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 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 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 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.

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.

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.

IUPAC NAMES Hexane 6 CH3CH2CH2CH2CH2CH3 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 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 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

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

Alkanes and Aromatic Hydrocarbons Cycloalkanes Aromatic Hydrocarbons

Each corner or point on a ring represents a carbon atom! Cycloalkanes Cyclopropane CH2 CH2 CH2 Cyclobutane CH2 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!

More Cycloalkanes Cyclopentane CH2 CH2 CH2 CH2 CH2 Cyclohexane 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.

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.

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.

Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes 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 Ketone

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 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 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 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.

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

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

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

Phenols in Medicine

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?

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 1-propanethiol Garlic CH2= CHCH2-SH 2-propene-1-thiol Skunk 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 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

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

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 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.

Alcohols, Phenols, Ethers, Aldehydes, and Ketones

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

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)

Aldehydes as Flavorings

Glucose is an aldehyde

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

Fructose is a Ketone

Ketones as Hormones

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

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.

Carboxylic Acids, Esters, Amines and Amides Properties of Carboxylic Acids Esters Esterification and Hydrolysis Getting closer to the end! Click on the lemons for a pep-me-up song! 

Carboxyl Group Carboxylic 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 What is a carboxyl group? What is the formula for the carboxylic acid: acetic acid? What is a pleasant quality of esters?

Carboxylic Acids Esters, Amines and Amides 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

Caffeine

Procaine

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

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.

Structures of Important Monosaccharides 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.

aldose, hexose ketose, pentose

Glucose

Fructose

Galactose 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

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

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

Carbohydrates Disaccharides Polysaccharides

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

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

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

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

Polysaccharides Starch Amylose Amylopectin Glycogen Cellulose

Polysaccharides Polymers of D-Glucose

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

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

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

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.

Chemical Properties of Triglycerides 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

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

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 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.

Steroids Steroid nucleus 3 cyclohexane rings 1 cyclopentane ring

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

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

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

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?