MOLECULAR NATURE OF MATTER 7/E LL W/AC
7th Edition
ISBN: 9781119664796
Author: JESPERSEN
Publisher: WILEY
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Chapter 12, Problem 85RQ
What are the molecular mass and molecular formula of a nondissociating molecular compound whose empirical formula is
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Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
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other impurities are present in your product and how do you know?
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1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
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Synthesis of ZybanⓇ:
1. Write a mechanism for the bromination of m-chloropropiophenone.
Br₂
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Cl
Br
2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks).
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Chapter 12 Solutions
MOLECULAR NATURE OF MATTER 7/E LL W/AC
Ch. 12 - Which substances will be soluble in water? (a)...Ch. 12 - Which substances will be soluble in nonpolar...Ch. 12 - Draw an enthalpy diagram for the endothermic...Ch. 12 - When potassium hydroxide is dissolved in water,...Ch. 12 - Prob. 5PECh. 12 - When sodium hydroxide is dissolved in water, the...Ch. 12 - At 25C and standard pressure, a hydrogen sulfide...Ch. 12 - How many grams of nitrogen and oxygen are...Ch. 12 - What volume of water at 20.0C(d=0.9982gmL-1) is...Ch. 12 - Prob. 10PE
Ch. 12 - Prob. 11PECh. 12 - Water freezes at a lower temperature when it...Ch. 12 - Prob. 13PECh. 12 - Prob. 14PECh. 12 - Prob. 15PECh. 12 - Prob. 16PECh. 12 - Dibutyl phthalate, C16H22O4 (molar mass...Ch. 12 - Prob. 18PECh. 12 - At , the vapor pressure of cyclohexane, a nonpolar...Ch. 12 - Using the information from Practice Exercise...Ch. 12 - In making candy, a certain recipe calls for...Ch. 12 - How many grams of glucose (molar mass = 180.9 g...Ch. 12 - A solution made by dissolving 3.46 g of an unknown...Ch. 12 - Prob. 24PECh. 12 - What is the osmotic pressure, in mm Hg and mm H2O,...Ch. 12 - What is the osmotic pressure in torr of a 0.0115 M...Ch. 12 - Estimate the molecular mass of a protein when...Ch. 12 - Prob. 28PECh. 12 - Calculate the freezing point of aqueous 0.237mLiCl...Ch. 12 - Determine the freezing point of aqueous solutions...Ch. 12 - Prob. 31PECh. 12 - Prob. 32PECh. 12 - Intermolecular Forces and the Formation of...Ch. 12 - Intermolecular Forces and the Formation of...Ch. 12 - Intermolecular Forces and the Formation of...Ch. 12 - Intermolecular Forces and the Formation of...Ch. 12 - Intermolecular Forces and the Formation of...Ch. 12 - Intermolecular Forces and the Formation of...Ch. 12 - Prob. 7RQCh. 12 - Intermolecular Forces and the Formation of...Ch. 12 - Heats of Solution
12.9 The value of for a soluble...Ch. 12 - Heats of Solution Referring to Question 12.9,...Ch. 12 - Heats of Solution Which would be expected to have...Ch. 12 - Heats of Solution
12.12. Suggest a reason why the...Ch. 12 - Prob. 13RQCh. 12 - Prob. 14RQCh. 12 - Heat of solution When a certain solid dissolves in...Ch. 12 - Heat of solution
