Transcript to Dowload Part 1: PowerPoint Presentation.

Enrichment Assignment
Western School of Health and
Business Careers
Introduction to Chemistry
* Basic Concepts of Organic Chemistry
* Common Organic Molecules
* Medicinal Chemistry and the
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Chemistry of Drugs
August 27, 2005
The majority of this presentation
was taken from Karen
Timberlake at:
http://www.karentimberlake.com/chemodul.html
Some slides and most learning checks were adapted as
appropriate for this course by
Jolene Spadafora
Alkanes and Aromatic Hydrocarbons
Organic Compounds
Bonding in Hydrocarbons
Naming Alkanes
Properties of Alkanes
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
Alkanes
 Contain
C and H only
 Contain
single bonds C-C
 Have
 This
4 bonds to every carbon (C) atom
is called a saturated hydrocarbon
Complete Structural Formulas
Show the bonds between each of the
atoms
H
H

HCH
H
C

H
H
CH4 , methane
H
More Alkanes
H
H
H
H
C
C
H
H
Condensed Structural Formulas
H
CH3
CH3
Ethane
H
H
H
C
C
C
H
H
H
H
CH3 CH2 CH3
Propane
IUPAC Names
IUPAC stands for: International Union of Pure and Applied Chemistry
Name
# carbons
Structural Formula
Methane 1
CH4
Ethane
CH3CH3
2
Propane 3
CH3CH2CH3
Butane
CH3CH2CH2CH3
4
Pentane 5
CH3CH2CH2CH2CH3
Octane
IUPAC NAMES
Name # carbons
Structural Formula
Hexane 6
CH3CH2CH2CH2CH2CH3
Heptane 7
CH3CH2CH2CH2CH2CH2CH3
Octane
8
CH3CH2CH2CH2CH2CH2CH2CH3
Nonane 9
CH3 CH2 CH2CH2CH2CH2CH2CH2CH3
Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
STOP! Learning Check #1
1.What is an organic compound?
2. What is an alkane?
3. What is the name of the alkane that
contains 3 carbons?
STOP! Learning Check #1
4. What is the condensed formula for
H H H H
H
C
C
C
C
H
H
H H
H
5. What is its molecular formula?
6. What is its name?
Reactions of Alkanes
Combustion
alkane + O2
CO2 + H2O + heat
Combustion In the Cell
Metabolic oxidation is combustion
C6H12 O6 + 6O2
glucose
6CO2 + 6H2O + heat
STOP! Learning Check #2
Complete the combustion reaction for propane
C 3H 8 + O 2
Balance your equation
+
Alkanes and Aromatic
Hydrocarbons
Cycloalkanes
Aromatic Hydrocarbons
Cycloalkanes
Cyclopropane
CH2
CH2
CH2
Cyclobutane
Each corner or point on a ring
represents a carbon atom!
CH2
CH2
CH2
CH2
More Cycloalkanes
Cyclopentane
CH2
CH2
CH2
CH2
CH2
Cyclohexane
CH2
CH2 CH2
CH2
CH2
CH2
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.
H
H
H
H
H
H
H
H
H
H
H
H
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
Aromatic Compounds in Nature and
Health
Many aromatic compounds are common in nature
and in medicine.
CHO
COOH
COOCH3
CH3
CH3
CH3CHCH2
CHCOOH
OCH3
OH
Aspirin
Vanillin
Ibuprofen
STOP! Learning Check #3
1. What is the name of this molecule:
2. How many carbon atoms are present in:
3. What is the difference between benzene and
cyclohexane?
4. Draw 2 structures that show the two different
ways benzene can be drawn.
5. List two drugs that contain a benzene ring in
their chemical structure.
Haloalkanes, Alkenes, and Alkynes
Functional Groups
Haloalkanes
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Hi !
My name
is Dana
* 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
Some Types of Functional Groups
Haloalkane
Alcohol
-F, -Cl, -Br CH3Cl
-OH
CH3OH
Ether
-OO
CH3-O-CH3
Aldehyde
C H
CH3CH
Ketone
O
O
C
CH3CCH3
O
More Functional Groups
Carboxylic acid -COOH
CH3COOH
Ester
-COO-
CH3COOCH3
Amine
-NH2
CH3NH2
Amide
-CONH2
CH3CONH2
Haloalkanes
An alkane in which one or more H atoms is
replaced with a halogen (F, Cl, Br, or I)
CH3Br
1-bromomethane
(methyl bromide)
Br
CH3CH2CHCH3
2-bromobutane
Cl
chlorocyclobutane
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.
Ozone Layer
Ozone layer
Stratosphere
(10-30 miles
Above Earth)
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.
Chlorofuorocarbons and the
Ozone Layer
In the stratosphere, the CFCs react with
the high-energy UV radiation from the sun
CF2Cl2
Freon-12
UV light
CF2Cl + Cl
free radical
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.
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.
STOP! Learning Check #4
1. What is a functional group?
2. What is a haloalkane?
3. What is a medicinal use of a haloalkane?
4. Which compounds deplete the ozone layer?
5. Where do we find these compounds?
6. List 3 effects of depleting the ozone layer.
Alcohols, Phenols, Ethers,
Aldehydes, and Ketones
Alcohols, Phenols, and Thiols
Ethers
Reactions of Alcohols
Compounds with Oxygen
Atoms
Alcohols -OH hydroxyl
CH3-OH
CH3CH2-OH
OH
OH
Phenols
Ethers
-O-
CH3-O-CH3
STOP! Learning Check #5
Classify each as an alcohol (1), phenol (2), or
an ether (3):
A. _____ CH3CH2-O-CH3
OH
B. _____
CH3
C. _____ CH3CH2OH
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)
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.
Alcohol in Some Products
% Ethanol
Product
50%
40%
15-25%
12%
3-9%
Whiskey, rum, brandy
Flavoring extracts
Listerine, Nyquil, Scope
Wine, Dristan, Cepacol
Beer, Lavoris
Some Typical Alcohols
OH
“rubbing alcohol”
CH3CHCH3
(isopropyl alcohol)
antifreeze
HO-CH2-CH2-OH
(ethylene glycol)
OH
glycerol HO-CH2-CH-CH2OH
Phenols in Medicine
OH
OH
OH
OH
OH
CH2CH2CH2CH2CH2CH3
Phenol
Resorcinol
(antiseptic)
4-Hexylresorcinal
(antiseptic)
STOP! Learning Check #6
1. Which alcohol kills or disables more than any
other drug?
2. 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?
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
Thiols: - SH Group
 Many thiols have disagreeable odors
 Used to detect gas leak
 Found in onions, oysters, garlic and oysters
Onions CH3CH2CH2-SH
Garlic CH2= CHCH2-SH
Skunk spray
CH3
CH = CH
1-propanethiol
2-propene-1-thiol
trans-2-butene-1-thiol
CH2SH
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
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
F F
F
Ethane(enflurane)
H-C-C-O-C-H
HF
H
Penthrane
MTBE
 Methyl tert-butyl ether
CH3
CH3-O-C-CH3
CH3
 Second in production or organic chemicals
 Additive to improve gasoline performance
 Use in question with discovery of contaminated
water supplies
Reactions of Alcohols
Combustion
CH3OH + 2O2
CO2 + 2H2O + Heat
Dehydration
H OH
H-C-C-H
H+, heat
H-C=C-H + H2O
H H
alcohol
H H
alkene
STOP! Learning Check #7
1. Why are thiols easy to detect?
2. Name three thiol smells.
3. What is an ether group?
4. What is a medicinal use of diethyl ether?
5. List 2 reasons diethyl ether is not used anymore.
6. Draw the condensed structure for diethyl ether.
Alcohols, Phenols, Ethers,
Aldehydes, and Ketones
Aldehydes and Ketones
Aldehydes and Ketones
 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
O

CH3-C-CH3
carbonyl group
Naming Aldehydes
O

H-C-H
methanal
O

CH3-C-H
ethanal
O

CH3CH2C-H
propanal
(formaldehyde) (acetaldehyde) (propionaldehyde)
Aldehydes as Flavorings
O
O
CH
CH
O
CH=CH CH
HO
OCH3
Benzaldehyde
(almonds)
Vanillin
(vanilla beans)
Cinnamaldehyde
(cinnamon)
Glucose is an aldehyde
O
H
C
H C OH
HO C H
H C OH
H C OH
CH 2OH
glucose
Ketones
OO

