Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 31.SE, Problem 16MP
The polyurethane foam used for home insulation uses methane-diphenyldiisocyanate (MDI) as monomer. The MDI is prepared by acid-catalyzed reaction of aniline with formaldehyde, followed by treatment with phosgene, COCl2. Propose mechanisms for both steps.
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Chapter 31 Solutions
Organic Chemistry
Ch. 31.1 - Order the following monomers with respect to their...Ch. 31.1 - Order the following monomers with respect to their...Ch. 31.1 - Prob. 3PCh. 31.2 - Prob. 4PCh. 31.2 - Prob. 5PCh. 31.3 - Prob. 6PCh. 31.3 - Prob. 7PCh. 31.4 - Prob. 8PCh. 31.4 - Show the mechanism of the nucleophilic addition...Ch. 31.5 - Prob. 10P
Ch. 31.6 - Prob. 11PCh. 31.6 - Prob. 12PCh. 31.SE - Prob. 13VCCh. 31.SE - Prob. 14VCCh. 31.SE - Prob. 15MPCh. 31.SE - The polyurethane foam used for home insulation...Ch. 31.SE - Prob. 17MPCh. 31.SE - Prob. 18MPCh. 31.SE - Prob. 19MPCh. 31.SE - Identify the monomer units from which each of the...Ch. 31.SE - Prob. 21APCh. 31.SE - Draw the structure of Kodel, a polyester prepared...Ch. 31.SE - Show the structure of the polymer that results...Ch. 31.SE - Prob. 24APCh. 31.SE - Prob. 25APCh. 31.SE - 1, 3-Cyclopentadiene undergoes thermal...Ch. 31.SE - Prob. 27APCh. 31.SE - Prob. 28APCh. 31.SE - Prob. 29APCh. 31.SE - Prob. 30APCh. 31.SE - Prob. 31APCh. 31.SE - Prob. 32APCh. 31.SE - Prob. 33APCh. 31.SE - Prob. 34APCh. 31.SE - Prob. 35AP
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- 19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+arrow_forwardLi+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water? Group of answer choices LiBr LiI LiF LiClarrow_forwardQ4: Write organic product(s) of the following reactions and show the curved-arrow mechanism of the reactions. Br MeOH OSO2CH3 MeOHarrow_forward
- Provide the correct IUPAC name for the compound shown here. Reset cis- 5- trans- ☑ 4-6- 2- 1- 3- di iso tert- tri cyclo sec- oct but hept prop hex pent yl yne ene anearrow_forwardQ6: Predict the major product(s) for the following reactions. Note the mechanism (SN1, SN2, E1 or E2) the reaction proceeds through. If no reaction takes place, indicate why. Pay attention to stereochemistry. NaCN DMF Br σ Ilm... Br H Br H H NaCN CH3OH KOtBu tBuOH NaBr H₂O LDA Et2O (CH3)2CHOH KCN DMSO NaOH H₂O, A LDA LDA Systemarrow_forwardQ7: For the following reactions, indicate the reaction conditions that would provide the indicated product in a high yield. Note the major reaction pathway that would take place (SN1, SN2, E1, or E2) Note: There may be other products that are not shown. There maybe more than one plausible pathway. Br H3C OH H3C CI ... H3C SCH2CH3 CI i SCH2CH3 ཨ་ Br System Settarrow_forward
- Q2: Rank the compounds in each of the following groups in order of decreasing rate of solvolysis in aqueous acetone. OSO2CF3 OSO2CH3 OH a. b. CI Brarrow_forwardох 4-tert-butyl oxy cyclohex-1-ene Incorrect, 1 attempt remaining The systematic name of this compound classifies the -OR group as a substituent of the hydrocarbon, which is considered the principal functional group. The ether substituent is named with the suffix 'oxy'. The general format for the systematic name of a hydrocarbon is: [prefix/substituent] + [parent] + [functional group suffix] Substituents are listed in alphabetical order. Molecules with a chiral center will indicate the absolute configuration at the beginning of its name with the R and S notation.arrow_forward5. Compressibility (6 points total). The isothermal compressibility is a measure of how hard/easy it is to compress an object (how squishy is it?) at constant temperature. It is др defined as Br=-()=-(200²)T' (a) You might wonder why there is a negative sign in this formula. What does it mean when this quantity is positive and what does it mean when this quantity is negative? (b) Derive the formula for the isothermal compressibility of an ideal gas (it is very simple!) (c) Explain under what conditions for the ideal gas the compressibility is higher or lower, and why that makes sense.arrow_forward
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