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

Click on me .. and I’ll sing

to you!

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 CompoundsBonding in Hydrocarbons

Naming AlkanesProperties 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 4 bonds to every carbon (C) atom

This 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 H

CH4 , methane

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

IUPAC NamesIUPAC 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

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 6CO2 + 6H2O + heat

glucose

Complete the combustion reaction for propane

C3H8 + O2 +

Balance your equation

STOP! Learning Check #2

Alkanes and Aromatic Hydrocarbons

CycloalkanesAromatic Hydrocarbons

Cycloalkanes

Cyclopropane CH2

CH2 CH2

CyclobutaneCH2 CH2

CH2 CH2Each corner or point on a ringrepresents a carbon atom!

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

HH

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.

COOH

COOCH3

CHO

OCH3

OH

Aspirin Vanillin

CHCOOH

CH3

CH3CHCH2

CH3

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 GroupsHaloalkanes

This will be you soon!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 -F, -Cl, -Br CH3Cl

Alcohol -OH CH3OH

Ether -O- CH3-O-CH3

Aldehyde

KetoneC

O

CH3CH

O

C H

O

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

Br (methyl bromide)

CH3CH2CHCH3 2-bromobutane

Cl

chlorocyclobutane

Haloalkanes as Anesthetics

Halothane (Fluothane) F Cl

F C C Br

F HFluothane 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

UV light

CF2Cl2 CF2Cl + Cl

Freon-12 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

Phenols

Ethers -O- CH3-O-CH3

OHOH

Classify each as an alcohol (1), phenol (2), or an ether (3):

A. _____ CH3CH2-O-CH3 C. _____ CH3CH2OH

B. _____

OH

CH3

STOP! Learning Check #5

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% Whiskey, rum, brandy

40% Flavoring extracts

15-25% Listerine, Nyquil, Scope

12% Wine, Dristan, Cepacol

3-9% Beer, Lavoris

Some Typical Alcohols

OH

“rubbing alcohol” CH3CHCH3

(isopropyl alcohol)

antifreeze HO-CH2-CH2-OH

(ethylene glycol)

OH

glycerol HO-CH2-CH-CH2OH

Ant

i-fre

eze

Phenols in Medicine

OH

OH

OH OH

OH

CH2CH2CH2CH2CH2CH3

Resorcinol 4-Hexylresorcinal(antiseptic) (antiseptic)

Phenol

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 chainNumber 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 odorsUsed to detect gas leakFound in onions, oysters, garlic and oysters

Onions CH3CH2CH2-SH 1-propanethiol

Garlic CH2= CHCH2-SH 2-propene-1-thiolSkunk spray

CH3 trans-2-butene-1-thiol

CH = CH

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 brainCH3CH2-O-CH2CH3 used for over a century (Diethyl

Ether)Causes nausea and is highly flammable1960s 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

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+, heat

H-C-C-H H-C=C-H + H2O

H H H H

alcohol 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 carbonyl group CH3-C-CH3

Naming Aldehydes

O O O

H-C-H CH3-C-H CH3CH2C-H

methanal ethanal propanal(formaldehyde) (acetaldehyde) (propionaldehyde)

Aldehydes as Flavorings

Benzaldehyde Vanillin Cinnamaldehyde(almonds) (vanilla beans) (cinnamon)

CH=CH CH

OCH

O

HO

OCH3

CH

O

Glucose is an aldehyde

glucose

C

OH

C

CHO H

CH OH

C

CH2OH

OH

OHH

H

Ketones

O O

Butter flavor CH3-C-C-CH3 butanedione

O Clove flavor CH3-C-CH2CH2CH2CH2CH3

2-heptanone

Fructose is a Ketone

D-Fructose

H2OHC

C

CHO H

C

O

H OH

C

CH2OH

OHH

Ketones as Hormones

Cortisone

O

CH2OH

OCH3

CH3

O OH

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

O

STOP! Learning Check #8

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 AcidsProperties of Carboxylic Acids

EstersEsterification and Hydrolysis

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song!

