Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305082144
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 11.SE, Problem 36MP
Interpretation Introduction
Interpretation:
The mechanism has to be proposed and the experimental evidence has to be discussed.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
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 11 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
Ch. 11.1 - Prob. 1PCh. 11.2 - Prob. 2PCh. 11.2 - Prob. 3PCh. 11.3 - Prob. 4PCh. 11.3 - Prob. 5PCh. 11.3 - Rank the following compounds in order of their...Ch. 11.3 - Organic solvents like benzene, ether, and...Ch. 11.4 - Prob. 8PCh. 11.4 - Prob. 9PCh. 11.4 - Prob. 10P
Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
Knowledge Booster
Similar questions
- 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
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT