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- A radical substitution reaction is a reaction which occurs by a free radical mechanism and results in the substitution of one or more of the atoms or groups present in the substrate by different atoms or groups.
- Radical reactions involve the movement of individual electrons, we use single-headed curved arrows, and each arrow represents the movement of a single electron.
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- Determine 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 + CH3CH₂OHc. 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 isolableIn an Sn2 reaction with "CN as nucleophile, [CH:CH:CI | CH:CH;OH_ CH;CH;0Tos] reacts faster because it has a [better / poor] leaving group than the other ones. These types of leaving groups can stabilize the developing [positive charge / negative charge / radical] in the transition state thus lowering Jenthalpy / entropy / aetivation energy]. CH;CH2CH2B1 reacts faster in [water/ CH:CN]. In a polar [protic / aprotic] solvent, the negatively charged nucleophile will be solvated thus becoming more stable and [more / less]reactive.
- a- 3. b. N OCH3 C. N Show the for reasonable Curved mechanism the reaction and make sure lone pairs + Conc HBr HBr 40c CN Brew fopics] Draw the major organic product of the reaction shown below. H2SO4 HO, • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. C opy aste [F ChemDoodleplease show the detailed mechanism for each step for the reaction below. OTBDPS Me TMANO (anhydrous) (6 equiv) Co (CO) CH,Cl, -78 °C to r.t. 85% H. Me ОТВОPS triquinane
- 6. For each reaction indicate the predominant mechanism: S,1, S,2, E1, or E2. (a) (b) (c) OH H* H* H* ? ? ? A. A OH OH (d) Br (e) .CI NaBr CH,OH DMSO dilute (CH),COK (9) OTs ? OTs (CH),COH EthanolBr OBn Mg, ether a Work through the above synthesis and draw the structure of compound f. then H3O+ • You do not have to consider stereochemistry. • Draw organometallic compounds as covalent molecules. - #[ ] در ? ChemDoodleⓇ CH3l, NaOH H₂, Pd NaOH H₂N. HAY Previous Next fProvide the reagents in correct order necessory to carry out the following conversion. OCH Br 10 NO, C/FeCls CHaONa, HNO,/ H,S0, excess Br/FeBr3 O excess Bra/FeBrs, Cle/teCl, CHONG HNO:/HSO. Clb/FeClz HNO,/HSO, CH-ONa oxcess Br./feBr O excess Br/FeBr, Cl,/Fecl, HNO,/H,SO, CH ONG
- 1. .CI HC C: Li HC CH LICI 2. -CH3 OH Aqueous HO-S- -CH3 acetone g = SN1 Nucleophilic substitution Electrophilic a = Proton transfer addition h = SN2 Nucleophilic substitution b = Lewis acid/base e = El Elimination c = Radical chain f= E2 Elimination substitution Identify the mechanism by which each of the reactions above proceeds from the mechanisms listed. Use the letters a - i for your answers. among 1. 2.Identify the major product of the reaction of an alkene shown below. ||| 1. Hg(OAc)2, H2O 2. NaBH4, NaOH ....... ОН || IV ОН о, ОНWhich synthetic route(s) would complete the reaction shown? Br || ||| I and II O I and III ? HO OH + enantiomer Synthesis I: 1. NaCCCH3; 2. Na/NH3(I) ;3. OsO4; 4. NaHSO3, H₂O Synthesis II: 2. NaCCCH3; 2. H2, Lindlar's catalyst; 3. MCPBA; 4. aq. H₂SO4 Synthesis III: 1. NaCCCH3; 2. H₂, Pt; 3. MCPBA; 4. aq. H₂SO4