Chemistry Problems Spring Semester
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1 Early Booklet E.C.: / 2 Total HW Points Unit 5: / 28 Total Lab Points Unit 5: / 18 Late Fees? Y/N Chemistry Problems Spring Semester Unit 5 Hydrocarbons & Organic Chemistry Chapters of your book. 5.1 Problems Alkanes Section of your textbook. 1. Rank the compounds listed in the following table in order in which they will be distilled out of a mixture. Rank them in order of first to distill to last to distill. Compound Boiling Point o C hexane 68.7 methane octane butane -0.5 propane Draw the structural formulas and line structures of each of the following: 2. Ethane Hexane 5.1 HW Points: / 8 Late/Inc. Fee: Propane Heptane Name the compound represented by each of the following structural formulas: 4. CH 3 CH 2 CH 2 CH 2 CH Draw line structures for the following compounds: 7. heptane 2-methylhexane 8. 2,3-dimethylpentane 2,2-dimethylpropane 9
2 5.2 Problems Alkenes and -ynes Section 21.3 of your textbook. 5.2 HW Points: / 7 Late/Inc. Fee: Explain how alkanes, alkenes, and alkynes; differ from each other. Name the compound represented by the line structures Draw line structures for the following: 4. 2, 4-dimethyl-1-octene 5. 2,2-dimethyl-3-hexyne 6. How are two isomers alike, and how are they different? 7. Define Polymer. 10
3 5.3 Problems Aromatics Section 21.5 of your textbook. 5.3 HW Points: / 6 Late/Inc. Fee: - 2 Name the compound represented by each of the condensed structural formulas What structural characteristic do all aromatic hydrocarbons share? 4. Draw the line structure of 1,2-dimethylbenzene. Name the compound represented by each of the following structural formulas
4 5.4 Problems Functional Groups Section of your textbook. 5.4 HW Points: / 7 Late/Inc. Fee: What is a functional group? 2. What reactant would you use to convert methane to bromomethane? Circle and name each of the functional groups in the structures below Draw structural formulas for the following molecules. 5. A. 1,2-butanediol B. 2-hexylamine 6. A. 2-methyl-1-butanol B. cyclopentanol 7. Name each of the following carbonyl compounds. a. b. c. 12
5 Chemistry Name: Points: E.C. Missed: Overdue Fee: Unit 5: Take the Benzene Challenge! First Score: Corrections: Clear your desks completely! Correction Credit: Half Final Score: Back in 1975, marketers for Pepsi launched a campaign called the Pepsi Challenge, in which a blindfolded taster tried samples of Coke and Pepsi. The taster then selected which one he or she preferred. There was a significant proportion of the population that preferred Pepsi, so based on this, the Pepsi Corporation claimed a victory over its arch nemesis. Now, 38 years later, it s time for you to take a similar challenge the Benzene Challenge! You won t get to drink this poisonous, carcinogenic, and flammable hydrocarbon, however. Materials List: 6 Carbon Atoms 6 Hydrogen Atoms 9 Short Single Bonds 6 Long Multiple Bonds Your Mission You must build a benzene molecule, with the materials provided. No books, computers or anything else is permitted just your great brains. Remember, each carbon needs to have four bonds. Each hydrogen atom can have only one bond. One hint about this molecule, it is very symmetric. Scoring: 6 points Figure out the structure of benzene within 10 minutes, and draw it here. E. C. 1 Point Be the first group to determine the structure! Good Luck! 13
6 Chemistry Name: Points: Missed: Overdue Fee: 12-4 Unit 5: Steam Distillation Lab First Score: Corrections: Correction Credit: Half Final Score: Overview: In the early days of organic chemistry research, scientists distilled many different compounds to see what was in them. They discovered that many natural materials produced oily compounds when distilled. These were dubbed Essential Oils, because they seemed to contain the essence of the materials. In this lab, you and your group will extract essential oils from cloves using a technique called steam distillation. Steam distillation is a method to isolate essential oils by using the steam produced by boiling water as a carrier for the less volatile molecules to be distilled. The primary essential oil in cloves is called eugenol, and has a benzene ring with various side chains. With any luck you will be able to see the clove oil at the end of the lab. Materials: 10 Whole Cloves Mortar and Pestle Distillation Apparatus - Ring Stand with Wire Mesh - Evaporation Unit (500 ml Erlenmeyer Flask) - Transporting Unit (Rubber Stopper With Tubing) - Condensing Unit (glass bottle with hole drilled in it) - Collector (Large Test Tube) Procedure: 1. Set up the distillation apparatus as demonstrated at Lab Station 1 Be sure collection tube is well positioned 2. Pour 100 ml tap water into the Erlenmeyer flask. 3. Count out 10 cloves and grind them in the mortar and pestle. 4. Pour the ground cloves into the flask, then put the rubber stopper and tubing on. 5. Bring the water to a gentle boil, making sure that it doesn t boil too rapidly (that causes chunks of cloves to be pushed into the tubing). Adjust flame height accordingly. 6. Boil for about 5-10 minutes, or until the test tube has 2 cm water and oil. 7. After the boiling is done, shut off your gas. 8. Look at the top of the collection tube hopefully there is a thin layer of oily residue there that s the clove oil! Cleanup: After 10 minutes of cooling, pour the clove/water mixture from your Erlenmeyer flask down the drain and rinse the flask: careful HOT!!! Pour your water and clove oil down the drain and rinse. Leave the distillation apparatus for the next class. 14
