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(a)
Interpretation:
An orbital symmetry analysis for showing the suprafacial
Concept introduction:
The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a
(b)
Interpretation:
The type of sigmatropic reactions that is involved in the given reactions is to be stated. Whether the stereochemistry of the first step is according to the predictions of orbital symmetry or not is to be stated.
Concept introduction:
The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a
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Chapter 28 Solutions
EBK ORGANIC CHEMISTRY
- 6) (a) State with reasons whether the following compounds are aromatic, antiaromatic, or nonaromatic (1) HC=C=CH NH NH (iii) (iv) (b) Which is more stable, cyclobutadiene or 1,3-butadiene? Explain. ( (v)arrow_forwardWrite the frontier molecular orbital analysis for the cycloaddition of butadiene with butadiene when both interact in a suprafacial manner. Is this reaction allowed?arrow_forward(1) (ii) (iii) (iv) (v) What is the relationship between the compounds [Cl-Ag-SCN]™ and [SCN-Ag-CIJ? Name the compounds whose molecular formulae are given in Question 1(a) (i). Which of the compounds, [Cl-Ag-SCN] and [SCN-Ag-CI], is the more stable? Explain your answer. Draw the boundary surfaces of all 3d orbitals and label these orbitals according to the conventional nomenclature. Clearly draw and label the Cartesian axes. Draw the crystal field splitting diagram for a linear compound, e.g. [Cl-Ag-SCN] or [SCN-Ag-CI], aligned along the z-axis. You only need to indicate the order of the individual d orbitals as a function of the energy. Explain your answer.arrow_forward
- (a) Write the structures of the following compounds and mark them as chiral or achiral. 4 (i) 2-Bromopentane (ii) 3-Bromopentane (iii) 1-Bromo-2-methylbutane (iv) 2-Chloro-3-methylbutane (b) Identify the asymmetric carbon in the chiral compounds. (c) Write the structure of the other enantiomer of the chiral compounds.arrow_forwardFuran undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuranarrow_forwardDraw the structures of the two linkage isomers; include representations of the resonance forms of the NO2- Explain the origin of and the differences in the position of both absorption maxima in the UV-visible spectra of the two isomers. Studies have shown the isomerization to be an intramolecular process. Comment on a possible mechanism. Draw a possible transition state for the isomerization process.arrow_forward
- Show how to construct themolecular orbitals of a conjugatedcyclic system similar to benzene andcyclobutadienearrow_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_forward1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.arrow_forward
- (a) Draw all other stereoisomers of the molecule , labelling meso forms (if any), and assign descriptors to chiral carbon atoms. (b) Including molecule below, label pairs of enantiomers and pairs of diastereomers. (c) If you were to distill a mixture of all the isomers, how many fractions could be obtained, and what is in each fraction?arrow_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_forwardDescribe the conformation of rings A, B, C, and D in cholestanol.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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