Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 20, Problem 20.28P
Write the frontier molecular orbital analysis for the cycloaddition of butadiene with butadiene when both interact in a suprafacial manner. Is this reaction allowed?
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The longest wavelength electronic transition in simple unsaturated hydrocarbons corresponds to a transition from the highest occupied molecular orbita l (HOMO) to the lowest unoccupied molecular orbita l (LUMO) . Predict the energy of the HOMO to LUMO separation in (a) ethane. (b) butadiene. and (c) benzene.
(i) Unsolvated methyllithium and tert-butyllithium have similar solid-state
structures. Explain the multicentre covalent bonding in these structures. Use
diagrams of orbitals where necessary and construct a molecular orbital
diagram.
(ii) tert-butyllithium is soluble in non-polar alkane solvents but methyllithium is
insoluble in non-polar alkane solvents. Explain this observation.
Explain and give examples of the stability order of carbocations within the group and among different groups
Chapter 20 Solutions
Organic Chemistry
Ch. 20.1 - Prob. 20.1PCh. 20.1 - Estimate the stabilization gained as a result of...Ch. 20.2 - Predict the product(s) formed by addition of one...Ch. 20.3 - Prob. 20.4PCh. 20.3 - Prob. 20.5PCh. 20.4 - Prob. 20.6PCh. 20.5 - Prob. 20.7PCh. 20.5 - Prob. 20.8PCh. 20.5 - Prob. 20.9PCh. 20.6 - Prob. 20.10P
Ch. 20.6 - Prob. 20.11PCh. 20.6 - Prob. 20.12PCh. 20 - If an electron is added to 1,3-butadiene, into...Ch. 20 - Prob. 20.15PCh. 20 - Predict the structure of the major product formed...Ch. 20 - Predict the major product formed by 1,4-addition...Ch. 20 - Predict the structure of the major 1,2-addition...Ch. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Pyridine exhibits a UV transition of the type n at...Ch. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Write the frontier molecular orbital analysis for...Ch. 20 - Prob. 20.29PCh. 20 - Draw structural formulas for the products of...Ch. 20 - Propose structural formulas for compounds A and B...Ch. 20 - Under certain conditions, 1,3-butadiene can...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - The following triene undergoes an intramolecular...Ch. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - The Diels-Alder reaction is not limited to making...Ch. 20 - The first step in a synthesis of dodecahedrane...Ch. 20 - Bicyclo-2,5-heptadiene can be prepared in two...Ch. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Following is a retrosynthetic scheme for the...Ch. 20 - Prob. 20.46PCh. 20 - Prob. 20.47PCh. 20 - Prob. 20.48PCh. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - What reaction presented in this chapter is...Ch. 20 - Claisen rearrangement of an allyl phenyl ether...Ch. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - We now continue the use of organic chemistry...Ch. 20 - Write the products of the following sequences of...
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- When considering the photochemical cis-trans isomerization of trans-stilbene, an electrocyclization is observed. The product of this electrocyclization is usually oxidized to a condensed aromatic product (by oxygen or addition of other oxidizing reagents such as iodine). Discuss the mechanism of electrocyclic ring formation and ring opening non- verbally by showing orbital images, indicate the orientation of the cyclization / opening, and shoe how this reaction is crucial in the synthesis of helicenes.arrow_forwardElucidate the structure, hybridization, stability order and factors affecting the stability of an organic intermediate which is formed by the homolytic bond breaking.arrow_forward(3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_forward
- . Predict the orientation in each of the following reactions, giving structural formulas for the predicted products: (a) 1-methylnaphthalene + Brz (b) 1-methylnaphthalene + HNO3 + H2SO4 (c) 1-methylnaphthalene + CH3COCI + AICI3 (d) the same as (a), (b), and (c) for 2-methylnaphthalene (e) 2-nitronaphthatene + Brz (f) 2-methoxynaphthalene + Brzarrow_forward(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.arrow_forwardInterpret the acidity of alcohols on the basis of ground-state polarization and stability of the alcoholate anion(indicate and give symbols for bond polarization)! Compare the relative acidity of ethanol and 2-fluoroethanol!arrow_forward
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- Classify the following dienes and polyenes as isolated, conjugated, cumulated, or some combination of theseclassifications.(a) cycloocta-1,4-dienearrow_forwardOrganometallic reagents are useful synthetically because they react as if they were free : : that is, carbon bears a partial charge, and here is a partial * charge on Mg-X, where X is a halogen.arrow_forward(c) Diels-Alder reactions are a highly effective way to synthesise stereospecifically fused cyclic structures. (1) Using suitable diagrams, curly arrows and/or reaction schemes, explain why the reaction between cyclopentadiene and maleic anhydride favours formation of the endo product. (ii) If the reaction in part (i) were conducted using furan instead of cyclopentadiene, what difference would you observe in the product/s, with respect to their stereochemistry? (No need to draw reaction mechanisms) (iii) Draw the stereospecific 3D structure of the product formed during the Diels-Alder reaction below. (No need to show the reaction mechanism) Нeat Br Br (Figure Q11ciii)arrow_forward
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