Write out all the steps in the mechanism of this electrophilic aromatic substitution reaction. Include all resonance contributors. Benzene Cl₂ FeCl3 chlorobenzene
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- 9) Suppose I want to perform a simple substitution reaction, replacing the OH with a Cl in the following compound. Which of the following reagents works best? Explain (and that means explain why the wrong answers are wrong as well as why the right answer is right). Option A: Addition of HBr Option B: Addition of SOC12/pyridine Option C: Addition of SOCl2 only OH ? J1Possible alternative brominations include: Veratrole (1,2-dimethoxybenzene) to 1,2-dibromo-4,5-dimethoxybenzene; 4-Methylacetanilide to 2-bromo-4-methylacetanilide; 2-Methylacetanilide (made in experiment S.1) to 4-bromo-2-methylacetanilide; Vanillin to 5-bromovanillin; Acetanilide to 4-bromoacetanilide; a. b. C. d. e. EXPERIMENT S4: BROMINATION OF AROMATIC COMPOUNDS Certain other acetanilides made in experiment S.1 may also be used as precursors in this experiment. Estimated time: 1 afternoon Associated learning goals: Section 6, LG 6.6; Section 7, LG 7.2 and 7.4 Pre-lab report: complete the standard report form, and answer the following questions. In this experiment, molecular bromine (Br2) is generated from the redox reaction of potassium bromate with hydrobromic acid. Write a balanced equation for this process. Briefly outline the mechanism by which Br2 brominates your aromatic compound. Why do the bromine atoms end up at the positions indicated rather than anywhere else in the…Review topics] [References) 1. CI NaOH NH2 NaCI H20 2. OH NAHCO3 12 H20 CO2 Nal a = Proton transfer d = Electrophilic addition g = SN1 Nucleophilic substitution b = Lewis acid/base c = Radical chain substitution e = El Elimination h = SN2 Nucleophilic substitution f= E2 Elimination Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. 2. Retry Entire Group 9 more group attempts remaining nswer
- c) For the following substituted benzenes, please rank their relative rates of reactivity in an EAS substitution reaction with HNO3/H2SO4, where 1 = fastest, or most reactive, and 6 = slowest, or least reactive. OMe Br Br NO2 `NO2Q2Show why the OH functional group, of phenol below, is ortho directing using curly arrows to show the formation of each of the four resonance structures A, B, C and D. Draw all the resonance structures A through D and explain why one resonance structure is more favourable than the other three in directing the electrophile (E*) ortho to the OH functional group.3. Nucleophilic aromatic substitution (NAS) reactions have the opposite trend in terms of reaction rate when compared with SN2 reaction rates. This is to say that aromatic fluorides undergo substitution the fastest under NAS conditions but the slowest under SN2 conditions. Using your knowledge of the mechanisms of these reactions, explain why this is the case. (Hint: It is important to consider the rate-determining step of each mechanism). NuO Nu Rate of reaction follows the following trend: F> CI > Br>1 NuO Nu Rate of reaction follows the following trend: I> Br > CI >F
- This reaction does not follow the expected theory. Given what you know about substitution/elimination, what is the expected mechanism this reaction should follow? Suggest why that is not what happens and give the actual product of the reaction. Br ткон s9. On each of the structures shown below mark with an arrow where electrophilic aromatic substitution would take place. CN SO3H OH NO₂Draw the sigma complex for the formation of the bromonium electrophile with proper resonance forms for the meta bromination of toluene and for the para bromination of toluene. Which resonance structure places the (+) next to the methyl group? Will either one (i.e. para and meta sigma complex) yield a fourth resonance structure? Given that alkyl groups such as CH3 are electron rich (i.e. no attached electronegative atoms), which sigma complex in part (A) would be more stable?
- Reaction of 2-methyl-2-butene (above) with HBr might, in principle, lead to a mixture of two alkyl bromide addition products. Draw these two alkyl bromides.3. Propose a reasonable mechanism for the reaction. Remember to: 1) Draw out the Lewis structure 2) Use arrows to indicate electron flow, clearly identifying the bond making and bond breaking steps. 3) Propose reasonable intermediates for the reaction conditions. Hint: One of the intermediates is a "dienol" which leads to an interesting tautomerization. For practice include the tautomerization in your mechanism. (Ph= phenyl = C6Hs) Ph 4. a. b. C. d. OH + H₂O H,CO. f. Ph cat. H₂SO4 For the reactions below, choose an appropriate reagent for the transformation. HO HICO. Reagent OH S HO Reagent + CO₂ Reagent Reagent Reagent H Ph Reagent -PhReaction of propene (above) with HBr might, in principle, lead to a mixture of two alkyl bromide addition products. Name these two alkyl bromides.