EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Chapter 16.8A, Problem 16.11P
Repeat Problem16-10 for the cyclopentadienyl ions. Draw one all-bonding MO, then a pair of degenerate MOs, and then a final pair of degenerate MOs. Draw the energy diagram, fill in the electrons, and confirm the electronic configurations of the cyclopentadienyl cation and anion.
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5. Draw all five pi Molecular Orbitals of the cyclopentadienyl cation using appropriate
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anti bonding interactions. Label each MO as either bonding, non-bonding or antibonding.
Show how the four pi electrons occupy the lowest energy MOs. Repeat with cyclopentadienyl
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*
= + or. or -
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Which a molecular orbitals are symmetric?
Which t molecular orbitals are antisymmetric?
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Chapter 16 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw the energy diagram for cyclooctatetraene dianion , C8H8 (2-) , molecular orbitals. The polygon rule is helpful. Label each MO as bonding , antibonding, or nonbonding, and add the nonbonding line. Identify the LOMO, HOMO, LUMO and HUMO orbitals. Is this dianion aromatic , non aromatic or anti aromatic? Thank you!arrow_forward5. Draw all five pi Molecular Orbitals of the cyclopentadienyl cation using appropriate shading. Indicate the relative energies of each MO by analyzing the number of bonding and anti bonding interactions. Label each MO as either bonding, non-bonding or antibonding. Show how the four pi electrons occupy the lowest energy MOs. Repeat with cyclopentadienyl radical (5 pi electrons) and cyclopentadienyl anion ( 6 pi electrons). Label the cyclopentadienyl cation, radical and anion as either aromatic, non aromatic or anti-aromatic. * = + or.or -arrow_forwardDraw the structure of (Z)-2,3-dichloro-4-methyl-2-hexene. Consider E/Z stereochemistry of alkenes. • You do not have to explicitly draw H atoms. opy aste C ChemDoodlearrow_forward
- The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms. How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?arrow_forwardWhat types of orbitals overlap to provide stability to the tert-butyl carbocation ((Ch3) 3C +) by hyperconjugation: a. 2p atomic orbital of tertiary carbon plus sp2 atomic orbital of tertiary carbo b. 2p atomic orbital of tertiary carbon plus sigma C-H molecular orbital of methyl c.2p atomic orbital of tertiary carbon plus 2s C-h atomic orbital of methyl d. sp2 atomic orbital of tertiary carbon plus sigma C-H molecular orbital of methyl.arrow_forwardWhich of the following molecular orbital diagram best represents the ground state of the cyclopentadiene molecule? Energy A - - B - - G # - G+ G + S - -arrow_forward
- Which one of the following represents the HOMO of 1,3-butadiene in the ground State?arrow_forwardDiels—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 often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forwardThe pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energyarrow_forward
- The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpairedelectron onto three carbon atoms.(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atomsshare the positive charge? Does this picture agree with the resonance picture?(h) Add an…arrow_forwardDraw the structure of the product of the Diels-Alder reaction below. CH3 a CH3 CH3OC-C=C-COCH3 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. / • If a group is achiral, do not use wedged or hashed bonds on it. • If the reaction produces a racemic mixture, just draw one stereoisomer. O. Sn » [ ]# ?arrow_forwardThe most stable MO of 1,3,5-hexatriene and the most stable MO of benzene Which compound is more stable? Why?arrow_forward
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