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Iowa State University *

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Chemistry

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Feb 20, 2024

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NEW TEMPLATE: INTRO TO ORGANIC CHEMISTRY LAB Pre-lab Questions Procedure and Safety 1. (10 pts) Write a bulletpoint list outline of the procedure. This is an example from a different experiment. Note that you don’t need EVERY detail. Distillation Procedure Summary Set up chilled water supply and attach to condenser Turn on chilled water and check condenser for leaks Add 15 mL of binary mixture and stirbar to 25 mL rbf Set up distillation apparatus and have TA check Insulate rbf and column with glass wool Have two more flasks ready for collecting fractions Turn regulator on and heat so gently boiling (don't forget to stir) Collect the first fraction as long as the temp remains constant (record temp) Change to second receiving flask when temp changes Increase heat Change to third receiving flask when temp is constant again (record temp) STOP WHEN 2-3 mL left in rbf! Turn heat off Take IR of 1 st and 3 rd fraction Put waste in waste container, clean up, plug in iPad and put crayon in holder Write your procedure bullet point list here: 2. (4 pts) Write a brief summary of the key safety concerns specific for this experiment. (Hint: look at the Safety for this Experment section in the Safety and Procedure document that you download from the experiment page on Canvas. Remember not to cut and paste.) Part 1: Solubility 3. (40 pts total, 5 pts ea) In the provided space in the lab report template, draw the bond-line structure of each of the solid compounds and solvents you will use today. Watch How to Draw Bond Line Structures before attempting this question. Bondline Structures and Polarity Name Lewis Structure Bond-line Structure Polar (P) or Nonpolar (N) Solids benzoic Acid
2 N naphthalene N 2-naphthol p Solvents (liquids) hexane N dichloromethane n ethyl acetate
3 n ethanol p 4. (28 pts, 2 pts ea label, 2 pts ea circle) Examine the structure of each and decide whether each solid is polar or nonpolar. Indicate in the provided column in the table above. Do the same for solvents. Circle the atoms in each polar solid or solvent which cause the compound to be polar. Watch Ionic, Polar Covalent and Non-Polar Covalent Bonding in Organic Chemistry before attempting this question. At 4:17, Leah begins explaining how to tell if a covalent compound is polar or nonpolar. 5. (24 pts, 2 pts ea) Based on the information you provided in the above questions and the guideline you learned from general chemistry which states “Like dissolves like” (i.e polar solvents dissolve polar compounds and nonpolar solvents dissolve nonpolar compunds), predict which solids will dissolve in which solvents. Fill in the following table with your predictions. Solubility Predictions Fill in S for soluble and I for insoluble Hexane Dichloromethane Ethyl acetate Ethanol Benzoic acid s s s i Naphthalene s s s i 2-Naphthol i i i s Part 2: Melting Points 6. (24 pts, 2 pts ea IMF, 2 pts each ranking) For each solid compound, determine what kind of intermolecular forces are happening between molecules of each compound based on the structure of the compound. Add these to the table below. Based on the types of intermolecular forces, predict which solid has the highest, middle, and lowest melting points and fill in the table. Melting Point Predictions Type of IMF(s) Melting Point Ranking Benzoic acid Heat energy? Highest Naphthalene Heat energy? Middle 2-Naphthol Heat energy? lowest
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4 Data and Observations Part 1 (60 pts, 5 pts ea) Solubility Observations Fill in S for soluble, I for insoluble, and SS for slightly soluble Hexane Dichloromethane Ethyl acetate Ethanol Benzoic acid i s s s Naphthalene 0.187g SS S S I 2-Naphthol Part 2 (15 pts, 5 pts ea) Melting Point Observations Melting Point ( o C) Benzoic acid 114 Naphthalene 95 2-Naphthol Analysis and Application Questions Analysis 1. In order to answer this question, compare your predicted solubility from pre-lab questions with the class observations for solubility for Part 1 of the experiment. a. (20 pts) Based on your incorrect predictions, did any of the solids or solvents behave differently than you expected? If so, list the solvent and solid as well as the unexpected result. No I predicted correctly. b. (20 pts) If you had an unexpected result, it is probably due to polarizabilty. (Watch this short video for a brief animation about polarizability.) Given that a larger molecule is often more polarizable that a smaller molecule with similar polarity , explain briefly why naphthalene dissolves more easily in ethyl acetate than dichloromethane. Napthalene is a larger molecule therefore it dissolves easier. 2. Compare your predicted ranking of melting points for the solids from the pre-lab question with the observed melting points. a. (20 pts) Based on the structure and types of intermolecular forces, one might predict that benzoic acid has a significantly higher melting point than 2-naphthol, but it does not. What is different about the structures of benzoic acid and 2-naphthol that could explain the similar melting points? 2-Napthol is a polar molecule and those require more heat energy to change. Application 3. (20 pts) Petrolatum is an organic compound composed of a mixture of alkanes (organic compounds only containing carbons, hydrogens, and single bonds) obtained from petroleum. It is often added to skin care products since it softens near body temperature forms a protective barrier that prevents moisture loss. If a new skin care product does not soften on application as expected, what suggestion would you give to decrease the melting point of the product based on petrolatum composition? In other words, how
5 might you change the size of the alkane molecules used in the petrolatum to make it melt at a lower temperature? Make the mixture of alkanes less polar. 4. (15 pts, 5 pts solvent choice, 10 pts explanation) Polystyrene is a plastic composed of repeating units of styrene. Its structure is shown below. Polystyrene is one of the major products of the petrochemical industry. In order to synthesize polystyrene from styrene, a solvent that dissolves styrene is needed. Based on your observations during this experiment, suggest a solvent. Remember to consider polarizability AND like dissolves like. Briefly explain your choice. Stryrene is a polar molecule so to dissolve it, we would need a polar solvent, such as ethenol. However, Styrene is more polarizable than ethenol because it is a smaller molecule.