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- 9:PV : Organic chemistry 1 Assignment. (. 3 Which of the following groups has the highest priority according to the Cahn- * ?Ingold-Prelog sequence rules )1 نقطة( CH3 CH2OH O CHO CH2CI O How many chiral center the amoxicillin ? have )1 نقطة( NH2 H -N- HO СООН amoxicillin II エーそ4. The [a] of pure quinine, an antimalarial drug, is -165°. a) Calculate the enantiomeric excess (EE) of a solution with the following [a] values: -83°. H3CO HO Hin Quinine (anti-malaria drug) b) Calculate the percent of each enantiomer present. c) What is [a] for the enantiomer of quinine, and does it rotate light clockwise or counterclockwise? ( d) Identify 2 functional groups in quinine. (.. e) What are 2 properties that are different between the R and S enantiomer.5) 1) MeO'Na* &r=&r MeOH 2) work-up (HCI, H₂O) 7) 8) NH OH 1) NaOH, H₂O 2) work-up (HCI, H₂O) HCI, H₂O heat 'H HO HO HCI, H₂O OH NH, CH How many stereoisomers are possible for this cyclic hemiacetal? OH
- A)Circle all of the stereo centers in MDMA. B) assign the absolute stereochemistry (R or S) for each stereo center4. (+)-Tartaric acid has a specific rotation of +12.0°. Calculate the specific rotation of a mixture of 68% (+)-tartaric acid and 32% (-)-tartaric acid. CThe absolute value of the specific rotation of an enantiomer 2-butanol is 13.5o. What is the percentage of each enantiomer (R and S) in a mixture that has a specific rotation of -8.5o? The (R)-enantiomer is levorotatory. Be clear and detailed.
- 1. A solution has 80% (R)-2-bromobutane and 20% (S)-2-bromobutanea. What is the “enantiomeric excess” of (R)-2-bromobutane? b. If pure (R)-2-bromobutane rotates light 100º to the right, how much rotation would occur for a solution with 80% (R)-2-bromobutane and 20% (S)-2-bromobutane c. If a solution has a 50/50 mixture of (R)- and (S)-2-bromobutane, what would be the enantiomeric excess and the optical purity? 2. A mixture of two enantiomers has as observed rotation of -18°. The specific rotation of the (-) enantiomers is -27°. Find the % of the two enantiomers in the solution.4. The [a] of pure quinine, an antimalarial drug, is -165°. a) Calculate the enantiomeric excess (EE) of a solution with the following [a] values: -83°. b) Calculate the percent of each enantiomer present. H3CO d) Identify 2 functional groups in quinine HO Hin Quinine (anti-malaria drug) c) What is [a] for the enantiomer of quinine, and does it rotate light clockwise or counterclockwise? (5) For the following reactions: a. Complete the reactions with both possible chiral products. b. Determine and label the absolute configuration (R or S) of all stereocenters. c. Label the reaction type and the stereochemical relationship (meso, enantiomer, diastereomer, or none). d. Draw out the reaction mechanism showing lone pairs, arrows, bond making/breaking, etc. for each reaction. CH (R) CH, (S) OsO,, NAHSO, a) (S)oH (R H. Reaction type Cis Hydroxylation Stereochemical Enantiomers Relationship Mechanism: EXAMPLE MECHANISM (you do not need to know this mechanism for Chem 345) Rapent tove ut oppastasde OH HO. OH
- Which of the following compounds will elute FIRST from a column separated using reverse-phase liquid chromatography? OH O CH₂4. 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 MgBr7.(a) Draw and label (i) the enantiomer and (ii) a pair of diasteromers of the following compound. OH (b) Will a 50:50 mix of the enantiomers that you drew for 7al be optically active (rotate plane polarized light). Explain the reason for your answer b) Will a 50:50 mix of the two diasteriomers_you drew for 7bii be optically active (rotate plane polarized light). Explain the reason for your answer