MOLECULAR NATURE OF MATTER 7/E LL W/AC
7th Edition
ISBN: 9781119664796
Author: JESPERSEN
Publisher: WILEY
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Chapter 15, Problem 88RQ
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Complete the following table. The only density needed is already given. Show your
calculations in a neat and easy-to-follow manner in the space below the table. All units
should be included and significant figures should be given close attention. Be sure to notice
that the amount of material should be in millimoles rather than moles, and the theoretical
mass of the product should in milligrams rather than grams.
LOCH 3
+
H2SO4
HNO 3
O=C-OCH 3
NO2
x
H₂O
F.W.
4.0 mL 1.3 M
amount
0.50 mL
in H2SO4
mg Theoretical
Theoretical
mmoles
density
1.09
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.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
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?
Wintergreen from Aspirin:
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.
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?
Chapter 15 Solutions
MOLECULAR NATURE OF MATTER 7/E LL W/AC
Ch. 15 - Which of the following are conjugate acid-base...Ch. 15 - Write the formula of the conjugate base for each...Ch. 15 - Sodium cyanide solution, when poured into excess...Ch. 15 - One kind of baking powder contains sodium...Ch. 15 - Which of the following are amphoteric and which...Ch. 15 - The anion of sodium monohydrogen phosphate,...Ch. 15 -
Given that is a stronger acid than what is the...Ch. 15 - Given that HClO is a weaker acid than determine...Ch. 15 - Order the following groups of acids from the...Ch. 15 - Using only the periodic cable, choose the stronger...
Ch. 15 - Prob. 11PECh. 15 - Explain why one acid is weaker than the other in...Ch. 15 - In each pair, explain why one is a stronger acid...Ch. 15 - In each pair, explain why one is a weaker acid...Ch. 15 - How would you expect the acidities of the...Ch. 15 - List these acids in terms of increasing acidity:...Ch. 15 - Identify the Lewis acid and Lewis base in each...Ch. 15 - Is the fluoride ion more likely to behave as a...Ch. 15 - Brnsted-Lowry Acids and Bases How is a...Ch. 15 - Brnsted-Lowry Acids and Bases How are the formulas...Ch. 15 - Brnsted-Lowry Acids and Bases Is H2SO4 the...Ch. 15 - Brnsted-Lowry Acids and Bases What is meant by the...Ch. 15 - Brnsted-Lowry Acids and Bases Define the term...Ch. 15 - Strengths of Bronsted-Lowry Acids and Bases
15.6...Ch. 15 - Strengths of Brønsted-Lowry Acids and Bases
15.7...Ch. 15 - Strengths of Brnsted-Lowry Acids and Bases The...Ch. 15 - Strengths of Brnsted-Lowry Acids and Bases...Ch. 15 - Strengths of Brnsted-Lowry Acids and Bases Acetic...Ch. 15 - Strengths of Brnsted-Lowry Acids and Bases Nitric...Ch. 15 - Strengths of Brnsted-Lowry Acids and Bases HCIO4...Ch. 15 - Strengths of Brnsted-Lowry Acids and Bases Formic...Ch. 15 - Periodic Trends in the Strength of Acids Explain...Ch. 15 - Periodic Trends in the Strength of Acids What are...Ch. 15 - Periodic Trends in the Strength of Acids Within...Ch. 15 - Periodic Trends in the Strength of Acids Explain...Ch. 15 - Periodic Trends in the Strength of Acids Within...Ch. 15 - Periodic Trends in the Strength of Acids Explain...Ch. 15 - Periodic Trends in the Strength of Acids Astatine,...Ch. 15 - Periodic Trends in the Strength of Acids
15.21...Ch. 15 - Periodic Trends in the Strength of Acids
15.22...Ch. 15 - Periodic Trends in the Strength of Acids Which of...Ch. 15 - Periodic Trends in the Strength of Acids Which of...Ch. 15 - Lewis Acids and Bases Define Lewis acid and Lewis...Ch. 15 - Lewis Acids and Bases In terms of atomic orbitals,...Ch. 15 - Lewis Acids and Bases
15.27 Explain why the...Ch. 15 - Lewis Acids and Bases Methylamine has the formula...Ch. 15 - Use Lewis structures to show the Lewis acid-base...Ch. 15 - Lewis Acids and Bases
