ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 25.2, Problem 3P
(a) Using Figure 27.2 as a guide, draw the molecular orbitals for hexa
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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
The bond length of the indicated C-C single bond in hexa-1,3,5-triene is about
146 pm, which is considerably shorter than that in ethane, H3C-CH3.
(a) How much shorter is it? Hint: See Figure 14-2, page 685.
(b) Which occupied T MOS (obtained in Problem 14.32) help decrease this bond length?
(c) If an electron were promoted from the HOMO to the LUMO, would the length of the
C-C single bond increase, decrease, or stay roughly the same? Explain.
146 pm
Which I molecular orbital represents the ground state HOMO of 1,3,5-hexatriene? Click on a letter A to D to answer.
A
B
Chapter 25 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)
Ch. 25.1 - Prob. 1PCh. 25.2 - Problem 27.2
For each molecular orbital in Figure...Ch. 25.2 - Problem 27.3
(a) Using Figure 27.2 as a guide,...Ch. 25.3 - Prob. 4PCh. 25.3 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.3 - Prob. 8PCh. 25.3 - Prob. 9PCh. 25.3 - Problem 27.11
What product would be formed by the...
Ch. 25.4 - Consider cycloheptatrienone and ethylene, and draw...Ch. 25.4 - Problem 27.13
Show that a thermal suprafacial...Ch. 25.4 - Prob. 13PCh. 25.5 - Prob. 17PCh. 25.5 - Prob. 18PCh. 25.5 - Prob. 19PCh. 25.5 - Prob. 20PCh. 25.5 - Prob. 21PCh. 25.5 - Prob. 22PCh. 25.5 - Problem 27.25
(a) What product is formed by the...Ch. 25.6 - Prob. 24PCh. 25 - Prob. 25PCh. 25 - Prob. 26PCh. 25 - Prob. 31PCh. 25 - Prob. 32PCh. 25 - Prob. 33PCh. 25 - Prob. 34PCh. 25 - Prob. 35PCh. 25 - Prob. 36PCh. 25 - Prob. 37PCh. 25 - Prob. 41PCh. 25 - Prob. 42PCh. 25 - Prob. 44PCh. 25 - Prob. 45PCh. 25 - 27.47 What product is formed from the [5,5]...Ch. 25 - 27.52 Draw the products of each reaction.
c....
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- Draw a molecular orbital picture for the LUMO of 1,3-Butadienearrow_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?arrow_forwardIs the molecular orbital diagram of 1,3-butadiene the same as cyclopenta-1,3-diene? If so how come? Doesn't the latter have 5 p orbitals or will it technically only have 4?arrow_forward
- Which one of the following represents the HOMO of 1,3-butadiene in the ground State?arrow_forwarda) Determine the molecular orbital energies and total energy of ethylene (C2H4). b) Determine the molecular orbital energies, total energy, and delocalization energy of [14]-annulene (shown in the figure).arrow_forward(c) Calculate the n-electron energy of the pi electrons a pentadiene radicalarrow_forward
- 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.arrow_forwardDraw the molecular orbital diagram for Ethene, 1,3 Butadiene and 1,3,5 Hexatrienes and indicate the HOMO and LUMO orbitals.arrow_forwardThe degree of unsaturation, or index of hydrogen deficiency, is the number of pi bonds plus rings in a molecule. Specify the degree of unsaturation (index of hydrogen deficiency) of the following formulas: (a) C9H12 (b) C,H40| (c) C,H,N2arrow_forward
- .For anion NO2-, (a) predict the stereochemistry. Justify your prediction with VSEPR theory and by formal charge; (b) indicate the hybridization appropriate to the stereochemistry; (c) describe the bond character of N-O for the resonance structure.arrow_forwardPrioritize these groups as 1,2,3 &4 with 1 being highest priority.arrow_forwardSquare planar molecules with formula AB2C2 and octahedral molecules with formulas AB4C2 and AB3C3 feature diastereoisomers. Recall that trigonal bipyramidal geometry features two distinct positions: axial and equatorial. Draw all diastereoisomers for trigonal bipyramidal molecules with formula (a) AB4C and (b) AB3C2. You must indicate the stereochemistry using full and dashed wedges and label all positions as either axial (ax) and equatorial (eq)..arrow_forward
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