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- Part D. Do the two structures A and B of each pair drawn below represent the same molecule, constitutional isomers, or stereoisomers? If A and B are stereoisomers, further classify them as enantiomers or diastereomers. H3C Structure A H3C HO H3C H3C Br T H H3C H HO H3CC H C Br HC H H H H CH₂Br CH₂CH3 H CH₂CH3 CH₂OH OH H HO G G H HO H HO G CH3 CH3 CH3 Br Hallo H H3C H Structure B H3C CH3 Br WING H Br HOCH₂ CH3 CH3 HO H CH₂OH H CH₂CH3 H CH₂CH3 H H H H H H Gim CH3 H OH "H ·GII. CH3 HO. OH OH CH3 CH3 OH Relationship of A and BWhich statement is true about these Fischer structures? CH3 CH3 CH3 HO CH3 it: -H HO- -H H- -OH H- HO- -H- H- -OH H- HO- -- CH3 CH3 CH3 CH3 I II III IV O A I and II are identical (same stereoisomers). II and IV are identical. I and II are diastereoisomers. O D.II is a meso structure.1. Below is the Fischer projection of a molecule. Is this the (R) or (S) enantiomer? 2. If you swap the positions of the H and the Cl, does this represent the same enantiomer or the opposite one? 3. Having swapped the positions of the H and CI, if you then swap the Cl and methyl group, what happens to the stereochemistry of the chiral center? CH3 H- CI CH,CH3
- • Question 5: Label each stereogenic center as R or S. CH₂ a. CH₂CH₂ b. CH H 1 NH₂ H CH3 CH₂CH₂ T C. D CI CH3 d. Br C ICH₂ H e. f. H* HO C HOOC CH₂ HO CH(CH3)2 -C₂ C CH3 SH NH₂ H CH3 g. h. .CI CI1a. How many stereogenic centers are present 1c. Draw a three-dimensional structure of a in the structure below? Indicate them with asterisk(s). How many stereoisomers stereoisomers are possible? chiral compound with the molecular formula of C4H4Cl₂ that does not have a stereogenic carbon. In addition, draw the enantiomer of this compound. Number of stereogenic centers: Number of stereoisomers possible: 1b. Draw one of the two most stable stereoisomers of the compound in 1a using a planar structure with wedges and dashes. Now draw it in its preferred chair conformation. 1d. Draw two meso compounds with the molecular formula of C7H14.HN- H3C HN -NH "CH3 OH H. CH3 H,C. Br H3C CH3 CH3 HO. Br HO,
- Use the figure below to answer the following questions. CI Cl CI Molecule 1 Molecule 2 Molecule 3 Molecule 4 Molecule 5 a. Which molecule(s) is/are enantiomers of Molecule 1? b. Which molecules(s) is/are diastereomers of Molecule 1? c. Which molecule is identical to Molecule 1? d. How many different stereoisomers are there for 1-chloro- 3-methylcyclopentanel? e. Which of the following molecules DO NOT rotate light?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 meso4. Draw the enantiomer of each structure that is chiral. Answer by drawing only the enantiomers, not the original structures. HO, O J... CI Cl IZ A Structures for Question 4. CI mi H₂N OH
- 8. The Fischer projection formula for D-mannose, a hexose sugar, is shown below. How many chiral centers are in D-mannose, please circle each Chiral C? HO- HO- H H CHO -H H -OH -OH CH₂OH Number of Chiral Centers and circle each in the structure: Study Guide Practice Questions 9. Draw the structure for 2-chloro-4-methylhexanal 10. What is the IUPAC name of the compound shown below? CH3 CH₂-C CH₂CH₂CH₂CHCH₂Which of the pairs of compounds are enantiomers (optical isomers)? H3C H OH ☐ H₂C-CH₂ CH3CH₂CH₂CHCH3 H3C SH III. C. H H CH₂ Br -CH3 HO H3C H3C- H Br SH CH3CH₂CHCH₂CH3 H₂C- G|||| CH3 H3C- ** H CH₂ H CH3 H CH35. What is the relationship between the molecules? A. Constitutional isomers B. diastereomers C. enantiomers D. meso compound E. identical OH H CH3 CH3 H Br H OH CH₂ CH3 Br H