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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5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.
Isoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 mol of hydrogen bromide to isoprene to give 1,3-dibromo-3-methylbutane.Write a series of equations describing the mechanism of this reaction.
The sex attractant of the common housefly is a hydrocarbon named muscalure, C23H46. On treatment of the muscalure with aqueous acidic KMnO4, two products are obtained, CH3(CH2)12CO2H and CH3(CH2)7CO2H. Propose a structure for the muscalure.
Please provide a full explanation with steps when providing the structure as a response, thank you!
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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- Propose a mechanism for the biosynthesis of the sesquiterpenoid trichodiene from farnesyl diphosphate. The process involves cyclization to give an intermediate secondary carbocation, followed by several carbocation rearrangements.arrow_forwardAmines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.arrow_forward4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.arrow_forward
- Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct. Can be more than one answerarrow_forwardGrignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.arrow_forwardCompound A, C9H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment. What is the structure for A?arrow_forward
- a) Reaction of 2-methyl propene with methanol in acid-catalyzed medium step by step showing the mechanism, show the product to be formed. b) Starting from benzene, synthesize the following substances by choosing the appropriate reagents. 1) m-chloro benzoic acid 2) p-nitro phenolarrow_forwardFollowing is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.arrow_forwardBenzyl bromide is converted into benzaldehyde by heating in dimethyl sulfoxide. Propose a structure for the intermediate, and show the mechanisms of the two steps in the reaction.arrow_forward
- Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forwardIt is not uncommon for organic chemists to prepare acetals by an exchange-type process known as transacetalization. Predict the product(s) and show the mechanism for the transacetalization reactions below.arrow_forwardThe pyrolysis of acetic esters to give an alkene and acetic acid is thought to involve a planar transition state and cyclic redistribution of (4n + 2) electrons. Propose a mechanism for pyrolysis of the following ester.arrow_forward
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