15.30 Explain why the oxide...Ch. 15 - Lewis Acids and Bases The molecule SbF5 is able to...Ch. 15 - Lewis Acids and Bases In the reaction of calcium...Ch. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Prob. 35RQCh. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Prob. 40RQCh. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Acid-Base Properties of the Elements and Their...Ch. 15 - Prob. 43RQCh. 15 - Advanced Ceramics and Acid-Base Chemistry What is...Ch. 15 - Advanced Ceramics and Acid-Base Chemistry What is...Ch. 15 - Advanced Ceramics and Acid-Base Chemistry
15.46...Ch. 15 - Advanced Ceramics and Acid-Base Chemistry How does...Ch. 15 - Advanced Ceramics and Acid-Base Chemistry
15.48...Ch. 15 - Brønsted-Lowry Acids and Bases
15.49 Write the...Ch. 15 - Brønsted-Lowry Acids and Bases
15.50 Write the...Ch. 15 - Brønsted-Lowry Acids and Bases
15.51 Write the...Ch. 15 - Brnsted-Lowry Acids and Bases Write the formula...Ch. 15 - Brønsted-Lowry Acids and Bases
15.53 Identify the...Ch. 15 - Brønsted-Lowry Acids and Bases
15.54 Identify the...Ch. 15 - Periodic Trends in the Strengths of Acids Choose...Ch. 15 - Periodic Trends in the Strengths of Acids Choose...Ch. 15 - Choose the stronger acid and give your reason:...Ch. 15 - Choose the stronger acid and give your reason:...Ch. 15 - Choose the stronger acid:...Ch. 15 - Choose the stronger acid:...Ch. 15 - Lewis Acids and Bases Use Lewis symbols co diagram...Ch. 15 - Lewis Acids and Bases Use Lewis symbols to diagram...Ch. 15 - *15.63 Beryllium chloride, , exists in the solid...Ch. 15 - Aluminum chloride, AlCl3, forms molecules with...Ch. 15 - Use Lewis structures to diagram the reaction...Ch. 15 - Use Lewis structures to diagram the reaction...Ch. 15 - Use Lewis structures to show how the following...Ch. 15 - *15.68 Use Lewis structures to show how the...Ch. 15 - Acid-Base Properties of Elements and Their...Ch. 15 - Acid-Base Properties of Elements and Their Oxides...Ch. 15 - Prob. 71RQCh. 15 - Prob. 72RQCh. 15 - What is the formula of the conjugate acid of...Ch. 15 - *15.74 Using liquid ammonia as a solvent, sodium...Ch. 15 - In liquid SO2asasolvent,SOCl2reactswithNa2SO3 in a...Ch. 15 - *15.76 The following space-filling model depicts...Ch. 15 - Which of the following compounds is the stronger...Ch. 15 - Which of the two molecules below is the stronger...Ch. 15 - 15.79 Write equations that illustrate the...Ch. 15 - Hydrogen peroxide is a stronger Brnsted-Lowry acid...Ch. 15 - Sodium hydroxide, NaOH, is basic. Aluminum...Ch. 15 - Hydrazine, N2H4, is a weaker Brnsted-Lowry base...Ch. 15 - Identify the two Brnsted-Lowry acids and two bases...Ch. 15 - In the reaction in the preceding exercise, the...Ch. 15 - How would you expect the degree of ionization of...Ch. 15 - Prob. 86RQCh. 15 - A mixture is prepared containing 0.10 M of each of...Ch. 15 - 15.88 Are all Arrhenius acids Brønsted-Lowry...Ch. 15 - How could you determine whether HBr is a stronger...Ch. 15 - 15.90 Alcohols are organic compounds that have an...Ch. 15 - Acid rain, acid mine runoff, and acid leaching of...Ch. 15 - 15.92 Using just Figure 7.30, find the five most...
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- Synthesis of ZybanⓇ: 1. Write a mechanism for the bromination of m-chloropropiophenone. Br₂ CH2Cl2 Cl Br 2. Give the expected m/z (to a round number) for the molecular ion from the product above (including isotopic peaks). 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_forwardSynthesis 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_forward
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- Sodium 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_forwardAspirin 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_forward
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