Question 3. (10 Marks) Starting with 2,3,3-trimethylheptan-4-ol, plus any reagents seen this semester in CHEM3570, suggest a multi-step synthetic scheme that would generate a racemic mixture of 2,4-dimethylheptan-3-ol, in the final product box, in high yield (i.e. as the MAJOR product). OH 2,3,3-trimethylheptan-4-ol 2,4-dimethylheptan-3-ol (2 pairs of enantiomers) 3
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- ACHN a) Show the product in the provided small box. b) Draw a detailed step-by-step MECHANISM. In the mechanism show all relevant lone-pairs, charges and mechanistic arrows. Show all structures of formed intermediates, organic or inorganic. NHR OH 1. Dess-Martin-Periodinane (DMP), CH₂Cl2, room temp. 2. NEt3 product (precursor of Oseltamivir)Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. P H- :0: H H H H H H HH ΚΘ Select to Add Arrows CH3CH2OK, CH3CH2OH O :0: H. Select to Add ArrowsMechanism. Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. OH HO, H2SO4 (cat.) reflux
- Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistr CH₂CH3 CI Br + CN d. + CH3COOH a. acetone + -OCH3 e. DMF f. b. C. ||||| a ||||| Br H Br CH2CH2CH3 + CH3OH DMSO H CH3 CI Br + OCH₂CH3 + CH3CH₂OH(76 & A ... Switch account Q3: Identify reagents that can be used to accomplish each of the transformations shown below 9 7 2 3 4 Br 1 Your answer > 16← Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the curved arrows to draw the intermediates and product of the following reaction or mechanistic step(s). Include all lone pairs and charges as appropriate. Ignore inorganic byproducts. Problem 27 of 80 :0: :0: 0:0 CH2N2 H H H NEN N. Atoms, Bonds and Rings Draw or tap a new bo Q
- Which synthetic route(s) would complete the reaction shown? Br || ||| I and II O I and III ? HO OH + enantiomer Synthesis I: 1. NaCCCH3; 2. Na/NH3(I) ;3. OsO4; 4. NaHSO3, H₂O Synthesis II: 2. NaCCCH3; 2. H2, Lindlar's catalyst; 3. MCPBA; 4. aq. H₂SO4 Synthesis III: 1. NaCCCH3; 2. H₂, Pt; 3. MCPBA; 4. aq. H₂SO4In 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. CH₂Draw the organic product formed in the following reaction. H-N Job OEt OEt [1] NaOEt [2] CI [3] H₂O+, A NHAC HO "CH₂ edit structure ...
- 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) epoxideIdentify the major product of the reaction of an alkene shown below. ||| 1. Hg(OAc)2, H2O 2. NaBH4, NaOH ....... ОН || IV ОН о, ОНWhat is(are) the major final product(s) formed during the following sequence of reactions? 01 11 V 1.0₂ 2. (CH₂)₂S C₂H₂O 2 identical molecules ||| =PPhy < IV орна