Show the formation of carbocations for each of the following steps: CF3 Н,о Нeat .CI AICI, In the following, carbocation undergo rearrangement through hydride shift and alkyl shift. Explain by drawing the steps: Hydride shift Alkyl shift
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- Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.Explain the Carbocation Rearrangements ?Which of the following is NOT a rearrangement reaction? CH, CH, H,C CH, + CH3 H,C CH3 CH, CH, CH, CH, CH, H,C H,C + CH CH CH, CH, H,C H.
- Consider the following overall reaction, which will be discussed in Chapter 20. H,C-CEN NH3 HOO H,C Below is a proposed mechanism for this reaction. Use the rules we learned in this chapter to evaluate whether each step in the proposed mechanism is reasonable. For each step that is not reasonable, explain why. :ÖH () H,C-CEN: H3C OH OH (i) + H,C H3C OH OH (ii) H,C H,C OH (iv) + H,O: H,C H,C OH (v) H3C H3C OH H. (vi) :NH, NH. H,C H,CThe accepted mechanism for a rearrangement reaction is shown below. "Q Ph (1) (ii) Ph Ph HO™ fast Ph Ph HO O™ slow Ph aufae .Ar² LOH HO™ fast Draw a curly arrow mechanism for this transformation. Sketch an energy profile for this reaction, showing approximate relative energies for the reactants, intermediates, transition states, and products. HQ Ph (iii) When DO™ was used as the reagent, the rate of product formation was same as for HO™. Explain why this result shows that the third step is fast and cannot be rate-determining. Ph (iv) Write the predicted rate equation for this mechanism, and show how it was derived. (v) The starting diketone may have two different aryl groups, as shown below. Propose a ¹³℃ labelling experiment that would allow you to distinguish which of the two aryl groups had migrated in this situation. OH AR²0- Ar¹ C CFour carbocations are shown, which can possibly rearrange via hydride shift to a more stable carbocation. H H „CH2 H3C CH3 H3C A D Select the carbocation(s) that will rearrange via hydride shift. B A D
- Which is true of a free energy diagram for an SN1 eaction? It shows one transition state. It always shows that the reaction is net exothermic. It never shows intermediates. It always shows that the reaction is net endothermic. It always includes multiple energy barriers.The electrophilic addition of Br, to several alkenes was examined. Explain why the relative reaction rates are as follows: H. H H CH3 H CH3 H CH3 H3C CH3 < C H H H H3C H H3C CH3 H3C CH3 Increasing reaction rate with Br26. The product(s) of the following reaction dd blow di CH2-CH2 excess HBr is/are: CH2 CH2 heat Od Al () (A od Ocf D (CHPPCOK (CHPCON G)D CH;CH2OCH,CH3 HO CH;CH,CH,CH,OH and CH;CH,CH2CH,Br II H t mol boumol toubong soinm od o CH2-CHBR HO CH2 CH2 BrCH-CH,CH-Cн,ОН and BrCH,CH,CH-CH,Br CityCHCH COM III IV A) I B) П O II D) IV E) None of these HO CH CH'OH
- Complete the reaction with a major product: Ph. D-C-CH2CHO PhCH₂CHDCH₂CH=CHCH₂ CH₂CH=CHCHDCH₂CH₂Ph A OA hv Additional requirement: sketch the reaction scheme on paper and use the proper arrow sign to indicate electron movement in the reaction for either bond formation or breaking. Use the results you get for answers here. B OC -CH₂CH₂2. Provide the mechanism for the reaction illustrated below. Show the relevant intermediate/transition state. Br N2OH4. What are the products obtained from the following elimination reaction? Indicate the major product. CH;CH2CCH3 H2O CI 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH3 Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.