12.16 If the value of for the...Ch. 12 - Prob. 17RQCh. 12 - Solubility as a Function of Temperature
12.18 If a...Ch. 12 - Solubility as a Function of Temperature Anglers...Ch. 12 - Henry's Law
12.20 What is Henry’s law?
Ch. 12 - Henry's Law
12.21 Mountain streams often contain...Ch. 12 - Henry's Law Why is ammonia so much more soluble in...Ch. 12 - Prob. 23RQCh. 12 - Prob. 24RQCh. 12 - Prob. 25RQCh. 12 - Prob. 26RQCh. 12 - Concentration Units Suppose a 1.0 m solution of a...Ch. 12 - Colligative Properties What specific fact about a...Ch. 12 - Colligative Properties
12.29. What is Raoult’s...Ch. 12 - Colligative Properties Why does a nonvolatile...Ch. 12 - Prob. 31RQCh. 12 - Prob. 32RQCh. 12 - Prob. 33RQCh. 12 - Prob. 34RQCh. 12 - Prob. 35RQCh. 12 - Prob. 36RQCh. 12 - Prob. 37RQCh. 12 - Prob. 38RQCh. 12 - Colligative Properties
12.39 When a solid is...Ch. 12 - Colligative Properties
12.40 What is the...Ch. 12 - Prob. 41RQCh. 12 - Colligative Properties What is the vant Hoff...Ch. 12 - Prob. 43RQCh. 12 - Prob. 44RQCh. 12 - Prob. 45RQCh. 12 - Prob. 46RQCh. 12 - Heterogeneous Mixtures What is the Tyndall effect?Ch. 12 - Heterogeneous Mixtures
12.48 What is a micelle,...Ch. 12 - Heat of Solution For an ionic compound dissolving...Ch. 12 - Heat of solution
12.50 Consider the formation of a...Ch. 12 - Henry's Law The solubility of methane, the chief...Ch. 12 - Henry's Law If the solubility of a gas in water is...Ch. 12 - At 740 torr and 20.0C, nitrogen has a solubility...Ch. 12 - Hydrogen gas has a solubility in water of...Ch. 12 - 12.55. If 100.0 mL of water is shaken with oxygen...Ch. 12 - 12.56 Helium gas can be used to displace other...Ch. 12 - Concentration Units Muriatic acid is the...Ch. 12 - Prob. 58RQCh. 12 - What mass of a 0.853 molal solution of iron(III)...Ch. 12 - In order to conduct three experiments that...Ch. 12 - Prob. 61RQCh. 12 - A solution of acetic acid, CH3COOH, has a...Ch. 12 - Prob. 63RQCh. 12 - Botulinum toxin is one of the most acutely toxic...Ch. 12 - A solution of fructose, C6H12O6, a sugar found in...Ch. 12 - Prob. 66RQCh. 12 - Prob. 67RQCh. 12 - Prob. 68RQCh. 12 - Prob. 69RQCh. 12 - An aqueous solution of isopropyl alcohol, C3H8O,...Ch. 12 - Sodium nitrate, NaNO3, is sometimes added to...Ch. 12 - In an aqueous solution of sulfuric acid, the...Ch. 12 - Colligative Properties At 25C, the vapor pressure...Ch. 12 - Colligative Properties The vapor pressure of water...Ch. 12 - 12.75 At the vapor pressures of benzene and...Ch. 12 - Pentane (C5HI2)andheptane(C7HI6) are two...Ch. 12 - *12.77 Benzene and toluene help achieve good...Ch. 12 - The vapor pressure of pure methanol, CH3OH, at 33C...Ch. 12 - A solution containing 8.3 g of a nonvolatile,...Ch. 12 - At 21.0C, a solution of 18.26 g of a nonvolatile,...Ch. 12 - 12.81 How many grams of sucrose are needed to...Ch. 12 - Prob. 82RQCh. 12 - A solution of 12.00 g of an unknown...Ch. 12 - 12.84 A solution of 14 g of a nonvolatile,...Ch. 12 - What are the molecular mass and molecular formula...Ch. 12 - Benzene reacts with hot concentrated nitric acid...Ch. 12 - 12.87 (a) Show that the following equation is...Ch. 12 - A saturated solution is made by dissolving 0.400 g...Ch. 12 - Prob. 89RQCh. 12 - How many grams of A1C13 would have to be dissolved...Ch. 12 - 12.91 What is the osmotic pressure, in torr, of a ...Ch. 12 - Below are the concentrations of the most abundant...Ch. 12 - 12.93 What is the expected freezing point of a...Ch. 12 - Prob. 94RQCh. 12 - 12.95 The van’t Hoff factor for the solute in is...Ch. 12 - 12.96 What is the expected van’t Hoff factor for ...Ch. 12 - Prob. 97RQCh. 12 - *12.98 The “bends” is a medical emergency caused...Ch. 12 - In order for mosquitos to survive the cold winter,...Ch. 12 - The vapor pressure of a mixture of 0.400 kg of...Ch. 12 - Ethylene glycol, C2H6O2, is used in many...Ch. 12 - What is the osmotic pressure in torr of a 0.010 M...Ch. 12 - The osmotic pressure of a dilute solution of a...Ch. 12 - Prob. 104RQCh. 12 - Consider an aqueous 1.00 m solution of Na3PO4,a...Ch. 12 - A 2.50 g sample of aluminum chloride and sodium...Ch. 12 - Prob. 107RQCh. 12 - A sample containing only iron(II) nitrate and...Ch. 12 - Prob. 109RQCh. 12 - Prob. 110RQCh. 12 - How many mL of 0.223MK2Cr2O7 are needed to...Ch. 12 - Prob. 112RQCh. 12 - A certain organic substance is soluble in solvent...Ch. 12 - Prob. 114RQCh. 12 - Prob. 115RQCh. 12 - Having had some laboratory experience by now,...Ch. 12 - 12.117 This chapter focused on the physical...Ch. 12 - 12.118 Using the principles developed in this...Ch. 12 - Prob. 119RQCh. 12 - Prob. 120RQCh. 12 - Prob. 121RQCh. 12 - Consider a solution that has the maximum amount of...Ch. 12 - 12.123 When a 10.0 molar solution of sodium...
