Ⓡ 5. Assign the R and S configurations for all stereogenic centers in the following compounds. H BI!!!! Br Br WOH H₂C H CH₂ H -H CH₂ CH(CH₂)₂ (b) CH=CH₂ H+C=C -C=CCH₂ CH₂CH₂CH₂C1 CH₂CH₂Cl H₂NH CH₂CH₂Cl CH₂CH₂CH₂OH H₂N CH₂CH₂OH
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- (A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.Department Final EXd Q1: Coibacin B is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites. HAH H (a) Assign the configuration (R or S) of each chiral center in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes is fixed.(−)-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.
- 11) How many possible stereoisomers does the following compound have? CH(CH32 H3CM H3C H.8. 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)18 Mark each stereocenter in these molecules with an asterisk. Note that not all contain stereocenters. (a) OH CH, N. `CH3 (b) OH (c) HO, NH2 (d)
- VIII. Assign R, S configurations to each chirality center in the molecule below. Br CH3 X OH CH3 I I (4. · For each pair of structures shown below indicate whether the two compounds are constitutional isomers, not isomers, configurational diastereomers or configurational enantiomers of one another, identical compounds (meso), or identical compounds (not meso). and CI .CI "CH3 "CH3 ОН CH3 -CH3 НО and H3C- ОН H- CH3 H OH H Br Br LCH3 CH3 and H H3C" ČI CH3 H3C H. H and H and4. 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 Br
- 5. 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 CH35. a) How many stereocenters does this compound have? CH¸Br b). How many stereoisomers are possible for this compound?1. How are each of the structures A-F related to structure X? They could be E (enantiomers), D C (conformers), or I (identical). (diastereomers), CH3 CI -Br HOH₂C- -OH CI X НО, H3C H₂C D CI Br CH₂OH CI HO STEREOISOMERS Br A CH2OH CI Br CI HOH₂COH CI CI Cl CH3 OH E -CH3 -CH₂OH B Br Br НО. Br CH3 HOH₂C CI C CI CH3 HO CH₂OH F