choice. b. (4 pts) Assign configurations (R or S) to all stereocenters in the products. vs. (1 pt) Unlike NaBH4, reductions carried out with DIBAL require quantities equimolarof DIBAL and substrate. Can you explain this difference? MAJOR MINOR را الان ομ H TOH
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choice. b. (4 pts) Assign configurations ( R or S ) to all stereocenters in the products. vs. (1 pt) Unlike NaBH4, reductions carried out with DIBAL require quantities equimolarof DIBAL and substrate. Can you explain this difference? MinOR Help wirh part B please, please show working out
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- b. VS: Assign configurations (R or S) to all stereocenters in the products. Unlike NaBH4, reductions carried out with DIBAL require quantities equimolarof DIBAL and substrate. Can you explain this difference? 4 ομ H TOH8. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) H3C c) CH3 Br H. CH3 Br Br CH3 H. CI Holl H Cill Cl- CH3 Br H. CI CH3 HO. H. H3C Cl H3C- H- H. CH3 Cl a) b) c) 9. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) c) CH2CH3 NH2 HO CH3 H3C. CH3 Cl HO H;C CH2CH3 F. F H;C. CI H H,N -CH3 CH3 NH2 H3C Br H2N C1 H3C CH3 CH3 H;CH,C- Cl F H. H Br CH,CH3 CH3 a) b) c)S) Draw the expected major product (except when I explicitly ask for a minor product) in each box NaOCI CH;CO,H : CH,CN : H20 1) `MgBr OH 2) H20 C10H180 C12H240 C12H240 major stereoisomer minor stereoisomer base C13H9F203 "Fiflunisal" NSAID Drug produced by Merck in 1971 NC. CN heat C10H12N2 enant #1 C1OH12N2 enant #2 show "relative stereochemistry" of the methyl groups in the product for full credit. Two enantiomers are produced, draw one in one box, the other in the other box.
- Predict the major product of this series of reactions. The squiggly bond simply indicates the stereochemistry is unknown, i.e., wedge or dash. HBr compound I 1. NaH 2. compoundI 3. H2, Lindlar 4. Br2, H20 OH Br А. Br C. OH OH Br Br В. D. OH A.]>90% e.e. TSOH (cat.), CH,Cl2 then workup racemic но mostly one diastereomer ]5:1 diastereomer mix product after these transformations >90% e.e. 2) a) NANH2, THF, -20 °C b) OHC-CH,CH3 c) workup ]racemic mostly one diastereomer 3) NaH, MegSi-CI, then workup ] 5:1 diastereomer mix product after these transformations5. Given the following structure: (a) Draw all the stereoisomers; CH2 OH (b) Identify all of the enantiomeric and diastereomeric pairs; (c) Assign R or S configuration at each asymmetric carbon for each structure. Justify your assignments for the original structure (above).
- 6. a) For each of the following pairs of molecules, identify the stereochemical relationship. Are they enantiomers, diastereomers, constitutional isomers, or the same molecule. CH3 н— сно i) ii) CHO H3C-OH НО HO ОН CI H CI iii) iv) Br H H H CI H. Br CI CI CI b) Explain why carbocation A is formed in step 2, rather than carbocation B (formed by the mechanism shown below). A BPQ-17. How is this reaction characterized? (A) only regioselective (B) both regioselective and stereospecific (C) only stereospecific (D) neither regioselective nor stereospecific ~ 1) KMnO4. OH, 0°C 2) H₂Og) Reaction 1g pts] For 2-chloro-3-fluorocyclohexane, draw all possible stereoisomers, and identify their stereochemical relationships using the labels we used in class (E = enantiomers; D=Diastereomers; I = identical.) Make sure to label each chiral carbon in each compound with the correct R/S designation.
- C. IDENTIFYING STEREOISOMERS: Label each pair of molecules below as enantiomers, diastereomers or identical CO₂H HO HC но-- н H -.Н CH3 OH CH₂OH HO™ H₂OC H₂C Н-- HO Н CH3 OHH CH₂OH HOC-... HOCH₂. H OH H OH HO H CHO COzH ОНС но с HO H COzH Н ОН НО Н CH₂OHComplete the following reactions. Show the stereochemistry where applicable. DMF iBT + H₂ CN CHS сиз си-ей антена сцена в E2 Br +cla/mo perotide : No OH > H₂ Croutz MgBr 애 + HBr + pac po ой + pels ❤ CH-CH- снесия стану NBS +H20 heat H NANH2 HH₂(1) H₂ 504 > Cl Си-Ен= CH2-CH-он Кмпой (G) YL5. Give the stereochemical relationship between each pair of isomers. Examples are same compound (meso), constitutional isomers, enantiomers, and diastereomers. H3C CH3 HO OH lll a. Но OH H Br CH3 b. C/ H3C CI H. ICH3 CH3 с. CH3 H. CH3 d. Но. H3C OH CH2OH Ho CH2OH Br e. Br H3C f. H CH3 H3C CH3