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- c. Snl reactions dominate under polar protic solvents. Increasing the polarity of the solvent will increase the rate of the reaction because the polar solvent will stabilize the dispersed charges on the transition state more than it will stabilize the neutral reactant. Label areas of ô* and & on the molecules of the transition state of the SN1 reaction below: Me Me Ме Me Me H20 Br -Br OH + НО \'H Et Et RDS Et H Et Et transition state not isolable carbocation intermediate not isolablereactions. Draw mechanis.mandspecify What are the products fallowing the their slereachemistry CH3 H202Determine the mechanism of nucleophilic substitution of each reaction and draw the products, including stereochemistr CH₂CH3 CI Br + CN d. + CH3COOH a. acetone + -OCH3 e. DMF f. b. C. ||||| a ||||| Br H Br CH2CH2CH3 + CH3OH DMSO H CH3 CI Br + OCH₂CH3 + CH3CH₂OH
- 2. Draw the complete mechanism for the following reactions, showing the formation of each product. Include all formal charges, electron-pushing arrows, and resonance structurac a. b. Et NO₂ Br Me. Me 1. NaOH, H₂O, heat 2. H₂O* CI 1 major product 1. NaOH, H₂O, 300 °C 2. H₂O* (acidic work-up) Hint: Show Meisenheimer complex (intermediates stabilized by resonance) TeoM 3 major products HAM amenn O eM 181 9Gve the major product of the following reaction. CH,CH,ONa H. HO. HO. L There is no reaction under these conditions or the cor«.Lproduct.is not fisted here,Give the mechanism and the major product of the rxn., Show all stept H3C .- bulky... ph Br Strons Ph) Na O CH₂ сизон non- T=70°
- 2) Formulate the products for all reaction steps of the sequence. Br sformation. Br 1) E107 2) E107 OEt 3) OH" 4) H30* 5) AT irs, andWhich conditions will produce the target product in the highest yield? O A) 1. BH3; 2. H₂O₂, NaOH, H₂O B) 1. OsO; 2. S(CH3)2 C) 1. Hg(OAc)₂, H₂O; 2. NaBH4 D) H₂SO4, H₂O A ? B OH racemic mixturea- 3. b. N OCH3 C. N Show the for reasonable Curved mechanism the reaction and make sure lone pairs + Conc HBr HBr 40c CN Br
- 6. Determine whether the following reactions are SN1 or SN2. Draw the mechanism and the products with stereochemistry. a. b. Br Br + "CN + -OCH 3 acetone DMSO d. e. f. Br 11 + CH3OH + CH3CO₂H Dº Br + -OCH₂CH3 + CH3CH₂OH DMF 1, 2 of 2(BUOK (BUOH, heat d. (BUOH, heat EESH e minimum temp NaCN Br acetone minimum temp EISH Br minimum temp 5. Mechanisms. Give the mechanism for each rx above as indicated. Use additional sheets as needed. c. (rx 4c) f. (rx 4f) g. (rx 4g) DELLOTS OTS 4) Consider the two E2 reactions above. KOtBu DMF heat KOtBu DMF heat a. What are the major products for each reaction? b. What is the mechanism for each reaction? c. Which reaction would be faster and why? Use words like "transition-state, intermediate and/or reactant/product stability" in your justification. Draw the reaction coordinate diagram for both to assist in your explanation.