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- 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 CH₂OHHO H. a) Provide the R-S configuration for each of the following chiral centres. b) Provide the drawing and R-S configuration for one diastereomer of the above molecule. c) Bonus: Come up with a molecule that is a constitutional isomer of the above molecule and has the same amount of chirality centres and R-S configurations. For example: if the above molecule has 10 R and 10 S chiral centres, provide a constitutional isomer that also has 10 R and 10 S chiral centres.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 CH
- Indicate whether each of the following pairs of compounds are identical, enantiomers, diastereomers or constitutional isomers. (i) CH2 HÇ OH HO H. and H;C" H3C" CH (ii) and (ii) СНО CHO H. OH- H HO- and H. -HO- НО -H- CH,OH ČH,OH (iv) ÇH3 H3C. CH3 H. CH3 and H. CI CI H. H.Of the four structures shown here in Fischer projections, indicate the relationships between (a) and (b), and between (c) and (d)? CHO CHO нтон нотн CH₂OH (a) CH₂OH (b) ÇO₂H H-OH -OH -он но- HO- CO₂H (c) II HO-H ÇO₂H of A. Both pairs are enantiomers O B. Both pairs are identical C. (a) and (b) are enantiomers, (c) and (d) are identical D. (a) and (b) are identical, (c) and (d) are enantiomers II CO₂H (d)11. Consider the following compounds: ÇO,H CHO ОНС H. ОНС CO,H H3C- -- H. HO- H3C H. O, H ČOH HO, CH3 B (a) Label the asymmetric carbons as R or S on each compound (A - C). (b) Which compounds, if any, are enantiomers? diastereomers? identical?
- 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. Do the following structures represent the same molecules or pairs of enantiomers? Additionally, convert the perspective structures to Fischer projections and vice versa. a. b. C. d. 11 CH HOH₂CH₂C-COH CH₂Br H₂C-CCI CH₂CH3 CH₂Br H-OH CH3 CI HỌC CHỊCH H CH₂CH3 CI HẠCH,C-C 'CH, CH₂Br H₂CH₂C-CH₂CH₂OH OH H HO-CH3 CH₂Br CH3 0-5-6-5 H+CI CH CH₂CH3CH3.. -Br CH;CH2 mirror plane Draw the Fisher projection of the R enantiomer of 2-bromobutane below 3. the R enantiomer of 2-bromobutane. Retain the model you made of the S initials Secure the initials of your TA after showing them your physical model of 4. enantiomer intact on the side. 23 ch are of the mode of the chiral carhe .Is you drew be
- 5. Consider the following pairs of structures. Identify the relationship between them (enantiomers, diastereomers, or identical compounds. H3C OH H₂C HOITY H CH₂OH HO HO C,, CO₂H вой HOH2C CH₂ OH H OH H OH Н HO H H COzH Br Д H3C Br H₂CH₂C CI H CHO CH3 I CH3 OH HO Н HO... HO C OHC Н H3C, Bell!! H CO₂H Н.С CH₂OH H OH H OH HO H CH₂ CO₂H HỌ,H CH₂CH3 CH3 CI CH₂OH Br5) For the following reactions: a. Complete the reactions with both possible chiral products. b. Determine and label the absolute configuration (R or S) of all stereocenters. c. Label the reaction type and the stereochemical relationship (meso, enantiomer, diastereomer, or none). d. Draw out the reaction mechanism showing lone pairs, arrows, bond making/breaking, etc. for each reaction. CH (R) CH, (S) OsO,, NAHSO, a) (S)oH (R H. Reaction type Cis Hydroxylation Stereochemical Enantiomers Relationship Mechanism: EXAMPLE MECHANISM (you do not need to know this mechanism for Chem 345) Rapent tove ut oppastasde OH HO. OHConstruct models of 1,2-dibromocyclopentaneand draw all the possible stereoisomers. Label each chirality centre with an*,andan Ror S. Indicate clearly which pairs are relatedasenantiomers and which as diastereoisomersor meso.