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- Designate sequentially (1,2) the stereochemistry at the numbered sites in the given drawing of vitamin A. J O E,Z OZ, E OZ, Z OE, E Vitamin A OH8. 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)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)
- 1.1 Name the following compound, including R, S, E, Z stereochemistry. arç ÕHConsider the following two structures CI OH ОН ОН HOO H-CI HO- -H H- -ОН A) Determine the configuration of all stereogenic carbons in both structures (R vs. S). Show work! B) Convert the Fischer Projection to a bond-line structure. C) What is the relationship between the two structures? (identical, enantiomer, diastereomer, constitutional isomer, different/not an isomer)Given the following structure and numbering: (a) Label the stereocenters of A as R or S and draw a Fischer Projection of the enantiomer of A with C1on top and C4 on bottom. (b) Draw a Newman Projection of a diastereomer of A looking down the C2-C3 bond with C2 in front.
- Draw each compound in its most symmetric conformation, star (*) any asymmetric carbon atoms, and draw any mirror planes.Label any meso compounds. You may use Fischer projections if you prefer.(a) (2R,3S)-2-bromo-3-chlorobutane11. 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?2. 1. Draw Newman projection and Fischer projection of the following compound and find the configurations of stereocenters. OH CI- Assign the stereochemistry of the following eight compounds as either R or S. H H HO Br HO Br CI H Br A H E .OH Br B TI F 'Br C HO Br L₁₁-CI H G H Br H D
- 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 CHCarbon 4. O Oxygen O Hydrogen What is the stereochemistry of the carbohydrate structure shown above? (A) 2R, 3R (B) 2R, 3S (C) 2S, 3R (D) 2S, 3S (E) Meso3. Which conformation is lower in energy? Explain. (3 pts)