CHEMISTRY
2nd Edition
ISBN: 9781593995782
Author: OpenStax
Publisher: XANEDU PUBLISHING
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Chapter 20, Problem 35E
Write the condensed structures of all isomers with the formula C2H5O2. Label the
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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 20 Solutions
CHEMISTRY
Ch. 20 - Write the chemical formula and Lewis structure of...Ch. 20 - What is the difference between the hybridization...Ch. 20 - On a microscopic level, how does the reaction of...Ch. 20 - On a microscopic level, how does the reaction of...Ch. 20 - Explain why unbranched alkenes can form geometric...Ch. 20 - Explain why these two molecules are not isomers:Ch. 20 - Explain why these two molecules are not isomers:Ch. 20 - How does the carbon-atom hybridization change when...Ch. 20 - Write the Lewis structure and molecular formula...Ch. 20 - Write the chemical formula, condensed formula, and...
Ch. 20 - Give the complete IUPAC name for each of the...Ch. 20 - Give the complete IUPAC name for each of the...Ch. 20 - Butane is used as a fuel in disposable lighters....Ch. 20 - Write Lewis structures and name the five...Ch. 20 - Write Lewis structures for the Cis -trans isomers...Ch. 20 - Write structures for the three isomers of the...Ch. 20 - Isooctane is the common name of the isomer of...Ch. 20 - Write Lewis structures and IUPAC names for the...Ch. 20 - Write Lewis structures and IUPAC names for all...Ch. 20 - Name and write the structures of all isomers of...Ch. 20 - Write the structures for all the isomers of the...Ch. 20 - Write Lewis structures and describe the molecular...Ch. 20 - Benzene is one of the compounds used as an octane...Ch. 20 - Teflon is prepared by the polymerization of...Ch. 20 - Write two complete, balanced equations for each of...Ch. 20 - Write two complete, balanced equations for each of...Ch. 20 - What mass of 2-bromopropane could be prepared from...Ch. 20 - Acetylene is a very weak acid; however, it will...Ch. 20 - Ethylene can be produced by the pyrolysis of...Ch. 20 - Why do the compounds hexane, hexanol, and hexane...Ch. 20 - Write condensed formulas and provide IUPAC names...Ch. 20 - Give the complete IUPAC name for each of the...Ch. 20 - Give the complete IUPAC name and the common name...Ch. 20 - Write the condensed structures of both isomers...Ch. 20 - Write the condensed structures of all isomers with...Ch. 20 - Draw the condensed formulas for each of the...Ch. 20 - MTBE, Methyl tert -butyl ether, CH3OC(CH3)3, is...Ch. 20 - Write two complete balanced equations for each of...Ch. 20 - Write two complete balanced equations for each of...Ch. 20 - Order the following molecules from least to most...Ch. 20 - Predict the products of oxidizing the molecules...Ch. 20 - Predict the products of reducing the following...Ch. 20 - Explain why it is not possible to possible a...Ch. 20 - How does hybridization of the substituted carbon...Ch. 20 - Fatty acids are carboxylic acids that have long...Ch. 20 - Write a condensed structural formula, such as...Ch. 20 - Write a condensed structural formula, such as...Ch. 20 - The foul odor of rancid butter is caused by...Ch. 20 - Write the two-resonance structures for the acetate...Ch. 20 - Write two complete, balanced equations for each of...Ch. 20 - Write two complete balanced equations for each of...Ch. 20 - Yields in organic reactions are sometimes low....Ch. 20 - Alcohols A, B and C all have the composition C4H...Ch. 20 - Write the Lewis structures of both isomers with...Ch. 20 - What is the molecular structure about the nitrogen...Ch. 20 - Write the two resonance structures for the...Ch. 20 - Draw Lewis structures for pyridine and its...Ch. 20 - Write the Lewis structures of all isomers with the...Ch. 20 - Write two complete balanced equations for the...Ch. 20 - Write two complete, balanced equations for each of...Ch. 20 - Identify any carbon atoms that change...Ch. 20 - Identify any carbon atoms that change...Ch. 20 - Identify any carbon atoms that change...
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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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