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- Synthesis of Ibuprofen-Part 2: 1. Some pain relievers including ibuprofen (MotrinⓇ) and naproxen (Aleve®) are "α-arylpropanoic acids." Look up the structure of naproxen (AleveⓇ), another a-arylpropionic acid. Using the same reactions that we used for making ibuprofen, show how to make naproxen from the compound below. Show all intermediates and reagents in your synthesis. Show how you would prepare ibuprofen starting from p-isobutylbenzene rather than p-isobutylacetophenenone. What reaction steps would need to change/add? 3. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAcid Catalyzed Aromatization of Carvone: 1. Starting with the ketone, below, draw a mechanism for the reaction to give the phenol as shown. H2SO4 HO- H₂O 2. Why do we use CDCl instead of CHCl, for acquiring our NMR spectra? 3. Why does it not matter which enantiomer of carvone is used for this reaction? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAssign this H NMRarrow_forward
- Please complete these blanks need that asaparrow_forwardNitration of Methyl Benzoate: 1. Predict the major product for the reaction below AND provide a mechanism. Include ALL resonance structures for the intermediate. C(CH3)3 NO₂* ? 2. Assuming the stoichiometry is 1:1 for the reaction above, what volume of concentrated nitric acid would be required to mononitrate 0.50 grams of the compound above? What product(s) might you expect if you nitrated phenol instead of methyl benzoate? Explain your reasoning. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSodium Borohydride Reduction (continued on the next page): 1. Draw the product of each of the reactions below and give the formula mass to the nearest whole number. ? (1) NaBH (2) acid (1) NaBD4 (2) acid ? 2. In mass spectra, alcohols typically break as shown in equation 8 in chapter 11 (refer to your lab manual). The larger group is generally lost and this gives rise to the base peak in the mass spectrum. For the products of each of the reactions in question # 1, draw the ion corresponding to the base peak for that product and give its mass to charge ratio (m/z). 3. Given the reaction below, calculate how many mg of 1-phenyl-1-butanol that can be produced using 31 mg NaBH4 and an excess of butyrophenone. 4. + NaBH4 OH (after workup with dilute HCI) What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forward
- Aspirin from Wintergreen: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? Write a step-by-step mechanism for the esterification of salicylic acid with acetic anhydride catalyzed by concentrated H₂SO4. 3. Calculate the exact monoisotopic mass of aspirin showing your work. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardSynthesis of Ibuprofen-Part 1: 1. What characteristic absorption band changes would you expect in the IR spectrum on going from p-isobutylacetophenone to 1-(4-isobutylphenyl)-ethanol and then to 1-(4-isobutylphenyl)-1-choroethane as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. Given that the mechanism of the chlorination reaction today involves formation of a benzylic carbocation, explain why the following rearranged product is not formed. محرم محمد 3. Why do we use dilute HCl for the first step of the reaction today and concentrated HCI for the second step? What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?arrow_forwardAssign only the C NMRarrow_forward
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Solutions: Crash Course Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=9h2f1Bjr0p4;License: Standard YouTube License, CC-BY