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Enrichment Assignment Western School of Health and Business Careers Introduction to Chemistry * Basic Concepts of Organic Chemistry * Common Organic Molecules * Medicinal Chemistry and the Click on me .. and I’ll sing to you! 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 HCH 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 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 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 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 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 CH2OH 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?