Q7. Using the Cahn-Ingold-Prelog rule, assign the absolute stereochemistry to each stereggenic centre in compounds a-d, and determine whether they are chiral or not. a) b) OH CI OH H3C H3C CH3 NH2 CH3
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- Q7. Using the CabolagaldRKalog rule, assign the absolute stereochemistry to each stereogenic centre in compounds a-d, and determine whether they are chiral or not. a) b) OH OH H3C CH3 H3C CH3 NH2 c) d) OH H -0 H- H3C CH3 н он OH ОНQ8. Draw the two possible chair-like conformations of compound 1. Using the Çabo LAgld erelog priority rules, assign the absolute stereochemistry to each stareogenic centre contained in compound 1. NH2 'F 1Q7. Using the Cahn-Ingold-Prelog rule, assign the absolute stereochemistry to each stereogenic centre in compounds a-d, and determine whether they are chiral or not. а) b) ОН CI OH H3C CH3 H3C CH3 NH2 c) d) OH H O- H- Н он H3C* 'CH3 OH ОН
- Q8. Draw the two possible chair-like conformations of compound 1. 2 Using the Cahn Ingold Prelog priority rules, assign the absolute stereochemistry to each stereogenic centre contained in compound 1. NH2 14. Draw all possible stereoisomers of the following compounds. Assign the appropriate absolute (R/S) or geometric (E/Z) configuration to each of the stereoisomers (or double bonds) and label pairs enantiomers, diastereomers and meso compounds. (a) CH3CHBRCHOHCH3 (c) CH3CH=C(Br)CH=CHCI (e) CH3CH₂CHOHCHOHCH2CH3 (g) OH НО... CI (h) H3C Br (b) CH3CHBRCHBRCH ₂Br (d) CH3CH(C6H5)CHOHCH3 (f) CH₂(OH)CH2-CH(OH)CH=CHOH CH3 (1) Br HS Br8. 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)
- 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 III1) Identify the stereochemical relationship between the following molecules (enantiomers, diastereomers, same molecule, meso compound) CH3 OH a) and relationship CH2CH3 Br b) and (R)-2-bromobutane relationship HIH DOH H3C CH3 OH c) and relationshipQ8. Draw the two possible chair-like conformations of compound 1. Using the Çabo LAgld erelog priority rules, assign the absolute stereochemistry to each stereogenic centre contained in compound 1. NH2 'F 1
- Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)R and S Assignments in Compounds with Two or More Stereogenic Centers ? Define this ?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? OH