7 Questions: 3 Points per Molecule. The following molecules are different essential oils of different plants. 1. Circle and label all the functional groups. 2. Label the benzene rings, and put a box around each non-benzene double bond. 3. Write the chemical formula for each molecule (Example: C x H y O z ) Eugenol Clove Oil Formula = Cinnamaledhylde Cinnamon Oil Formula = Anise Oil (licorice flavor) Formula = Cardamom Oil Formula = 15
8 Chemistry Name: Unit 5: Naming Alkanes Worksheet Points: E.C Missed: Late Fee: (Overdue) First Score: Corrections: Correction Credit: Full Final Score: We will correct this two-page worksheet tomorrow in class, but finish it before you leave today. You can get full credit on corrections you make, so don t be shy about trying problems that look difficult. Use your IUPAC rules to name the following alkanes (1 point each):
9 Use your IUPAC rules to draw the following alkanes (1 point each): 6. Hexane 7. 3-ethylheptane 8. 3-isopropyl-2-methyloctane 9. 3,6-diethyldecane ethyl-2,3,5-trimethylnonane Extra Credit (1 Point): Name the following molecule: 17
10 Chemistry Name: Points: E.C. Missed: Late/ Incomplete Fee: First Score: Corrections: Unit 5: Naming Aromatics Worksheet Correction Credit: Full Final Score: We will correct this in class tomorrow finish it before you leave. Name the cyclic compounds (1 point each): Name the branched cyclic/aromatic compounds (1 point each):
11 (1 Point) What structural characteristic do all aromatic hydrocarbons share? Draw the structural formula of (1 point each): 12. 1,3-dimethylbenzene ,4-diethyl-2-methylbenzene butyl-2,4-dimethylcyclooctane E.C. (1 Point) Draw the structure of: 1-ethyl-2-isopropyl-7-propyl-2,4,5-trimethylcyclononane. 19
12 Chemistry Names: Functional Groups Worksheet Period: Points: E.C. Missed: Late Fee: (Overdue) 8-2 Correction Credit Back: Full Corrections: One per Team Score: Your objective is to complete the following problems within 30 minutes. I will approve of each answer to verify that you re completing the assignment. Materials List: Modeling Kit: 6 Black Carbon Atoms 12 White Hydrogen Atoms 2 Green Halogen Atoms (F, Cl, Br, or I) 2 Red Oxygen Atoms 2 Blue Nitrogen Atoms Assorted Short Single Bonds Assorted Long Multiple Bonds Problem 1 Approval. Name the following molecule: Problem 2 Approval. Name the following molecule: Problem 3 Approval. Draw, then model the following molecule: 1-chloro-3-methylbutane Problem 4 Approval. Draw, then model the following molecule: 2-fluoro-1-hexanal 20
13 Problem 5 Approval. Draw the following molecule, then report how many hydrogen atoms it has: 3-bromo-5-ethyl-1-octananol Hydrogen = Problem 6 Approval. Draw then model the following: 2-iodo-3-hexanone Problem 7 Approval. Draw then model the following: 1,3-dichloro-2-methyl-2,3-pentanediol Problem 8 Approval. Name the following: 21
14 Unit 5 Review Problems Chapters of your textbook. Due: Solve these problems and enter your responses in the bubble boxes. Be sure to erase completely, and enter your student ID in the box on the right. Each question is worth one point. If you turn this in late, you will only receive half credit for your work. 1. Choose the structure of 5-butyldecane. 2. Choose the structure of propane. 3. Choose the structure of 4-propyloctane. 4. Choose the structure of 4. 5-ethyl-2,3-dimethylnonane. 5. Name the following molecule using IUPAC rules: A) 4-isopropyl-6-methylheptane B) 2-methyl-4-isopropylheptane 22
15 C) 4-isopropyl-2-methyloctane D) 4-isopropyl-2-methylheptane 6. Name this molecule using IUPAC rules: A) 2-methylbutane B) 2-methylpentane C) hexane D) 2-methylhexane 7. Name the following molecule using IUPAC rules: A) isopropylethane B) butane C) 3-methylbutane D) 2-methylbutane 8. What makes a hydrocarbon saturated. A) having the ability to absorb bromine B) having all single bonds C) having double and single bonds D) having all double bonds 9. Choose the structure of: 3-hexyne 10. Choose the structure of: 3-ethyl-2-methyl-1-pentene 11. Name this molecule using IUPAC rules: A) 6-methyl-2-heptyne B) 2-methyl-5-heptene C) 6-methyl-2-heptene D) 6-methylheptene 12. Choose the structure of: 3-nonanone 23
16 13. Choose the line structure of: dimethyl ether 14. Choose the structure of: 3,5-octanediol 15. Name this molecule using IUPAC rules: A) 4-butanoic acid B) 1-butanoic acid C) 1-butanol D) 1-butanal 16. Name this molecule using IUPAC rules: A) 3-hexylamine B) 3-pentylamine C) 4-hexylamine D) 4-pentylamine 17. Name this molecule using IUPAC rules: A) 2-chloro-3-bromohexane B) 2-chloro-3-bromopentane C) 3-bromo-2-chloropentane D) 3-bromo-2-chlorohexane 18. Name this molecule using IUPAC rules: A) 1-butanoic acid B) 1-butanal C) 1-butanol D) 1-butanone 24
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