3) Synthesis Planning: For the following synthesis problems: a) Show the retrosynthetic disconnection that is necessary to accomplish the transformation, b) Show the disconnected fragments ("Synthons"), and c) Show the reagents and steps needed to accomplish the reaction. Show intermediates when necessary. (Hint: part a can be done in 1 step!) H3C O nPr nPr & OH com H3C
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- 2. The reaction shown below was performed as part of a research program funded by the National Institute of Health (NIH) to develop therapeutic agents for the treatment of cocaine addiction. ● HT ● H 1₂ NaHCO3 ↑ sodium bicarbonate = mild base H AFH O HO O Using what you have learned in Chapter 8 about the addition reactions of halogens with alkenes draw a complete arrow-pushing mechanism for this process to include the following: Show all arrows for each mechanistic step, to illustrate correct electron flow Structures of all reaction intermediates formed in the mechanism must be shown correctly, including the key cyclic iodonium ion intermediate Underline the iodonium ion intermediate that is formed in the reaction Stereochemistry of reaction intermediates consistent with the product stereochemistry shown Formal charges where applicableBr ند -بد F Br Hint Ph 1 1) R2BH 2) H2O2, H2O D H2O, H2SO4, H2SO4 The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A OH B 1) 03 2) 20 Ph E 3 OH H2, Lindlar's catalyst C 1) xs NaNH2 2) H3O+ workup F H2, PdOH 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)
- Dtermine the reagents that can accomplish the rxn CH2OH (1) Reagent ? (2) Reagent ? C9H1202 (4) Reagent ? (3) H+ a. (1) SOC12 (2) 1-propanol; (4) PCC/pyridine b. (1) NaH, (2) acetone, (4) NABH4 c. (1) NaH, (2) epoxide (4) PCC/pyridine d. (1) Jones reagent, (2) NaH, (4) epoxide4. Use the reactant below to perform two separate reactions. Give the mechanism(s) and product(s) for each reaction. Show stereochemistry and be clear in your work. Use chair form. KOEt, EtOH t-Bu |||| H3O+Provide the reagents needed to perform the (a)-(g) conversions. Some reactions may require more than one step, so you may need to provide more than one reagent. Он CH3 CH3 b) HO c) d) f) el но OCH3
- c) Complete the following reaction scheme below with reagents N and O, and structures P and Q. OH N HO НО KMNO4 P SO3 / H,SO4 Q5) Determine reaction conditions needed for a multiple step synthesis to transform the starting material into the product. Show the product after each step (but you do not need to show reactive intermediates or mechanisms). OH3. 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?
- CS41 10.) Chapter 7: E2 SNI + EI SN1+ E1 Mechanisms. Using correct mechanistic arrows, provide the step-by-step mechanism that demonstrates how the following reactions proceed to afford both substitution and elimination products via SN1 and E1. You do not need to show stereochemistry while providing the mechanism, but show correct stereochemistry in the final product(s). If there is more than one product feel free to write +E or +D as appropriate (or just write your products). C341 Br CH3NH2 CH3CH2OH CH₂OH Br CH3CH₂OH A Page 5 of Chapter 7: E2 SNI + E1Which of the following is the best method to carry out the following transformation? OH (a) H₂SO4, H₂O (b) 1. BH3 2. H₂O2, OH (c) 1. Hg(OAc)₂2 H₂O 2. NaBH. (d) 1. HBr 2. H₂OIdentify the major product of the following reaction sequence. 1) [H*], H₂NNH2, (-H₂O) 2) KOH/H₂O, heat HO₂C HO₂C HO CO,H OH OH There is no reaction under these conditions or the correct product is not listed here.