WS-3.26: Assign the absolute stereochemistry in the following mor draw the enantiomer of each compound. 1. 2. OH HỌC TỊCHỊCH, Br OH H CH3 OH CH₂
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- 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 CHWhich statement is correct about stereoisomers A, B, and C? H- CI CH3 S S CH3 A CI -H CI H A and B are enantiomers, C is a meso compound. A and C are enantiomers, B is a meso compound. A, B, and C are all meso compounds. Band C are enantiomers, A is a meso compound. CH3 R R CH3 B -H - CI H- H CH3 S R CH3 C CI -CIIdentify whether the following pairs of compounds represent a pair of constitutional isomers, different conformations of the same compound, configurational isomers, identical structures, or unrelated compounds. If the molecules are configurational isomers, identify if they are enantiomers or diastereomers. Build models of the molecules to help you. Order of determination: a. Constitutional isomers (determine name with numbering system). b. Configurational isomers (determine R/S or cis/trans) c. Conformational isomers (if the above are the same, is the spatial arrangement different?) d. Identical (if all of the above are the same) J. Br Br ÇH3 and HO,C ÇH3 Br Br K. H3C Br and CH,CH3 CH;CH Br CH3 CH3 H3C. CH3 & Br Br Е. H HgC CH3 H CH3 & CI CI CI I- I
- 3.4 How are the following molecules related? Br Br ÕH 3.4.1 identical 3.4.2 enantiomers 3.4.3 diastereomers 3.4.4 functional isomers 3.5 What is the correct stereochemical name for the following compound? CI Br 3.5.1 (2S,3S)-2-bromo-3-chlorobutane 3.5.2 (2R,3R)-2-bromo-3-chlorobutane 3.5.3 (2R,3S)-2-bromo-3-chlorobutane 3.5.4 (2S,3R)-2-bromo-3-chlorobutane8. 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)3. Give the relationship between the following molecules. Your options are enantiomers, diastereomers, or the same molecule. Determine R/S configurations of any chiral a. b. C. centers. H₂C-Si- H H CH3 COOH H -OH H-OH H -OH CH₂OH H₂ Br CH3 CO₂H Br H CH₂OH and HO H- HO H CH₂OH H -ОН H COOH and H₂C H H- Br Si CH3 CH3 CO₂H -Br -H CH2OH
- What are the stereochemical designations in the following substance? A.) 2S, 4S B.) 2S, 4R C.) 2R, 4S 5.) 2R, 4R5. different compounds b) that are not isolielss bicucional isomers! a) How many stereocenters does this compound have? How many stereoisomers are possible for this compound? Write most under the memb NH₂ most stable. each trio which is least stable. NH₂Determine the relationship between the following compounds (Enantiomer, Diastereomer, Meso, same) indicate R or S, E or Z for each stereocenter. a. F OCH3 H b. ∞ ∞ C. F II H OCH3 -OH -OH OH HO H- O -H -OH OH I
- 2. (6) Draw trans-1-chloro-3-ethylcyclohexane in the box below and assign the stereocenters (doesn't matter which enantiomer you draw). Then draw any diastereomer, any chiral constitutional isomer (+1 XC draw any one achiral constitutional isomer) C, = R or S C3 R or S trans-1-chloro-3-ethylcyclohexane Any diastereomer CHIRAL constit. isome ACHIRAL constit. isomerWhich of the following compounds is an enantiomer of compound X ? CH₂ H₂C C CH3 OH 1 Select one: A. I OH O B. III O C. II H₂C- X H₂C || OH -CH₂ OH -CH₂ OH H₂C- CH₂ -CH₂ OH E OH |||5. For the following: Answer I, II, III and/or IV CH3 ÇH3 ÇH3 CH3 но- HO-- но- - H HO- H- HO- но- H. HO- но H- H- C2H5 C2H5 C2H5 C2H5 III IV ... a. Which structure is an enantiomer of I? b. Which structure is an enantiomer of III? c. What two structures are diasteriomers of II?