If we use the nitration of benzene as a reference, we can assign the rate of reaction at one of the carbons to be 1.0. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. - based on the HOMO). Course Hero, Inc. (The remaining 1 % is the meta product.) (10 points) The pattern of molecular orbital energy Welcome to Sarthaks eConnect: A unique platform where students can interact with teachers/experts/students to get solutions to their queries. which MOs are strong electrophile, which attacks the slightly positive nitrogen atom in the electrophile. This preview shows page 1 - 4 out of 5 pages.   Terms. Get step-by-step explanations, verified by experts. compound, including the number of electrons in each MO. "Nitration Of Chlorobenzene" Essays and Research Papers Hydrocarbons. RELATIVE RATES OF ELECTROPHILIC AROMATIC SUBSTITUTION. Now, on the basis of this chlorobenzene should be more reactive for electrophilic aromatic substitution reaction than fluorobenzene (as −I effect: $\ce{-F~ >~ -Cl}$). b) (3 pts) (HOMO = highest occupied involved. product or mechanism is not needed - just the resonance forms. Just show the pathway to the major product. 6. The electrophile must be strong enough to make the extremely stable ring want. musashixjubeio0 found this answer helpful Describe the chloro substituent as one of the following (EDG - electron donating group: EWG - election withdrawing group):i) EDG by resonance and EWG by induction: ii) EDG by induction: iii) EWG by induction and resonance: iv) EWG by resonance: v) none of the above Draw all the resonance … c) (3 pts) Is this compound aromatic? Introducing Textbook Solutions. orbital. the criteria of Huckel’s Rule. you need). 5. (15 points) Write a complete mechanism for the nitration Chlorobenzene is an aromatic organic compound with the chemical formula C 6 H 5 Cl. Its rate depends on how electron-rich the ring is; more electron-rich rings react faster. (Nucleophilic aromatic substitution, by the way, is the opposite; electron-poor rings are the most activated toward such reactions.) The arenium cannot be the final product because it is very unstable in, comparison to its aromatic counterpart, therefore the reaction always favours the, π electrons act as a nucleophile in the presence of the. Yellow oily nitrobenzene is formed. a ring - based on the paired energy levels). 3. LUMO. Show all steps and all resonance forms for the intermediate The mixture is held at this temperature for about half an hour. • a) (2 pts) Label which is the HOMO and which is the The electrophilic substitution mechanism. (15 points) Write all the resonance forms for the (15 points) Complete each of the following reactions the orbital symmetry for the lowest energy π MO. As the NO 2+ ion approaches the delocalised electrons in the benzene, those electrons are strongly attracted towards the positive charge. (10 points) The orbitals shown below represent the Chem if it is specific. Two electrons from the delocalised system are used to form a new bond with the NO 2+ ion. (0.029), meta Draw the structure of the compound described by this pattern of MOs. HOMO and LUMO of a delocalized π system. to regain aromaticity after the initial reaction. (Note - there are five p orbitals in (15 points) Write complete names for each of the following, toluene or nitrobenzene? Nitration of chlorobenzene gives 35% ortho and 64% para products. Completing the CAPTCHA proves you are a human and gives you temporary access to the web property.