17. What can you say about the reaction below? 1. OsO4 2. NaHSO3 ? A. This reaction will generate cyclohexanol B. This experiment will generate cis-1,2-cyclohexanediol C. This reaction will generate a mixture of R,R-1,2-cyclohexanediol and the S,S-enantiomer D. This experiment will generate trans-1,3-cyclohexanediol E. This reaction will follow Markovnikov's rule
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- The bromination of 2-butene is an exergonic reaction. Br H3C. H;C. Br, CH3 CH3 Br a. Draw the mechanism for the reaction (you may ignore the stereochemistry for this question). 2.Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed. a. cis-2-pentene + Br2/CH2Cl2 b. trans-2-pentene + Br2/CH2Cl2 c. 1- butene + HCl d. methylcyclohexene + HBr e. trans-3-hexene + Br2/CH2Cl2 f. cis-3-hexene + Br2/CH2Cl2 g. 3,3-dimethyl-1-pentene + HBr h. cis-2-butene + HBr i. (Z)-2,3-dichloro-2-butene + H2, Pd/C j. (E)-2,3-dichloro-2-butene + H2, Pd/C k. (Z)-3,4-dimethyl-3-hexene + H2, Pd/C l. (E)-3,4-dimethyl-3-hexene + H2, Pd/C10. Write out the mechanism (intermediate/transition state) for this reaction. Indicate stereochemistry in product. H₂C Br H KOH S2
- 2. For the following nucleophilic substitution reaction: NaOC(CH3)3 CH3 'CH3 CH3 a. Draw the first transition state (TS1), the reaction intermediate, and the second m transition state (TS2) in the labeled boxes. Make sure to show any formal charges, unfilled p-orbitals, and correct stereochemistry. TS₁ 41001 Intermediate ogmos TS2 amond- b. Which of three molecules you drew for part 'a' is lowest in energy? Write your answer in the box below. c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use wedged and dashed lines to clearly show the resulting stereochemistry at each chiral center. If there is more than one possible product, draw one in each box - if not, leave one box blank. CH3 Br + NaOC(CH3)3Chemistry 4. Draw the correct product (may be multiple competing products) and label each of them as the product of E1, E2, SN1, or SN2. Br oner Br- OTS KCN DMSO NaOH H₂O, heat H₂O CH,CH,ONa CH₂CH₂OH NaSH DMSO KOH DMSO NINH, NH₂ NH₂ please explain6. Circle the product of the following reaction. 1. C=C-H 2. H2O НО Н H H3C . I H3C OH Н || Н сан Н Н.с о IV H Н
- a. Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement. b. Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D+ reacts like H+.)3. Provide the mechanism for the following rxn: ethanol heat Br a. CH3 CH3 NAOCH3, CH3OH Br b. D H OH H,SO4 с.1. For the reaction scheme of the hydroboration step of 1-hexene. BH 3 THF BH₂ BH₂ a. Draw the transition states leading to each of the two regioisomeric products shown. Label all partial charges in your transition states. b. Which of the two transition states is lower in energy and WHY? Be sure to include both an electronic argument (optimized placement of partial charges) and a steric argument. +
- Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 Br2 / FeBr3 • You do not have to consider stereochemistry. Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one. OO. #[ ] در ChemDoodle CH3 BrA terminal alkyne (RC=CH) is exposed to excess HBr. What rule should be followed to determine the placement of the halogen atoms in the product? A. Markovnikov rule O B. Hofmann's rule O C. Zaitzev's rule D. Anti-Markovnikov ruleSECTION 6: Show the mechanism of each reactions with arrows and intermediates form as in a. b. C. HBr Br₂ Cl₂, H₂O Br Br CI Br OH