13. Draw all potential constitutional isomers and stereoisomers for the compound below; AND point out the type of relationships (e.g., enantiomers or diastereomers) among the stereoisomers; AND find out if there are meso compounds.
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- a)Draw all other stereoisomers of the molecule, labelling meso forms (if any), and assign descriptors to chiral carbon atoms. (b) Including molecule, label pairs of enantiomers and pairs of diastereomers. (c) If you were to distill a mixture of all the isomers, how many fractions could be obtained, and what would in each fraction?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)4. 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
- Draw all the stereoisomers for structures A and B, label each structure as chiral and achiral and give the type of isometric relationship to the original compound be as specific as possible.5B. 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 =4. Provide all possible reaction products that would result for the following reactions after an acidic workup (i.e. H3O*). If the reaction products are chiral, label all stereogenic centers as (R) or (S). If they are not, label the compounds as meso or achiral, as appropriate. a. b. C. d. e. CHO + + + + Ph−Li Me-Li DIBAL-H + NaBH4 MgBr
- Organic Chemistry, Ch.4, WS #2, Stereochemistry - Review of R&S configuration, Fischer Projections, Enantiomers, Diastereomers, Meso Compounds. 1. Assign R or S configuration to each stereocenter. (a) H₂C H₂C a H- H OH CH₂CH₂ - Br CH, (b) 2. For each Fischer Projection, assign R or S configuration. CH₂ CH₂CH₂ b. H₂N- H COOH + -H CH₂ C-OH (c) HTC OH CH₂OH C. Br- CH₂OH CI CHO CH3.) Which structure is a meso compound? А. В. С. D. CH3 CH3 CH3 CH3 H--C1 H--Ci H--c1 H--Cl Cl-- CH3 Cl--H H--c1 Cl--H CH3 CH2CH3 CH2CH3 A. Structure A B. Structure B C. Structure C D. Structure D Keywords: chiral, achiral, meso, internal, stereogenic center, asymmetric carbon, mirror-plane, absolute configuration, symmetry Concepts: Stereoisomerism, chirality3), compounds, enantiomers, diastereomers, or constitutional isomers). The same answer can be used more than once. For the following pairs of compounds, indicate the relationship (identical (a) (b) H H H HO CO,Me MeO,COH NH2 NH2 H. HN -NH2 MeO,cT'OH H. HOTCOME H (c) H CHCH3 (d) CH3 Br. H H он Br- -CH,CH, Br H +H H- Br -H H H HO- -H CH3 H3C- Br -Br ČH3 ČH3 3
- • PRACTICE PROBLEM 5.22 Write three-dimensional formulas for all of the stereoisomers of each of the following compounds. Label pairs of enantiomers and label meso compounds. enslg a nsudomotaib esvierd ofni oluelom oreovb dase to ope.n 1oim s ier 1erto (a) ibaong (b) A boemo OH (c) CI ОН CI F F OH win vle (f) HO,C. (d) (e) OH CI CO,H Br im slm (b) OH Tartaric acid3. Give the relationship between each pair of molecules below (diastereomers, enantiomers, or identical). Answer for the whole molecule, not just the particular conformation shown, and note that molecules may not necessarily be shown using the same style of drawing. (a) (b) (c) H3C H3C Н ОН Н OH CI обо (d) OH CI ОН 4. Assign R or S to all chiral centers in the molecules in question 3. OH H3C. H3C OH ОН OH НIdentify the relationship between the following pairs of structures, then state whether they are enantiomers, diastereomers or identical. Help me answer iv., v., iv., vii. (last 4 sub part)