Carboxyl GroupCarboxylic acids contain the carboxyl group on carbon 1.

O

CH3 — C—OH = CH3—COOH

carboxyl group

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

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

AminesReactions of Amines

AmidesReactions 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

N

CH3

Nicotine, leaves of tobacco plant

Caffeine

N

N N

NCH3

O

O CH3

CH3

Caffeine, coffee beans and tea

Procaine

NH2N

CH3CH2

CH3CH2

CH2CH2 O C

O

Procaine (novocaine), painkiller

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

Aromatic Amides

C

O

NH2

Benzamide

C

O

NHCH3

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

ClassificationMonosaccharides

Structures of Important MonosaccharidesCyclic 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.

aldose, hexose ketose, pentose

C

C

CH2OH

H OHC

OHH C

OHH

H OH

C OH

C

C

CH2OH

OHH C

HHO

O

CH2OH

Glucose

C

C

CH2OH

H OHC

OHH C

HHO

H OH

C OH

D-Glucose

Fructose

C

C

CH2OH

H OHC

OHH C

HHO

O

CH2OH

D-Fructose

Galactose

D-galactose

C

C

C

C

C

CH2OH

OH

OHH

HO H

HHO

OHH

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

oCH2OH

OHOH

OH

OH

oCH2OH

OHOH

OH

OH

-D-Glucose -D-Glucose

STOP! Learning Check #11

1. What is a carbohydrate?

2. Name 3 common Monosaccharides and draw their chemical structures.

Carbohydrates

DisaccharidesPolysaccharides

Important Disaccharides

• Maltose = Glucose + Glucose

• Lactose = Glucose + Galactose

• Sucrose = Glucose + Fructose

Maltose

-1,4-glycosidic bond

- D-Maltose

OH

OH

OH

CH2OH

O

O

OH

OH

OH

CH2OH

O

Lactose

-1,4-glycosidic bond

α-D-Lactose

HO

OH

OH

CH2OH

OO

OH

OH

OH

CH2OH

O

Sucrose

O

CH2OH

OH

OH

CH2OH

oCH2OH

OHOH

OH

O

α, -1,2-

glycosidic bond

C12 H22 O11

Table Sugar!

Polysaccharides

• Starch

Amylose

Amylopectin

• Glycogen

• Cellulose

Polysaccharides• Polymers of D-Glucose

OH

OH

OH

OH

CH2OH

O

Amylose

Polymer with α-1,4 bonds

α-1,4 bonds

OOH

OH

CH2OH

O

O

OH

OH

CH2OH

O

O

OH

OH

CH2OH

O

O O

OH

OH

CH2OH

O

Amylopectin

Polymer with α-1,4 and α-1,6 bonds branches

α-1,6 bond

α-1,4 bonds

OOH

OH

CH2OH

O

O

OH

OH

CH2OH

O

O

OH

OH

CH2

O

O O

OH

OH

CH2OH

O

OOH

OH

CH2OH

O

O

OH

OH

CH2OH

O

O

OH

OH

CH2OH

O

O

Cellulose

Polymer with ß-1,4 bonds

ß-1,4 bondsO

O

OH

OH

CH2OH

O

O

OH

OH

CH2OH

O

O

OH

OH

CH2OH

O

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.

STOP! Learning Check #12

LipidsTypes 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

COOH

palmitoleic acid, an unsaturated fatty acid

palmitic acid, a saturated acid

Structures

Saturated fatty acids• Fit closely in regular pattern

Unsaturated fatty acids• Cis double bonds

COOHCOOHCOOH

C CH H

COOHcis double bond

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 UnsaturatedFatty 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

HO

CH3

CH3 CH3

CH3

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

CH3

HO

CH3

CH3OH C

O

N

H

CH2COO- Na+

OH

gycine, an amino acid

cholic acid, a bile acid

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

O

CH3

CH3OH

HO

CH3

CH3OH

testosterone estradiol

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?