Draw all stereoisomers of 1,3-dimethylcyclohexane. Label them as enantiomers/diastereomers to each other. Do not draw more than 1 of the same molecule (ie watch out for meso) Repeat for: HO a. b. OH
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- 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?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 CH₂OH5. Draw the structure of (S)-1-bromo-1-chloropropane. Take care to indicate the three- dimensional stereochemistry properly. 6. How many chiral centers does the following compound contain? CH3 7. Label each chiral carbon in the molecule below as having R or S configuration. HO₂C H F. H3C H CH₂CH3
- 4. For each of the following molecules, label each stereocenter as R or S. Label the molecules appropriately as chiral or meso. a. b. methionine NH₂ H d. но. OH c. D = 2H, T = ³H, isotopes of hydrogen. f.T. OH OH CI Y ОН4. Draw the compound, 2-pentanol, shown on the PubChem website. Label any stereocenter(s) as to their absolute configuration, e.g. R or S. 5. Is there a plane of symmetry in 2-pentanol, yes or no? 6. Is 2-pentanol chiral or achiral?1. Is the molecule shown below chiral or achiral? HO₂C OH 2. Is the molecule shown below chiral or achiral? CH₂OH H OH CO₂H 3. Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound. CH3 & D ....!!!!! H3C Holl 4. Label each chiral carbon in the compound below as R or S. JOH // CH3
- III. Consider the compound below. H. F HO- HO -HO- (Atomic number: H-1, C-6, O-8, F-9) a. How many chiral centers are in the molecule? b. How many stereoisomers are there for the compound? c. Draw the Fischer projection for each of the stereoisomer and determine the absolute configuration (R or S). Label each using I, II, etc. d. Which pairs are enantiomers? Which are diastereomers?5. CIRCLE ALL THAT APPLY: Why is it so difficult to physically separate enantiomers from each other in a mixture? a. They are the same compound b. They have the same melting points c. They have the same densities d. They are both meso compounds2. Label any stereocenters in the following molecule as (R) or (S): ОН H. .CH3 `CH3 ОН
- Use the skeletal structure provided. CI OH HO .. A. provide the Fischer projections of the skeletal structure shown B. provide the structure (Fischer or skeletal) of a constitutional isomer C. provide the structure (Fischer or skeletal) of the enantiomer isomer H3C CH3 D. provide the structure (Fischer or skeletal) of a diastereomer isomer indicate if the structure can be classified as a meso compound. O Yes, meso O No, not meso3. 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 CH2OH8. 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)