Mechanism 1. Provide the complete mechanism for the reaction below and predict the product. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. CI 1. NaBH(OCH3)3 (1 eq), CH₂OH 2. HCI, H₂O
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- The 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 C2. Provide the mechanism for the reaction illustrated below. Show the relevant intermediate/transition state. Br N2OHConsider 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,C
- Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:Mechanism 1. Provide the complete mechanism for the reaction below and predict the product. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. зов 1. NaBH(OCH3)3 (1 eq), CH3OH 2. HCI, H₂O Mechanism 2. Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. ই 1. NaBH4, CH3OH 2. HCI, H₂O میدOH OH ∞∞ BF3 Et₂O This reaction takes place via a pinacol rerrangement. Please, draw curved arrows to show the movement of electrons in this SPECIFIC step of the reaction mechanism. +BF3 HO: :OH OH (BF3OH)
- Predict the intermediates and final product. Provide a rational mechanism.7A Complete the reactions of the course below by briefly explaining. OH A CI B NH₂ Note: Each conversion does not necessarily correspond to a stage, more stages may be required.Consider the reaction scheme below. (i) H3COCHN CO₂Et A H₂N OH EtO OEt B C6H₁1 NO2 base Ha Identify the reagent(s) and conditions A and the intermediate B in this reaction scheme.
- A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. Example: OH bond breaks here synthesis Br + retrosynthesis NEC Na -NaBr Synthons C-C bond formation synthetic equivalents Br D=00 CN OH || ⒸC=N H₂O, H+ hydrolysis do not exist exist functional group transformation Common synthons: C1 synthons: carbon dioxide, carbon monoxide, cyanide, formaldehyde C2 synthons: acetylene, acetaldehyde C₂H4OH synthon: ethylene oxide OH Carbocation synthons: alkyl halides, carbonyl C Carbanion synthons: Grignard reagents, organolithiums, malonic ester/acetoacetic ester, terminal alkyne Use the synthons listed above, propose how you would synthesis the following molecules:Use curved arrow formalism to draw the mechanism of the reaction shown below. Include intermediates and their relevant resonance forms. Be sure to account for all the products. Br CH3OH OCH3 + Joc 1w OCH 3In each reaction box, place the best reagent and conditions from the list provided. 1) Br 2) 3) 4) DEET (the active ingredient in over the counter insect repellant) 5) Answer Bank Mg, Et,0 HN(CH, CH, ), (1 equiv.) H,O* CH,COOH CH,CH,NH, CH,CH, Br NH(CH,CH,),(2 cquiv.) НСООСH, H,CO НСООН CH, CH, OH NaCN NaNH, Br,, FeBr, SOCI, CO,