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- It is often helpful to have more than one way to make a given molecule, as you may not know ahead of time which strategy will be more successful.... 4-Hexyne-2-ol can be made from propene in two different ways – one by way of a bromohydrin, using a protecting group strategy, and another by using an epoxide (which does not need a protecting group strategy). (a) First, give the synthesis which goes through the bromohydrin and uses a protecting group. OH (b) Now, modify the synthesis (you may start with propene, or any other molecule you already made in part (a)) to accomplish the synthesis of 4-hexyne-2-ol using an epoxide.below. Draw the structure of each intermediate for each reaction. You can use anything with a Provide a reasonable synthesis to produce the compound shown maximum of one carbon atom or propene as your only source of carbon for the synthesis of the compound below. You may use other reagents, solvents, acids and bases (all of which cannot be a source of carbon) for the synthesis of the compound below.1. (cont.) CH3 Cl- -CF3 CH;NH2 (i) H ОН ČH,CH3 CH, 1. PBr,/pyridine (j) ОН 2. NaOH/DMSO 2. Using the given starting material and any necessary reagents indicate how the following syntheses can be carried out. ОН CH;CH,CHCH3 CH,CH,CH,COH OH CH;CH,CHCH3 CH;CH,C=CH .OTS OCH3 CH3 CH3 ОН 3. Propose a mechanism that accounts for the formation of the product shown during the following observed reaction. Be sure to show all intermediates. ОН H+
- In the problem-solving feature below, methylcyclohexanone was seen to react at its unsubstituted c carbon. Try to write a mechanism for the same reaction at the methylsubstituted carbon atom, and explain why this regiochemistry is not observed. CH₂CH₂0- H H O CH3 Н. O CH, H. :0: + CH₂CH₂OH Draw all missing reactants, reagents, Intermediates, and/or products inside the appropriate boxes by choosing buttons from the Tools (for bonds and charges), Atoms, and Templates toolbars. CH₂What alkene is needed to synthesize the following 1,2-diol using the given reagents? Be sure to answer all parts. CH3CH₂CH2 [1] OsO4 followed by NaHSO3 in H₂O: [2] CH3CO3H followed by "OH in H₂O: H OH OH CH₂CH₂CH3 draw structure... draw structure ...Be sure to answer all parts. Synthesize the following compound from cyclohexanol, ethanol, and any other needed reagents. он Part 1 out of 2 Preparation of organometallic reagent: B CH3CH2OH CH3CH2MGB. draw structure... Draw the intermediate product above and select the correct reagent for A. NaBr O MgBr2 Br2 HBr Select the correct reagent for B. O Mgo O Mgl, O Mg O MgBr2 Next part
- Draw the structure(s) of the major organic product(s) of the following reaction. t at 1. lithium diisopropylamide / hexane t 2. 1 eq. CH2=CH-CH2CI ot • You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr), derived from N(i- ot t Pr)2". If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ot t ot4) Starting from benzene and propionic anhydride as the only sources of carbon in the final product, propose a multi-step synthesis for the indicated 1,3,5-trisubstituted benzene only using reactions discussed in class and in the text book. Be sure to indicate ALL necessary reagents and isolated intermediate products. Me HN steps and Ме Me only sources of carbon in final product MeComplete the following syntheses by providing the reagents and conditions at the reaction arrows. (Multiple steps: 1) do this.... 2) then do this, etc. ) 6. он 1) MgBr Br 2) Br он Br Br 1) p- + OH 2)
- How is the mechanism for oxymercuration/demercuration reactions of alkenes understood? How are the (Markovnikov) products predicted and what reagents would you need to use to incorporate this reaction into a multistep synthesis strategy. Finally, what makes this a potentially more useful way to synthesize alcohols from alkenes than simple acid hydration?1. Consider the following reaction. The reagent for the elimination/substitution reaction contains the following anions: Br and CN". он several products a) Define the reaction conditions for the reaction above. Explain in detail. b) Which of the anions will take part in the reaction? Explain. c) Provide the structures of all major products. Specify the stereochemistry where applicable and state the reaction type leading to each product. d) Provide a reaction mechanism for the formation of the products listed in c.Be sure to answer all parts. Devise a synthesis of the product compound from the indicated starting material and the given reagents. CH3CH;CH;CH;OH CH,CH, CH3 POCIy CH;CH½CH, CH,01H pyridine draw structfure mCPBA draw structure... II) LIAIH, CrOy H2 SO4, H20 CH,CH, CH3 draw structure ... %23