Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 13, Problem 16PP
Practice Problem 13.16
Diels–Alder reactions also take place with triple-bonded (acetylenic) dienophiles. Which diene and which dienophile would you use to prepare the following?
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Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGP
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- The diene lactone shown in part (a) has one electron-donating group (¬OR) and one electron-withdrawing group(C“O). This diene lactone is sufficiently electron-rich to serve as the diene in a Diels–Alder reaction.(a) What product would you expect to form when this diene reacts with methyl acetylenecarboxylate, a strong dienophile?arrow_forwardOne step in the synthesis of dodecahedrane involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.arrow_forwardBased on 1,3_cyclopentadiene,using the necessary organic and inorganic chemicals the synthesis scheme includes the synthesis of the following compound,including the Diel-Alder reaction design.arrow_forward
- Based on 1,3-cyclopentadiene, using the necessary organic and inorganic chemicals. The synthesis scheme includes the synthesis of the following compound, including the Diel-Alder reaction design.arrow_forwardPredict the product of the following Diels-Alder reaction. Make sure to indicate stereochemistry whereverapplicable.arrow_forwardZingiberene and β-sesquiphellandrene, natural products obtained from ginger root, contain conjugated diene units. Which diene reacts faster in the Diels–Alder reaction and why?arrow_forward
- Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.arrow_forwardConversion of an alkene to a halohydrin and internal displacement of a halide ion by an alkoxide ion are both stereoselective. Use this information to demonstrate that the configuration of the alkene is preserved in the epoxide. As an illustration, show that reaction of cis-2-butene by this two-step sequence gives cis-2,3- dimethyloxirane (cis-2-butene oxide).arrow_forwardCompound X is a polyene with absorption in the UV region. Its H-NMR spectrum shows no peak in the region of 7-9 ppm. Compound XIt is not aromatic, nor is it anti aromatic, but it can act chemically as a diene or dienophile in a Diels-Alder reaction.What will be the structure of this well-known compound?arrow_forward
- Hydrocarbon 10 and ester 12 react upon heating to give a cycloaddition product D. (i) Suggest a structure for product D and provide a curved arrow mechanism that accounts for its formation. (ii) Draw the molecular orbitals corresponding to the HOMO of 10 and the LUMO of 12 and show that these are of suitable symmetry for a concerted cycloaddition to take place. (iii) Use frontier molecular orbital theory to account for the observation that the formation of D is faster in the presence of AlCl3. please answer all thank youarrow_forwardA student was given from the list of the compounds below A, B and D blindly and asked to identify them all. He treated each of them with Brady's reagent (2,4-ditrophenylhydrazine) and isolated a bright yellow compound for one of them, but the other two gave false negatives. The student reasoned that the false negatives may be due to sterics and, on further thinking, it dawned on him that he might be able to rule out one of the false negatives with the haloform test. What compound did he find compatible with the haloform test? That compound did indeed give a false negative in the Brady test. Which of the other two was positive in the Brady test? A = haloform B = Brady A = haloform D = Brady B = haloform A = Brady B = haloform D = Brady D = haloform A = Brady D = haloform B = Bradyarrow_forwardThe Diels–Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.arrow_forward
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