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- PQ-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) H₂O8. 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)g) 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.
- 5) 1) MeO'Na* &r=&r MeOH 2) work-up (HCI, H₂O) 7) 8) NH OH 1) NaOH, H₂O 2) work-up (HCI, H₂O) HCI, H₂O heat 'H HO HO HCI, H₂O OH NH, CH How many stereoisomers are possible for this cyclic hemiacetal? OH5B. Are the pairs of structures shown below constitutional isomers, enantiomers, diastereomers, or the same? What is the degree of unsaturation for the compound in entry (e)? (a) (b) Me Me (c) F. H3C. ČH3 (e) (f) Et. ОН ОН Et Degree of unsaturation =(−)-Menthol is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol and has the R configuration at the hydroxyl-substituted carbon. (a) Draw the preferred conformation of (−)-menthol. (b) (+)-Isomenthol has the same constitution as (−)-menthol. The configurations at C-1 and C-2 of (+)-isomenthol are the opposite of the corresponding chirality centers of (−)-menthol. Write the preferred conformation of (+)-isomenthol.
- C П W Co X А) I В || I Ш E D) IV. "ОН none of these ОН 11 ОН "О H3O* OH OH + enantiomer ||| IV H 7 OF(a) (d) 5. Assign the R and S configurations for all stereogenic centers in the following compounds. BI H CH(CH₂)₂ KAMION WOH H₂C H CH₂ Br -H Br +H CH, (0) CH=CH₂ H+C₂0 -C=CCH₂ CH₂CH₂CH₂C1 CH₂CH₂CI H₂NH CH₂CH₂Cl CH₂CH₂CH₂OH H₂N CH₂CH₂OH CH₂Predict the expected major product(s) of the following reaction sequence. ی ہیں میں قبر ہیں H 1. t-BuOK, t-BuOH 2. O3, CH2Cl2, -78 °C 3. MezS H OH OH + enantiomer H
- 9. Which compound reacts with both NaBH and H/Pt to produce the same product? A) 1 4 2 B) II III CHO ||| D) None of these 10. Reduction of a carbonyl to produce a stereogenic center A) occurs with the formation of both diastereomers. B) occurs with the formation of both enantiomers. (C) occurs stereospecifically yielding a single isomeric product. D) none of these. MgBr 11. Which reagent would you use to produce (S)-1-phenylethanol from phenyl methyl ketone (acetophenone)? 12. A) S-CBS reagent B) R-CBS reagent C) NaBH +S-CBS reagent 4 D) NaBH + R-CBS reagent 4 An aldehyde can be produced by the reaction of the compound shown with which reagent? A) B) || D IV OCH3 I) H₁/Pt III) LiAlH4 II) NaBH4 IV) DIBAL-H 13. LiAlH reacts with which of the following? 4 A) | H .0 CI 0 EtO. 0 B) C) III D) All of these I II III5) Draw the following molecules from their given names, determine if they are chiral or meso. a) (1R,25,3R,4S)-1,2-dichloro-3,4-dimethylcyclobutane b) (2R,3S)-2,3-dimethylcyclohexanone c) (1R,3S)-1,3-difluorocyclopentane d) (1S,3S)-1,3-difluorocyclopentane8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomers