CHEMISTRY
2nd Edition
ISBN: 9781593995782
Author: OpenStax
Publisher: XANEDU PUBLISHING
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Textbook Question
Chapter 8, Problem 44E
Which of the period 2 homonuclear diatomic molecules are predicted to be paramagnetic?
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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 8 Solutions
CHEMISTRY
Ch. 8 - Explain how and bonds are similar and how they...Ch. 8 - Draw a curve that describes the energy of a system...Ch. 8 - Explain why bonds occur at specific average bond...Ch. 8 - Use valence bond theory to explain the bonding in...Ch. 8 - Use valence bond theory to explain the bonding in...Ch. 8 - How many and bonds are present in the molecule...Ch. 8 - A friend tells you N2 has three bonds due to...Ch. 8 - Draw the Lewis structures for CO2 and CO, and...Ch. 8 - Why is the concept of hybridization required in...Ch. 8 - Give the shape that describes each hybrid orbital...
Ch. 8 - Explain why a carbon atom cannot form five bonds...Ch. 8 - What is the hybridization of the central atom in...Ch. 8 - A molecule with the formula AB3 could have one of...Ch. 8 - Methionine, CH3SCH2CH2CH(NH2)CO2H, is an amino...Ch. 8 - Sulfuric acid is manufactured by a series of...Ch. 8 - Two important industrial chemicals, ethene, C2H4,...Ch. 8 - For many years after they were discovered, it was...Ch. 8 - Consider nitrous acid, HNO2 (HONO). (a) Write a...Ch. 8 - Strike-anywhere matches contain a layer of KClO3...Ch. 8 - Identify the hybridization of each carbon atom in...Ch. 8 - Write Lewis structures for NF3 and PP5. On the...Ch. 8 - In addition to NF3, two other fluoro derivatives...Ch. 8 - The bond energy of a C—C single bond averages 347...Ch. 8 - For the carbonate ion, CO32, draw all of the...Ch. 8 - A useful solvent that will dissolve salts as well...Ch. 8 - For the molecule allene, H2C=C=CH2, give the...Ch. 8 - Identify the hybridization of the central atom in...Ch. 8 - Describe the molecular geometry and hybridization...Ch. 8 - For each of the following molecules, indicate the...Ch. 8 - For each of the following structures, determine...Ch. 8 - Draw the orbital diagram for carbon in CO2 showing...Ch. 8 - Sketch the distribution of electron density in the...Ch. 8 - How are the following similar, and how do they...Ch. 8 - If molecular orbitals are created by combining...Ch. 8 - Can a molecule with an odd number of electrons...Ch. 8 - Can a molecule with an even number of electrons...Ch. 8 - Why are bonding molecular orbitals lower in energy...Ch. 8 - Calculate the bond order for an ion with this...Ch. 8 - Explain why an electron in the bonding molecular...Ch. 8 - Predict the valence electron molecular orbital...Ch. 8 - Determine the bond order of each member of the...Ch. 8 - For the first ionization energy for an N2...Ch. 8 - Compare the atomic and molecular orbital diagrams...Ch. 8 - Which of the period 2 homonuclear diatomic...Ch. 8 - A friend tells you that the 2s orbital for...Ch. 8 - True or false: Boron contains 2s22p1 valence...Ch. 8 - What charge would be needed on F2 to generate an...Ch. 8 - Predict whether the MO diagram S2 would show s-p...Ch. 8 - Explain why N22+ is diamagnetic, while O24+, which...Ch. 8 - Using the MO diagrams, predict the bond order for...
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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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