Butter flavor
CH3-C-C-CH3
O
butanedione

Clove flavor
CH3-C-CH2CH2CH2CH2CH3
2-heptanone
Fructose is a Ketone
CH 2OH
C
HO
O
C H
H
C
OH
H
C
OH
CH 2OH
D-Fructose
Ketones as Hormones
CH2OH
O
CH3
O
OH
CH3
O
Cortisone
STOP! Learning Check #8
1. Classify each as an aldehyde (1), ketone
(2) or neither (3).
O

A. CH3CH2CCH3
CH3
O
O

C. CH3-C-CH2CH
CH3
B. CH3-O-CH3
D.
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.
5. 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.
Carboxylic Acids, Esters, Amines and Amides
Carboxylic Acids
Properties of Carboxylic Acids
Esters
Esterification and Hydrolysis
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
Carboxyl Group
Carboxylic acids contain the carboxyl group
on carbon 1.
O

CH3 — C—OH =
CH3—COOH
carboxyl group
Naming Carboxylic Acids
Formula
IUPAC
alkan -oic acid
Common
prefix – ic acid
HCOOH
methanoic acid
formic acid
CH3COOH
ethanoic acid
acetic acid
CH3CH2COOH
propanoic acid
propionic acid
CH3CH2CH2COOH butanoic acid
butyric acid
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
Esters in Plants
Esters give flowers and fruits their
pleasant fragances and flavors.
Some Esters and Their Names
Flavor/Odor
Raspberries
HCOOCH2CH3
ethyl methanoate (IUPAC)
ethyl formate (common)
Pineapples
CH3CH2CH2 COOCH2CH3
ethyl butanoate (IUPAC)
ethyl butyrate (common)
STOP! Learning Check #9
1.What is a carboxyl group?
2.What is the formula for the
carboxylic acid: acetic acid?
3.What is a pleasant quality of
esters?
Carboxylic Acids Esters, Amines and Amides
Amines
Reactions of Amines
Amides
Reactions of Amides
Amines
• Organic compounds of nitrogen N
• Classified as primary, secondary, tertiary
CH3
CH3


CH3—NH2 CH3—NH CH3—N — CH3
1°
2°
3°
Alkaloids
• Physiologically active nitrogen-containing
compounds
• Obtained from plants
• Used as anesthetics, antidepressants, and
stimulants
• Many are addictive
Nicotine
CH3
N
Nicotine, leaves of tobacco plant
Caffeine
O
CH3
O
CH3
N
N
N
N
CH3
Caf f e in e , cof f e e b e an s an d t e a
Procaine
CH3CH2
O
N
CH2CH2 O C
NH2
CH3CH2
Procaine (novocaine), painkiller
Amides
Derivatives of carboxylic acids where an
amino (-NH2) group replaces the –OH
group.
O
O


CH3 — C—OH
carboxylic acid
acetic acid
CH3 — C—NH2
amide
acetamide
Aromatic Amides
O
O
C NH2
C NHCH3
Benzamide
N -methylbenzamide
STOP! Learning Check #10
1. What is an amine?
2. What is an alkaloid?
3. What are three positive effects of alkaloids?
4. What is a negative effect of alkaloids?
5. Name three alkaloids.
Carbohydrates
Classification
Monosaccharides
Structures of Important
Monosaccharides
Cyclic Structures
Carbohydrates
• Major source of energy from our diet
• A molecule Composed of the elements
C, H and O
• Produced by photosynthesis in plants
Types of Carbohydrates
• Monosaccharides
• Disaccharides
Contain 2 monosaccharide units
• Polysaccharides
Contain many monosaccharide units
Monosaccharides
• Three Carbons =
Triose
• Four Carbons =
Tetrose
• Five Carbons =
Pentose
• Six Carbons =
Hexose
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.
H
C O
H C OH
H C OH
H C OH
CH2OH
C O
HO C H
H C OH
H C OH
CH 2OH
CH2OH
aldose, hexose
ketose, pentose
Glucose
H
C O
H C OH
HO C H
H C OH
H C OH
CH 2OH
D-Glucose
Fructose
CH 2OH
C O
HO C H
H C OH
H C OH
CH 2OH
D-Fructose
Galactose
H
O
C
H C OH
HO C H
HO C H
H C OH
CH 2OH
D-galactose
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
o
O
Haworth Structure for D-Glucose
CH2OH
CH2OH
o
o
OH
OH

OH
OH
OH
OH
-D-Glucose

OH
OH
-D-Glucose
STOP! Learning Check #11
1. What is a carbohydrate?
2. Name 3 common Monosaccharides
and draw their chemical structures.
Carbohydrates
Disaccharides
Polysaccharides
Important Disaccharides
• Maltose
= Glucose + Glucose
• Lactose
= Glucose + Galactose
• Sucrose
= Glucose + Fructose
Maltose

CH2OH
CH2OH
O
OH
O
O
OH
OH
OH
OH
 -1,4-glycosidic bond
- D-Maltose
OH
Lactose
CH2OH
O
CH2OH
O
HO
O
OH
OH
OH
OH
OH

 -1,4-glycosidic bond
α-D-Lactose
Sucrose
CH 2OH
o
OH
α, -1,2-
OH
glycosidic bond
OH
CH 2OH
O
C12 H22 O11
O
OH
OH
CH 2OH
Table Sugar!
Polysaccharides
• Starch
Amylose
Amylopectin
• Glycogen
• Cellulose
Polysaccharides
• Polymers of D-Glucose
CH2OH
O
OH
OH
OH
OH
Amylose
Polymer with α-1,4 bonds
CH2OH
CH2OH
O
CH2OH
O
OH
O
OH
O
O
OH
O
OH
CH2OH
OH
O
OH
O
O
OH
α-1,4 bonds
OH
Amylopectin
Polymer with α-1,4 and α-1,6 bonds branches
CH2OH
CH2OH
O
O
OH
O
OH
O
α-1,6 bond
CH2OH
OH
O
O
OH
O
OH
CH2OH
OH
CH2OH
O
CH2
O
OH
O
OH
O
α-1,4 bonds
O
OH
O
OH
CH2OH
OH
O
OH
O
O
OH
OH
Cellulose
Polymer with ß-1,4 bonds
CH2OH
O
OH
CH2OH
O
O
OH
OH
CH2OH
O
O
OH
OH
O
ß-1,4 bonds
OH
O
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
(1) glucose
(2) fructose (3) galactose
2. Name 3 Polysaccharides.
Lipids
Types of Lipids
Fatty Acids
Fats, and Oils
Chemical Properties of Triglycerides
Types of Lipids
• Lipids with fatty acids
Waxes
Fats and oils (trigycerides)
Phospholipids
Sphingolipids
• Lipids without fatty acids
Steroids
Fatty Acids
•
•
•
•
Long-chain carboxylic acids
Insoluble in water
Typically 12-18 carbon atoms (even number)
Some contain double bonds
corn oil contains 86%
unsaturated fatty acids and
14% saturated fatty acids
Saturated and Unsaturated Fatty
Acids
Saturated = C–C bonds
Unsaturated = one or more C=C bonds
COOH
palmitic acid, a saturated acid
COOH
palmitoleic acid, an unsaturated fatty acid
Structures
Saturated fatty acids
• Fit closely in regular pattern
COOH
COOH
COOH
H
H
Unsaturated fatty acids
• Cis double bonds
C C
cis double bond
COOH
Properties of Saturated Fatty Acids
• Contain only single C–C bonds
• Closely packed
• Strong attractions between chains
• High melting points
• Solids at room temperature
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
STOP! Learning Check #13
1. What is a fatty acid?
2. What is the difference between saturated and
unsaturated?
3. 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.
Steroids
• Steroid nucleus
• 3 cyclohexane rings
• 1 cyclopentane ring
steroid nucleus
Cholesterol
• Most abundant steroid in the body
• Add methyl CH3- groups, alkyl chain, and OH to steroid nucleus
CH3
CH3
CH3
CH3
CH3
HO
Cholesterol in the Body
• Cellular membranes
• Myelin sheath, brain, and nerve tissue
• Bile salts
• Hormones
• Vitamin D
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
Example of a Bile Salt
cholic acid, a bile acid
CH3
OH
CH3
CH3
HO
O
C N CH2 COO- Na+
H
gycine, an amino acid
OH
sodium glycocholate, a bile salt
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
Sex Hormones
CH3 OH
CH3
O
CH3 OH
CH3
HO
t e st ost e r on e
e st r ad iol
STOP! Learning Check #14
1. What is the most abundant steroid in the body?
2. What do bile salts do?
3. 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?