Chemistry For Today: General, Organic, And Biochemistry, Loose-leaf Version
9th Edition
ISBN: 9781305968707
Author: Spencer L. Seager
Publisher: Brooks Cole
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Textbook Question
Chapter 5, Problem 5.62E
Rewrite the following word equation using chemical formulas. Balance the equation and write the balanced equation in net ionic form:
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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.
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?
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?
Chapter 5 Solutions
Chemistry For Today: General, Organic, And Biochemistry, Loose-leaf Version
Ch. 5 - Identify the reactants and products in each of the...Ch. 5 - Identify the reactants and products in each of the...Ch. 5 - Prob. 5.3ECh. 5 - Identify which of the following are consistent...Ch. 5 - Prob. 5.5ECh. 5 - Determine the number of atoms of each element on...Ch. 5 - Balance the following equations: a....Ch. 5 - Balance the following equations: a....Ch. 5 - Assign oxidation numbers to the blue element in...Ch. 5 - Assign oxidation numbers to the blue element in...
Ch. 5 - Find the element with the highest oxidation number...Ch. 5 - Find the element with the highest oxidation number...Ch. 5 - For each of the following equations, indicate...Ch. 5 - For each of the following equations, indicate...Ch. 5 - Assign oxidation numbers to each element in the...Ch. 5 - Assign oxidation numbers to each element in the...Ch. 5 - The tarnish of silver objects is a coating of...Ch. 5 - Prob. 5.18ECh. 5 - Prob. 5.19ECh. 5 - Classify each of the reactions represented by the...Ch. 5 - Classify each of the reactions represented by the...Ch. 5 - Prob. 5.22ECh. 5 - Prob. 5.23ECh. 5 - Prob. 5.24ECh. 5 - Prob. 5.25ECh. 5 - Prob. 5.26ECh. 5 - Prob. 5.27ECh. 5 - Consider all of the following ionic compounds to...Ch. 5 - Consider all of the following ionic compounds to...Ch. 5 - Prob. 5.30ECh. 5 - Reactions represented by the following equations...Ch. 5 - Prob. 5.32ECh. 5 - Prob. 5.33ECh. 5 - Prob. 5.34ECh. 5 - Prob. 5.35ECh. 5 - Prob. 5.36ECh. 5 - Prob. 5.37ECh. 5 - Prob. 5.38ECh. 5 - Prob. 5.39ECh. 5 - Prob. 5.40ECh. 5 - Calculate the number of grams of SO2 that must...Ch. 5 - Calculate the mass of limestone (CaCO3) that must...Ch. 5 - Calculate the number of moles of CO2 generated by...Ch. 5 - Calculate the number of grams of bromine (Br2)...Ch. 5 - Prob. 5.45ECh. 5 - Prob. 5.46ECh. 5 - Pure titanium metal is produced by reacting...Ch. 5 - An important metabolic process of the body is the...Ch. 5 - Caproic acid is oxidized in the body as follows:...Ch. 5 - A sample of 4.00g of methane (CH4) is mixed with...Ch. 5 - Nitrogen and oxygen react as follows:...Ch. 5 - Suppose you want to use acetylene (C2H2) as a...Ch. 5 - Ammonia, carbon dioxide, and water vapor react to...Ch. 5 - Prob. 5.55ECh. 5 - The actual yield of a reaction was 11.74g of...Ch. 5 - A product weighing 14.37g was isolated from a...Ch. 5 - Prob. 5.58ECh. 5 - A sample of calcium metal with a mass of 2.00g was...Ch. 5 - Upon heating, mercury (II) oxide undergoes a...Ch. 5 - Prob. 5.61ECh. 5 - Rewrite the following word equation using chemical...Ch. 5 - The element with an electron configuration of...Ch. 5 - Assuming a 100 reaction yield, it was calculated...Ch. 5 - The decomposition of a sample of a compound...Ch. 5 - Prob. 5.66ECh. 5 - Prob. 5.67ECh. 5 - Prob. 5.68ECh. 5 - Prob. 5.69ECh. 5 - Prob. 5.70ECh. 5 - Certain vegetables and fruits, such as potatoes...Ch. 5 - In an ordinary flashlight battery, an oxidation...Ch. 5 - Prob. 5.73ECh. 5 - Prob. 5.74ECh. 5 - Which of the following equations is balanced? a....Ch. 5 - Prob. 5.76ECh. 5 - Prob. 5.77ECh. 5 - What is the oxidation number of sodium in the...Ch. 5 - Prob. 5.79ECh. 5 - Prob. 5.80ECh. 5 - Prob. 5.81ECh. 5 - Prob. 5.82ECh. 5 - Prob. 5.83ECh. 5 - Which of the following species is being oxidized...Ch. 5 - Identify the oxidizing agent and the reducing...Ch. 5 - Prob. 5.86ECh. 5 - Identify the following as an oxidation, a...Ch. 5 - Prob. 5.88ECh. 5 - Prob. 5.89ECh. 5 - Prob. 5.90ECh. 5 - What is the net ionic equation of the following...Ch. 5 - Prob. 5.92ECh. 5 - Prob. 5.93ECh. 5 - The number of grams of hydroegn formed by the...Ch. 5 - In the reaction CaCl2+Na2CO3CaCO3+2NaCl, if...Ch. 5 - Prob. 5.96E
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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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