Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 43P
Draw all of the
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Show how to construct the molecular orbitals of ethylene, butadiene, and the allylicsystem. Show the electronic configurations of ethylene, butadiene, and the allylcation, radical, and anion.
How would you draw a molecular orbital diagram of butadiene showing the energies and occupancy ofthe orbitals in the ground state? How would you estimate the total pi binding energy of the molecule?
For the B 2H 6 molecule
i) Using projection operators, derive a set of SALCs using the bridging H 1s orbitals.
ii) Using projection operators, derive a set of SALCs using the s- and p- orbitals of the B atoms.
iii) Using the SALCs derived in (i) and (ii), draw a molecular orbital diagram for the interaction between the B atoms and the bridging H atoms.
iv) Fill in the molecular orbital diagram from (iii), remembering that 8 of the available electrons will be used in the bonds between the B atoms and the terminal H atoms – those will not show up in this diagram.
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGP
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- Three of the four molecular orbitals for cyclobutadiene are pictured here. Place them in order of increasing energy. (See Figures 9.13, 9.15, 9.16, and 9.18 and the relation of orbital energy and nodes.)arrow_forwardThe FEMO theory of conjugated molecules is crude and marginally better results are obtained with simple Huckel theory. (a) For a linear conjugated polyene with each of N carbon atoms contributing an electron in a 2porbital, the energies Ek of the resulting π molecular orbitals are given by: Ek = α + 2β cos kπ/N+1 k = 1,2,3, ... N Use this expression to estimate the resonance integral β for the series consisting of ethene, butadiene, hexatriene, and octatetraene given that ult raviolet absorptions from the HOMO, which is a bonding π orbital, to the LUMO, which is an antibonding π* orbital, occur at 61 500, 46 080, 39 750,and 32 900 cm- 1, respectively. (b) Calculate the π-electron delocalization energy, Edelcc = Eπ -n(α + β). of octatetraene, where Eπ, is the total π-electron binding energy and n is the total number of π-electrons.arrow_forwardWhich MOs are the HOMO and the LUMO in the ground state? for the MOs of 1,3,5-hexatrienearrow_forward
- How many anti-bonding pi-type molecular orbitals does 1,3-butadiene contain?arrow_forwardH-He-H2+ is a linear trinuclear with He occupying the central position and the two hydrogen occupying the terminal positions. Build a reasonable qualitative molecular orbital diagramarrow_forwardDraw a 3D representation of the molecule penta-1,2,3,4-tetraene using the following EXPLICIT instructions: sigma bonds in the plane of the paper are normal lines, sigma bonds or orbitals projecting in front of the page are heavy lines, sigma bonds or orbitals projecting behind the page are dashed lines, and pi bonds are shown by drawing the lobes of the p-orbitals and indicating the overlaps. What is the hybridization of each atom (except H) in this molecule?arrow_forward
- The molecule shown on the right in the example in the right column is the amino acid histidine, and the five-membered ring is known as aromatic. An aromatic ring has 2, 6, 10, 14, etc., electrons placed in 2p orbitals around a ring. Indicate which of the following statements must therefore be true. 1. There are a total of six electrons in the pi system (defined as electrons in 2p orbitals), including the lone pair on the ring N that is not circled. 2. There are a total of six electrons in the pi system, including the lone pair on the ring N atom that is circled. 3. The lone pair on the ring N atom that is not circled resides in an sp2 orbital on an sp2 hybridized nitrogen atom. 4. Statements 2 and 3 are both truearrow_forwardSketch the ultraviolet absorption spectrum of 1,3-Butadiene, matching peaks to electronic transitions. show that four isolated p orbital on carbon atoms combine to form pi orbitalarrow_forwardConstruct the molecular-orbital energy level diagramsof (a) ethene and (b) ethyne on the basis that the moleculesare formed from the appropriately hybridized CH2 or CH fragmentsarrow_forward
- Which MOs are the HOMO and the LUMO in the excited state? for the MOs of 1,3,5-hexatriene:arrow_forwardExplain why a molecule with no dipole moment is microwave inactive but may show an infrared spectrum.Which of the following molecules may show infrared absorption spectra and, in each case, briefly explain why this is so: (i) H2, (ii) HCl, (iii) CO2 , and (iv) H2O?arrow_forwardHow many nodes are there in each of the MOs of 1,3-butadiene?arrow_forward
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