH3-C-H CH3CH2C-H
  
H-C-H CH3-C-H CH3CH2C-H
methanal ethanal propanal
(formaldehyde) (acetaldehyde) (propionaldehyde)

53. Aldehydes as Flavorings

54. Glucose is an aldehyde

55. Ketones O O   Butter flavor CH3-C-C-CH3 butanedione O 
Clove flavor CH3-C-CH2CH2CH2CH2CH3
2-heptanone

56. Fructose is a Ketone

57. Ketones as Hormones

58. STOP! Learning Check #8
1. Classify each as an aldehyde (1), ketone (2) or neither (3). O 
A. CH3CH2CCH3 B. CH3-O-CH3
CH3 O
C. CH3-C-CH2CH D.
CH3

59. STOP! Learning Check #8
2. What is the more common name of the aldehyde: methanal? Draw it’s structure.
3. What is a common use of aldehydes in the food industry?
4. Give three examples of aldehydes used for this purpose and their characteristic quality.
List two uses of ketones in the food industry.
6. Name a common sugar that is:
a) an aldehyde and b) a ketone
7. Name a hormone that is a ketone.

60. Carboxylic Acids, Esters, Amines and Amides
Properties of Carboxylic Acids
Esters
Esterification and Hydrolysis
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61. Carboxyl Group
Carboxylic acids contain the carboxyl group on carbon 1. O 
CH3 — C—OH = CH3—COOH
carboxyl group

62. Naming Carboxylic Acids
Formula IUPAC Common
alkan -oic acid prefix – ic acid
HCOOH methanoic acid formic acid
CH3COOH ethanoic acid acetic acid
CH3CH2COOH propanoic acid propionic acid
CH3CH2CH2COOH butanoic acid butyric acid

63. Esters
In and ester, the H in the carboxyl group is replaced with an alkyl group O 
CH3 — C—O —CH3 = CH3—COO —CH3
ester group

64. Esters in Plants
Esters give flowers and fruits their pleasant fragances and flavors.

65. Some Esters and Their Names
Flavor/Odor
Raspberries
HCOOCH2CH3 ethyl methanoate (IUPAC)
ethyl formate (common)
Pineapples
CH3CH2CH2 COOCH2CH3
ethyl butanoate (IUPAC)
ethyl butyrate (common)

66. STOP! Learning Check #9 What is a carboxyl group?
What is the formula for the carboxylic acid: acetic acid?
What is a pleasant quality of esters?

67. Carboxylic Acids Esters, Amines and Amides
Reactions of Amines
Amides
Reactions of Amides

68. Amines Organic compounds of nitrogen N
Classified as primary, secondary, tertiary
CH CH3
 
CH3—NH2 CH3—NH CH3—N — CH3
1° 2° °

69. Alkaloids Physiologically active nitrogen-containing compounds
Obtained from plants
Used as anesthetics, antidepressants, and stimulants
Many are addictive

70. Nicotine

71. Caffeine

72. Procaine

73. Amides
Derivatives of carboxylic acids where an amino (-NH2) group replaces the –OH group.
O O
 
CH3 — C—OH CH3 — C—NH2
carboxylic acid amide
acetic acid acetamide

74. Aromatic Amides

75. STOP! Learning Check #10 What is an amine? What is an alkaloid?
What are three positive effects of alkaloids?
What is a negative effect of alkaloids?
Name three alkaloids.

76. Structures of Important Monosaccharides
Carbohydrates
Classification
Monosaccharides
Structures of Important Monosaccharides
Cyclic Structures

77. Carbohydrates Major source of energy from our diet
A molecule Composed of the elements C, H and O
Produced by photosynthesis in plants

78. Types of Carbohydrates
Monosaccharides
Disaccharides
Contain 2 monosaccharide units
Polysaccharides
Contain many monosaccharide units

79. Monosaccharides Three Carbons = Triose Four Carbons = Tetrose
Five Carbons = Pentose
Six Carbons = Hexose

80. Monosaccharides
Aldoses are Monosaccharides with an aldehyde group and many hydroxyl (-OH) groups.
Ketoses are Monosaccharides with a ketone group and many hydroxyl (-OH) groups.

