Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
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Chapter 3, Problem 59EQ
Interpretation Introduction
Interpretation: The mechanism with supply arrows and product must be drawn for the base catalysed hydrolysis of a nitrile.
Concept introduction: Hydrolysis is a
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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?
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?
Chapter 3 Solutions
Pushing Electrons
Ch. 3 - Prob. 1EQCh. 3 - Prob. 2EQCh. 3 - Prob. 3EQCh. 3 - Prob. 4EQCh. 3 - Prob. 5EQCh. 3 - Prob. 6EQCh. 3 - Here are some exercises in sigma bond breaking....Ch. 3 - Prob. 8EQCh. 3 - Prob. 9EQCh. 3 - Prob. 10EQ
Ch. 3 - Prob. 11EQCh. 3 - Prob. 12EQCh. 3 - Prob. 13EQCh. 3 - Prob. 14EQCh. 3 - Prob. 15EQCh. 3 - Prob. 16EQCh. 3 - Prob. 17EQCh. 3 - Prob. 18EQCh. 3 - Prob. 19EQCh. 3 - Prob. 20EQCh. 3 - Prob. 21EQCh. 3 - Prob. 22EQCh. 3 - Prob. 23EQCh. 3 - Prob. 24EQCh. 3 - Prob. 25EQCh. 3 - Prob. 26EQCh. 3 - Prob. 27EQCh. 3 - Prob. 28EQCh. 3 - Prob. 29EQCh. 3 - Prob. 30EQCh. 3 - The reaction just described is reversible....Ch. 3 - Prob. 32EQCh. 3 - Prob. 59EQ
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- Acid 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_forwardPlease complete these blanks need that asaparrow_forward
- Nitration 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_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_forward
- Synthesis 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_forwardDraw out the SALCs of wach orbital in a AlCl3 molecule.arrow_forward
- Which of the following is 3-ethyl-2-methylpentane? хarrow_forwardCan you please help me with this problem and explain it step by step? I'm so confused about itarrow_forward2. Identify the reagents you would need to achieve the following. You may need to consider using a protecting group. HO 1. 2. 3. 4. 5. OH Br HOarrow_forward
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