1. Diels-Alder reaction of furans with alkenes or alkyne dienophiles followed by treatment with mineral acid leads to the formation of benzene derivatives. Predict the structures of A and B, and propose a detailed mechanism of the following reactions. 1. Diels-Alder FOCH3 + A -CO2CH3 2. HзО* ОСНЗ 1. Diels-Alder НС: -CO2CH3 2. H30*

1. Diels-Alder reaction of furans with alkenes or alkyne dienophiles followed by treatment with mineral acid leads to the formation of benzene derivatives. Predict the structures of A and B, and propose a detailed mechanism of the following reactions. 1. Diels-Alder FOCH3 + A -CO2CH3 2. HзО* ОСНЗ 1. Diels-Alder НС: -CO2CH3 2. H30*

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 24MP

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The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.
(a) A compound known to be a substituted cyclohexanone derivative has lamda max of 235 nm. Could this compound be a conjugated dienone? explain (b) (i)For this compound, how many nm must be accounted for by substituents? (ii) What are the substituents and the points of substitution that may occur having accounted for the 20nm?
Draw and discuss the mechanism (with arrows to show electron movements) of the Diels-Alder reaction between anthracene and maleic anhydride. Draw the orientation and phases of the reacting p-orbitals showing how they overlap in a “suprafacial” geometry to form product
Give the structure of the main product of each of the following Diels-Alder reactions. Make sureto show the stereochemistry of the products when unambiguous.
Predict products of each Diels-Alder reaction (including stereochemistry)
Give major products for 1,2-/1,4-additions (A) Diels-Alder (B-D) cycloadditions [2+2] cycloadditions , and Retro-Diels-Alder (E) cycloaddition. Illustrate the regiochemistry and stereochemistry (me so, enatiomer., exo or Endo) for cycloadditions B-D?
Compound MM (g/mol) Volume Used (mL) d (g/mL) Weight Used (g) Moles Used Equivalence 9-anthracenemethanol 208.26 g g/mol N/A N/A 0.065 g (given) 0.0003 (rounded) 1 N-methylmaleimide 111.10 g/mol N/A N/A 0.104 g (given) 0.0003*3 = 0.0009 (rounded) 3 Diels-Alder Adduct/Product 319.4 g/mol N/A N/A 1 Please figure out the theoretical yield and moles of the product based on the table and image.
Diels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO)gives a mixture of products, but the 1,2-disubstituted product oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.
Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(CzHs)3). 3SnCl4 + 4Al(C2H5)3 → 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d= 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?
Qn no. 20. Kindly provide proper explanation with all details for each step.
Please answer both parts to the questions completely. I will rate the answer afterwards. For a diels-alder reaction between anthracene and maleic anhydride, are the exo and endo forms of product 9,10-dihydroanthracene-9,10-ɑ,β-succinic acid anhydride different stereoisomers or are they the same molecule? Explain your answer by drawing the molecule. Would it be favorable to get a 1,4-adduct of anthracene and maleic anhydride? Why or why not? If the 1,4-adduct of anthracene and maleic anhydride had formed, would it have different exo and endo isomers? Yes or no and why?
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