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- pt. 4: Molecular Models: Stereoisomers me: 4. Using the model of 2-bromobutane representing the R enantiomer from 4., switch any two groups on the chiral carbon. Compare this to your S enantiomer from 4. a. Are they the same or different? b. Are they the same or enantiomers? C. Now switch any pair of groups around the chiral carbon of the "switched" model again! Compare the "double-switched" model with the other unmodified S molecule from 4. Are they enantiomers or are they identical? С. Shown below is the Fisher projection of (R)-2-bromo-(S)-3-chlorobutane. ne mirror image of this stereoisomer and assign the RIS configurations of iral carbons for both isomers. е ll er4. Provide all possible reaction products that would result for the following reactions after an acidic workup (i.e. H3O*). If the reaction products are chiral, label all stereogenic centers as (R) or (S). If they are not, label the compounds as meso or achiral, as appropriate. a. b. C. d. e. CHO + + + + Ph−Li Me-Li DIBAL-H + NaBH4 MgBr1-Methylcyclohexene forms two products when it reacts with bromine in methanol. a. Draw the mechanism for the formation of the products. b. Describe their stereochemical relationship—that is, are they enantiomers or diastereomers?
- 2. In aqueous solution d-glucose (or dextrose) exists in equilibrium between a linear and cyclic form shown below. A. Mark all the stereocenters in the linear form of the molecule. Number them 1,2,3, etc. B. Draw out the reaction that converts the linear form to the 6-membered ring using the arrow formalism. C. Identify the stereocenters in the 6-member ring that correspond to the stereocenters in the linear form marking them as 1,2,3, etc. The reaction also created a new stereocenter. Mark it as H -OH HO--H H--OH нон Ho но HO HO H он H-OH H но.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)1. Draw all possible stereoisomers of the structures below. Indicate the isomeric relationships between all pairs of stereoisomers in each box. In each original structure, circle the stereocenters. A. NHME B. Ph Ph C.
- 5. 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 CH₂CH31. Draw all possible stereoisomers of the structures below. Indicate the isomeric relationships between all pairs of stereoisomers in each box. In each original structure, circle the stereocenters. D. E. NH2 OMe5. 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 compounds
- 5. a. Draw the major product of the following reaction. NaCN Br b. Determine the absolute configuration of each chiral center in the starting material and the product. c. What was the stereochemical outcome at the reaction site? (retention or inversion) Explain. d. The same alkyl halide as in #5a was reacted with excess CH;OH. Three products were obtained, A, B and C. Products A and B are diastereomers and product C is a constitutional isomer of A and B. Draw the three products A, B and C, clearly showing stereochemistry. e. Draw the mechanism using curved arrows to show how the three products in #5d were formed.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?3. What are the configurations (e.g., R or S) of the two stereogenic centers at the top and bottom of methone? Top Bottom.