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Concept explainers
Interpretation:
The molecular orbital diagram for ground state of cyclopentadiene is to be completed; appropriate lobes are to be shaded to indicate the phase signs. HOMO and LUMO orbitals are to be labeled. Appropriate number of electrons, using straight single-barbed arrows in each level, is to be represented.
Concept introduction:
舧 Molecular orbital diagrams are used to explain the linear combination of atomic orbitals.
舧 HOMO and LUMO are types of molecular orbitals and are abbreviations for highest occupied molecular orbital and lowest unoccupied molecular orbital, respectively.
舧 Each lobe is a representation of p-orbital and each lobe has two poles, that is, shaded and non-shaded regions.
舧 The orbitals are aligned in such a way that each double bond in cyclopentadiene has the same orbitals.
舧 The lowest energy position is where all orbitals are shaded on top and clear on bottom.
舧 The second energy level has one orbital overlap.
舧 Third energy level has no orbital overlap but the two orbitals in the same alignment create similar signs through-space conjugation.
舧 Fourth energy level has no orbital overlaps or no sign changes and hence, it is the most unstable.
舧 There are two pi-bonds in cyclopentadiene, meaning 4 pi-electrons present in the system.
舧 The pi-electrons fill the lowest energy level.
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Chapter 13 Solutions
Organic Chemistry
- 5. 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_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_forward5) Use the template below to complete a full schematic picture of the molecular orbitals of the Pentadienyl ANION by only showing the interacting p atomic orbitals. Indicate the number of nodes in each, as well as the HOMO and LUMO. Energy 88888 electrons nodesarrow_forward
- (a) Use the polygon rule to draw an energy diagram for the MOs of a planar cyclooctatetraenyl system. (b) Fill in the eight pi electrons for cyclooctatetraene. Is this electronic configuration aromatic or antiaromatic? Could the cyclooctatetraene system be aromatic if it gained or lost electrons? (c) Draw pictorial representations for the three bonding MOs and the two nonbonding MOs of cyclooctatetraene. The antibonding MOs are difficult to draw, except for the all-antibonding MO.arrow_forwardCompound C show below is the starting material used in a chemical reaction. a) Name the two functional groups present in compound C. b) Assign the stereocentre present in compound C, using Cahn-Ingold-Prelog rules, clearly indicating priorities. c) Label the hybridisation of all non-hydrogen atoms found in compound C. d) With the use of an appropriate diagram described the bonding found in the C=O bond. Include details of the orbitals involved, the types of bonds formed and the location of any lone pairs of electrons.arrow_forward5) Draw an MO diagram for the square planar molecule Sn("Bu)a. Draw each SALC that you generate and each orbital within the final MO diagram. Label your orbitals as o", n, o' etc. and include the appropriate # of electrons. Compare your MO diagram to the Ta version done in class and provide an explanation for which geometry you think is would be more stable. Hint: you can use the d-orbitals as a template though they are not available for bonding.arrow_forward
- (a) Draw an energy diagram for the cyclopropenyl MOs. (The polygon rule is helpful.) Label each MO as bonding, nonbonding, or antibonding, and add the nonbonding line. Notice that it goes through the approximate average of the MOs.(b) Add electrons to your energy diagram to show the configuration of the cyclopropenyl cation and the cyclopropenyl anion. Which is aromatic and which is antiaromatic?arrow_forward1. The energy of a photon is. proportional to its wavelength and proportional to its frequency. (directly or indirectly) 2. Which of the following has a lower characteristic stretching frequency, the C O bond or the C-O bond? Explain briefly. C=0 3. Ethyne HCECH does not show IR absorption in the region 2000-2500 em-! because. 4. Which statement best explains why a carbonyl absorbs infrared radiation at a higher frequency than an alkene absorption?arrow_forwardPlease absolute configuration of these compounds .arrow_forward
- Two constitutionally distinct products are generated from the reaction of HBr with 1,3-butadiene. a) What type of reaction is indicated here? Utilize arrow pushing to indicate the mechanistic steps for this reaction. b) Draw hybridization orbitals on this molecule around the carbons for proper 3D geometry. Could you recognize any special situation occurring here? + H-Brarrow_forwardPlease answer this NEATLY, COMPLETELY, and CORRECTLY for an UPVOTE. Long and detailed explanations are not needed. Keep it short, brief, and direct because I only need the answers as soon as possible. Given the three Newman projections drawn below, rank them in order of increasing stability.arrow_forwardAnswer the questions for 1,3,5-hexatriene, the conjugated triene containing six carbons. Select all that apply. 000000 Q00000 000000 Q00000 000000 000000 How many a molecular orbitals are there? O 3 Energy of the p atomic orbitals 器器 A2 00000 000000 a molecular orbitals Which a molecular orbitals are symmetric? Which t molecular orbitals are antisymmetric? T2 | T2 O T1 O O O O O O O O O Energy O O O O O Oarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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