Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Videos
Textbook Question
Chapter 14, Problem 43P
Draw all of the
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
How many p2p molecular orbitals are there in anthracene? Answer with ONLY an
integer.
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.
TOPIC: QUANTUM, ATOMIC AND MOLECULAR PHYSICIS
(a) Using Hückel's method, describe the energy of the molecular orbitals T of cyclobutadiene C4H4,
which is a flat molecule made up of a square ring of carbons, as shown in the figure;
(b) Do the same for 1,3-butadiene C4H6, which is an elongated planar molecule, as shown in the figure.
(c) In both cases, draw an energy diagram indicating the filling of the orbitals and identifying the HOMO and the LUMO. Sketch by hand
schematically (using two colors to distinguish the lobes from the 2pz orbitals) the result obtained for the orbitals, identifying them with
the corresponding energy. If possible, you can use the Orbital Viewer program to plot the orbitals.
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
Additional Science Textbook Solutions
Find more solutions based on key concepts
Which of the roll owing compounds have a dipole moment of zero?
Organic Chemistry
a. Draw the resonance forms for SO2 (bonded OSO). b. Draw the resonance forms for ozone (bonded OOO). c. Sulfur...
Organic Chemistry (9th Edition)
6.1 State the number of electrons that be must be lost by atoms of each of the following to achieve a stable el...
Chemistry: An Introduction to General, Organic, and Biological Chemistry (13th Edition)
Fission the splitting of nuclei, and fusion, the combining of nuclei, both release tremendous amounts of energy...
Chemistry: Matter and Change
An engine oil cooler consists of a bundle of 25 smooth tubes, each of length L=2.5m and diameter D=10mm (a) If ...
Fundamentals of Heat and Mass Transfer
What reagents would you use to achieve the following transformation:
Organic Chemistry As a Second Language: Second Semester Topics
Knowledge Booster
Learn more about
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
- 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_forwardConsidering only the molecular orbitals formed by combinations of the 2s atomic orbitals, how many molecular orbitals can be formed by 1000 Li atoms? In the lowest energy state, how many of these orbitals will be populated by pairs of electrons and how many will be empty?arrow_forwardSuppose that a molecular orbital has the (unnormalized) form 0.727A + 0.144B. Find a linear combination of the orbitals A and B that is orthogonal to this combination and determine the normalization constants of both combinations using S = 0.117. Show full and complete procedure, indicating where and how you are using the value of Sarrow_forward
- Show the secular determinant with x substitution for the compound. Calculate its Huckel Molecular orbital levels, wave function, as well as the electron density and bond orders of all carbons.arrow_forwardFor monocyclic conjugated polyenes (such as cyclobutadiene and benzene) with each of N carbon atoms contributing an electron in a 2p orbital, Huckel theory gives the fol lowing expression for the energies Ek of the resulting π molecular orbitals Calculate the energies of the 1t molecular orbitals of benzene and cyclooctatetraene. Comment on the presenceor absence of degenerate energy levels. (b) Ca lcu late and compare the delocalization energies of benzene and hexatriene using the expression from the preceding problem. What do you conclude from your results? (c) Calculate and compare the delocalization energies of cyclooctatetraeneand (linear) octatetraene. Are your conclusions for th is pair of molecules the same as for the pair of molecules investigated in part (b)?arrow_forwardDraw the π-molecular orbitals for benzene, indicate the nodal planes and designate the proper energy corresponding to these orbitals.arrow_forward
- Calculate the Hückel molecular orbital energies of the planar radical (i.e., one nonpaired electron) CH2CHCH2•.Derivethe molecular wavefunction and sketch the molecular orbitals for the lowest energy state. Hint:LCAO-MO principle, use p"(i=1-3) as atomic orbitals.What is the first/minimal electronic excitation energy? Hint:HOMO to LUMO transition.arrow_forwardProvide a diagram which depicts the relative energies of the pi molecular orbitals of benzene. Show which molecular orbitals are filled in benzene's ground state.arrow_forwardDeduce the parities of the six π-orbitals of benzene.arrow_forward
- How do you write the Huckel determinant for the pi electrons of butadiene? How would you find the energies of the molecular orbitals?arrow_forward4. Sketch the Hückel molecular orbitals for 1,3,5-hexatriene. Be sure to identify the HOMO and LUMO levels, the number of nodes present at each psi level, and the electrons present in each orbital. 1,3,5-hexatrienearrow_forwardSet up the secular determinants for the homologous series consisting of ethene, butadiene, hexatriene, and octatetraene and diagonalize them by using mathematical software. Use your results to show that the π molecular orbitals of linear polyenes obey the following rules: • The π molecular orbital with lowest energy is delocalized over all carbon atoms in the chain. • The number of nodal planes between C2p orbitals increases with the energy of the π molecular orbital.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Chemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Linear Combination of Atomic Orbitals LCAO; Author: Edmerls;https://www.youtube.com/watch?v=nq1zwrAIr4c;License: Standard YouTube License, CC-BY
Quantum Molecular Orbital Theory (PChem Lecture: LCAO and gerade ungerade orbitals); Author: Prof Melko;https://www.youtube.com/watch?v=l59CGEstSGU;License: Standard YouTube License, CC-BY