Propose a 1, 2, or 3-step series of reactions to synthesize the target molecule from the indicated starting material. See the rubric for more expectations. ??? +CO,+H,O|
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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 CThe following figure shows the energy profile of a nucleophilic substitution reaction. Potential energy :ÖH H HII.C H C-1 H HO--C---I HH Reaction coordinate H -CH HO–CHITH H + 1 According to this, it is correct to affirm: O The activation energy (4G°) shows that it is thermodynamically favorable. O Represents a reaction that occurs in one step where a pentavalent chemical species is formed. O The intermediate has lower energy than any transition state. O The formation of the intermediate releases energy and is therefore thermodynamically favourable.b) Refer to the following equation to answer Q3b (i), (ii) and (iii). CH3 H,SO, Н—с—он C-CH3 ? + H2O Но- ČH3 (i) Determine the product of the above reaction. (ii) Name the above reaction. (iii) Propose the mechanism for the above reaction.
- 3. Show the mechanism for the acid catalyzed addition of H2O to the following ketone. OH H20 CH3 H* 4. The scheme below shows the reaction of a ketone, 2-propanone with methanol. OH :0 : || CH,-C-CH3 : ОН + H CH, c-CH3 CH;-C-CH3 N step 1 step 2 step 3 P CH,OH CH3 CH,OH step 4 + H OCH3 CH,-C-CH3 H - H,0 C-CH3 ÓCH, S CH; step 7 step 6 step 5 OCH3 i) Write the missing structures (N, O, Q and R) in the above reaction scheme. ii) Name the class of compounds P and S belong to? iii) This is an acid catalyzed reaction. What does this statement mean? iv) Draw the arrow diagram in step 6 to show how intermediate R is formed? Write the equation for this step ONLY. v) Steps 3 and 7 involve loss of a proton from the intermediate ions. Why is this step necessary?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:Provide the mechanism for the following reaction (1) PhMgBr (2 equiv) (2) H3O+ workup OH
- 3. For questions "A"- "C", complete the following reaction schemes (no mechanisms required). Show all reagents used in the order of application. th A) 6 B) ||| Ins HO HOTributyltin hydride (Bu3SnH) is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. Your job is todevelop a mechanism,In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.
- 3) Fill in the red box(es) with the missing reactant(s), reagent(s), product(s), solvent, and/or conditions and write a reasonable mechanism for the reaction. Not every box needs to be used and not every box necessarily corresponds to only a single species. If no reaction occurs OR no reagents exist to perform the reaction state, “NOT POSSIBLE” AND explain why. HO OH dil. H₂SO4H но. но HO Ethylene oxide is the starting material for the synthesis of 1,4-dioxepane. Draw curved arrows to show the movement ofelectrons in this step of the reaction mechanism. Arrow-pushing Instractions HO+ но H,ö: HO: :o: :o: I-MECHANISM ACTIVITY Base-Induced Ester Hydrolysis (Saponification) NOC XT Step 1: Nucleophilic addition of hydroxide ion to the ester carbonyl group Ahrs MPR R16 H3C. R Part A (1 of 2) Draw the curved arrows for Step 1 of this mechanism. Arrow-pushing Instructions CH3 H-O: ÖH OR' :Ö H-O: O: H H H H 1x xxx CH3 CH3 Step 1 H3C. CH3 за