81. aldose, hexose ketose, pentose

82. Glucose

83. Fructose

84. Galactose
D-galactose

85. Cyclic Structures
Monosaccharides with 5-6 carbon atoms form cyclic structures
The hydroxyl group on C-5 reacts with the aldehyde group or ketone group

86. Haworth Structure for D-Glucose 
-D-Glucose -D-Glucose

87. STOP! Learning Check #11
What is a carbohydrate?
Name 3 common Monosaccharides and draw their chemical structures.

88. Carbohydrates
Disaccharides
Polysaccharides

89. Important Disaccharides
Maltose = Glucose + Glucose
Lactose = Glucose + Galactose
Sucrose = Glucose + Fructose

90. Maltose 
 -1,4-glycosidic bond
- D-Maltose

91. Lactose
 -1,4-glycosidic bond
α-D-Lactose 

92. Sucrose
α, -1,2-
glycosidic bond
C12 H22 O11
Table Sugar!

93. Polysaccharides
Starch
Amylose
Amylopectin
Glycogen
Cellulose

94. Polysaccharides
Polymers of D-Glucose

95. Amylose
Polymer with α-1,4 bonds
α-1,4 bonds

96. Amylopectin α-1,6 bond Polymer with α-1,4 and α-1,6 bonds branches

97. Cellulose
Polymer with ß-1,4 bonds
ß-1,4 bonds

98. STOP! Learning Check #12
1. Identify the monosaccharides in each of the
following disaccharides:
A. lactose
(1) glucose (2) fructose (3) galactose
B. maltose
(1) glucose (2) fructose (3) galactose
C. sucrose
2. Name 3 Polysaccharides.

99. Chemical Properties of Triglycerides
Lipids
Types of Lipids
Fatty Acids
Fats, and Oils
Chemical Properties of Triglycerides

100. Types of Lipids Lipids with fatty acids Waxes
Fats and oils (trigycerides)
Phospholipids
Sphingolipids
Lipids without fatty acids
Steroids

101. Fatty Acids Long-chain carboxylic acids Insoluble in water
Typically carbon atoms (even number)
Some contain double bonds
corn oil contains 86% unsaturated fatty acids and 14% saturated fatty acids

102. Saturated and Unsaturated Fatty Acids
Saturated = C–C bonds
Unsaturated = one or more C=C bonds

103. Structures Saturated fatty acids Fit closely in regular pattern
Unsaturated fatty acids
Cis double bonds

104. Properties of Saturated Fatty Acids
Contain only single C–C bonds
Closely packed
Strong attractions between chains
High melting points
Solids at room temperature

105. Properties of Unsaturated Fatty Acids
Contain one or more double C=C bonds
Nonlinear chains do not allow molecules to pack closely
Few interactions between chains
Low melting points
Liquids at room temperature

106. STOP! Learning Check #13 What is a fatty acid?
What is the difference between saturated and unsaturated?
Based on the properties of saturated fatty acids, name some saturated fatty acids.
4. Based on the properties of unsaturated fatty acids, name some unsaturated fatty acids or fatty acids that must be at least mostly unsaturated.

107. Steroids Steroid nucleus 3 cyclohexane rings 1 cyclopentane ring

108. Cholesterol Most abundant steroid in the body
Add methyl CH3- groups, alkyl chain, and -OH to steroid nucleus

109. Cholesterol in the Body
Cellular membranes
Myelin sheath, brain, and nerve tissue
Bile salts
Hormones
Vitamin D

110. Bile Salts Synthesized in the liver from cholesterol
Stored in the gallbladder
Secreted into small intestine
Mix with fats to break them part
Emsulsify fat particles

111. Example of a Bile Salt

112. Steroid Hormones Chemical messengers in cells Sex hormones
Androgens in males (testosterone)
Estrogens in females (estradiol)
Adrenocorticosteroids from adrenal glands
mineralocorticoids (electrolyte balance)
glucocorticoids regulate glucose level

113. Sex Hormones

114. STOP! Learning Check #14
What is the most abundant steroid in the body?
What do bile salts do?
What are the names of the male and female sex hormones?
4. What is/are the difference(s) in the chemical structures of these two hormones?