Interpretation:
The relative energy levels of the five π molecular orbitals of the cyclopenta dienyl system are similar to those in benzene. There is a single lowest energy MO, above which the orbitals come in degenerate pairs. A similar MO diagram is to be drawn for cyclopentadiene cation, radical and anion. How these mplecular orbitals are filled in all the three species is to be shown.
Concept introduction:
The numberof molecular orbitals formed is equal to the number of orbitals overlapping. The available orbitals are filled by the electrons in the increasing order of their energies. Each moleclar orbital can accommodate two electrons with opposite spin. Electrons occupy the orbitals individually first before they get paired in the same orbital.
The cyclopentadienyl cation has four electrons to be filled in molecular orbitals.
The cyclopentadienyl radical has five electrons to be filled in molecular orbitals.
The cyclopentadienyl anion has six electrons to be filled in molecular orbitals.
To draw:
The relative energy levels of the five π molecular orbitals of the cyclopenta dienyl cation, radical and anion.
To show:
How the five π molecular orbitals are filled in cyclopentadienyl cation, radical and anion.
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Organic Chemistry
- Write an equation for the reaction of CH3 C(=O)OCH₂ CH3 with BF3, a Lewis acid, and show by the use of curved arrows how the reaction occurs. Show all hydrogen atoms that are not attached to a carbon atom. Apply formal charges where appropriate. • Assign lone pairs and radical electrons where appropriate. ● Use the "starting points" menu to revert to the original molecule(s) shown. • Draw the appropriate electron-flow arrows. Omit+ signs between structures. ● CH3 c=0 :0: d HC ។ CH3 O n ChemDoodle Previous Nextarrow_forwardSelect all statements that are true regarding tertiary radicals - Tertiary radicals are more stable than primary radicals due to increased hyperconjugation from attached alkyl groups. - The CH bond that leads to a tertiary radical via homolysis has a higher bond dissociation energy that the CH bond leading to a primary radical - Tertiary radical hybridization geometry is best described as sp2 hybridization rather than sp3 hybridization - Radical chlorination reactions are more regioselective than radical bromination reactions when a tertiary radical can form.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH,CHCH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.arrow_forward
- Consider the following structures: CH, CH3 H;C, „NH3 H,C, CH H3C, Br H3C. CH CH3 CH3 CH3 JECE CEEJ JEEC СЕЈЕ ЕСЕ Which is a resonance contributor? ECJE Which has a net formal charge of +1? JECE Which has only one type of hydrogen? ECJE Which will form the most stable free radical? JEEC Which is an electrophile? JEECarrow_forward||| = O PRINCIPLES OF ORGANIC CHEMISTRY Identifying rigid parts of an acyclic organic molecule In the actual molecule of which this is a Lewis structure, which of the labeled distances can change? H marked O G: F H B C H A N. unmarked G с N O H 0,0.... List all the distances that can change. For example, suppose all the distances were measured at a certain time, and again 0.1s later. If distance A might be 50% bigger or smaller the second time, but all the other distances are certain to be the same, you should write "A". If A and B might be different the second time, but no other distances, you would write "A, B". And so on. Note for advanced students: you can assume the molecule is dissolved in an appropriate solvent at room temperature. X 0/5 You can click the "unmarked" tab to see the molecule without any of the distances marked. S Jacari V 18 CO olo Ararrow_forwardIdentifying organic functional groups Name the family to which each organiC compound belongs. The first answer has been filled in for you. compound family ester CH,– CH,– -0–C – CH, CH; CH, — о — с —Н CH, NH, – C=O CH, Check Explanation O2021 McGraw Hill LLC. All Rights Reserved. Terms ||arrow_forward
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- 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 pmarrow_forwardTestosterone is an anabolic steroid. The structure of testosterone is shown below. What is the idealised bond angle at the indicated atom (i) ? Hint: atom (iv) has been completed for you as an example. (iv) bond angle: 109.5°, geometry of the electron pairs: tetrahedral, shape of the bonds: tetrahedral iii |||I H H ….………|||I H ii ivarrow_forwardThe compound below is treated with chlorine in the presence of light. CH3CH2CH2CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning