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Name __________________________ Mrs. Murray Date ____________ Chemistry UNIT 13: Organic Chemistry Text : Chapter 21: Hydrocarbons, pages 744-765 Chapter 22: Substituted Hydrocarbons and Their Reactions, pages 786-812 A. Organic Chemistry Review Organic chemistry is the study of carbon compounds…let’s see what you remember about carbon… 1. What is the electron configuration of carbon? ______________________ 2. How many valence electrons does carbon have? _________________ 3. Draw Lewis Dot structure for carbon 4. What type of bond will carbon form with hydrogen in CH4? (ionic or covalent)____________ 5. Draw the Lewis Dot structure for CH4 6. What shape is CH4? ___________________ 7. Is this a polar or non-polar molecule? ____________________ Why?___________________________________________________________________ 8. What forces of attraction are present in CH4?___________________________________ 9. Are these weak or strong forces? ___________________________________________ 10. Is CH4 melting /boiling point high or low? ________________________________ 11. Will CH4 dissolve in water? _____________________________________ Explain. _________________________________________________________ B. Naming Alkanes: 1. 2. 3. 4. 5. 6. 7. Draw structural formulas for the following molecules: 8. 2,2,3-trimethyl-butane 9. 3-ethyl-2,2-dimethyl-hexane 10. 2,3,4,5,6,7-hexamethyl-octane C. More Naming Alkanes 1. 2. 3. 5. 4. 6. 7. Draw structural formulas for the following molecules: 8. 4-ethyl-octane 9. 2-methyl-nonane 10. 2-methyl-2-ethyl-butane D. Naming Hydrocarbons: Alkanes, Alkenes and Alkynes 1. 2. 3. 5. 7. Draw the structures for the following compounds: 8. 2,3 dimethyl pentane 9. 2 - butene 10. 3,3 dimethyl 1-hexene 11. 3 ethyl 1-pentyne 4. 6. E. Substituted Hydrocarbons: Circle the functional group in each molecule. Based on the functional group, classify and name each organic compound. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. Draw the following: 11. 3 pentanone 12. pentanoic acid 13. ethyl propanoate F. Substituted Organic Compounds COMPOUND 2- butanol 3- heptanone ethyl butanoate pentanal diethyl ether Class Structure and Structural Formula Isomer Class Isomer Structure and Structural Formula Isomer Name butanoic acid 2-pentanone 1-hexanol methyl propyl ether methyl ethanoate G. Reactions For the following reactions, write the balanced equations for the complete combustion of the following: 1. propane, C3H8 (gas used in torches and gas grills) 2. methanol, CH3OH (race car fuel) Identify the reaction type. Predict the products. + Br2 3. CH4 4. C3H6 + Cl2 5. methanol and propanoic acid 6. ethanol + butanoic acid H. Document Based Question Denatured Alcohol Products such as mouthwash, after-shave, hair spray, and perfume all contain ethanol. However, the ethanol used in these products is not pure. It is treated with chemicals that make it unsuitable for human consumption. Treated ethanol is called denatured alcohol. Ethanol is an excellent solvent for organic and inorganic compounds. It can be added to gasoline to make gasohol. Ethanol can be used to make organic compounds such as diethyl ether. Ethanol is also the alcohol in alcoholic beverages. The government places an excise tax on ethanol used in alcoholic beverages. About 25% to 60% of the price of a bottle of distilled spirits goes to the federal government. In order for ethanol not to be taxed, it must be denatured. This has to be done without making the ethanol product useless. The products used to denature the ethanol must also be difficult to remove by physical or chemical separation. There are about 60 different formulas allowed by the Bureau of Alcohol, Tobacco, and Firearms. These formulas are noted on the bottle. For example, a label might be "S.D.A. Alcohol 40 (14%)." This label means specially denatured alcohol, government formula number 40, and 14% alcohol by volume. Mouthwashes may contain ethanol as a solvent. The problem with denaturing the alcohol in this product is that it cannot be toxic or so bitter that people do not use it. Questions: 1. What is the formula and structural formula of ethanol? What organic class does it belong to? 2. Ethanol can be used to make diethyl ether. Draw the compound di-ethyl ether, along with its structural formula. 3. Draw and name an isomer of di-ethyl ether. 4. What does denaturing do to ethanol? I. Regents Questions Base your answers to questions 1-2 on the information below. Given the reaction between 1-butene and chlorine gas: C4H8 + Cl2 → C4H8Cl2 1. Which type of chemical reaction is represented by this equation? 2. In the space draw the structural formula of the product 1,2-dichlorobutane. Base your answers to questions 3-6 on the information and diagram below and on your knowledge of chemistry. Crude oil is a mixture of many hydrocarbons that have different numbers of carbon atoms. The use of a fractionating tower allows the separation of this mixture based on the boiling points of the hydrocarbons. To begin the separation process, the crude oil is heated to about 400°C in a furnace, causing many of the hydrocarbons of the crude oil to vaporize. The vaporized mixture is pumped into a fractionating tower that is usually more than 30 meters tall. The temperature of the tower is highest at the bottom. As vaporized samples of hydrocarbons travel up the tower, they cool and condense. The liquid hydrocarbons are collected on trays and removed from the tower. The diagram below illustrates the fractional distillation of the crude oil and the temperature ranges in which the different hydrocarbons condense. 3. State the trend between the boiling point of the hydrocarbons contained in the crude oil and the number of carbon atoms in these molecules. 4. Describe the relationship between the strength of the intermolecular forces and the number of carbon atoms in the different hydrocarbon molecules. 5. Write an IUPAC name of one saturated hydrocarbon that leaves the fractionating tower at less than 40°C. 6. How many hydrogen atoms are present in one molecule of octane? Base your answers to questions 7and 8 on the condensed structural formula below. CH3CH2CHCH2 7 In the space provided in your answer booklet, draw the structural formula for this compound. 8. The formula below represents a product formed when HCl reacts with CH3CH2CHCH2. What is an IUPAC name for this product? 9. Given the equation: To which class of organic compounds does product X belong? 10. Identify the homologous series of hydrocarbons to which CH3CH2CH3 belongs. UNIT 13: Organic Chemistry 1. Organic Chemistry is the study of carbon compounds. 2. Using REFERENCE TABLE P, know how to name all straight chain and branched hydrocarbons. 3. Isomers are organic compounds with the same formula, but different structures. 4. C-C bonds can be saturated (single) or unsaturated (double or triple). 5. Hydrocarbons - contain only carbon and hydrogen. There are four types (TABLE Q) Alkanes Alkenes Alkynes Benzene all single bonds double bond triple bond 1 1/2 bond saturated unsaturated unsaturated saturated CnH2n+2 CnH2n CnH2n-2 CnH2n-6 ethane ethene ethyne (acetylene) benzene/ toluene -ANE suffix -ENE suffix -YNE suffix 6. Substituted hydrocarbons: Review organic REFERENCE TABLE R. Know how to draw name and functional group of each substituted hydrocarbon. 7. ISOMERS of substituted hydrocarbons go in order pairs on TABLE R. 8. Alcohols may be monohydroxy (1-OH), dihydroxy (2-OH) or trihydroxy (3-OH). 9. Alcohols may be primary, secondary or tertiary. 10. Alkanes can undergo substitution reactions (SUBSTITUTING 1 halogen for a hydrogen ). 11. Alkenes can undergo addition reactions ( ADDING DIATOMIC for the double bond). 12. Nylon, protein, & starch are polymers. 13. Condensation polymerization reaction (dehydration synthesis) produces water and a polymer from monomers. 14. Alcohol and an organic acid react to produce an ester and water. 15. Fermentation is a process which converts sugar to alcohol in the presence of a catalyst (yeast).