A chemist proposes that the reaction shown here proceeds by an SN2 mechanism. She carries out the reaction with oxygen-18 (180)-labeled hydroxide in 180-labeled water (i.e., 18OH/H2180). When analyzing the products, she finds that the 180 isotope appeared only in CH3CO, and not in CH3OH. What does this result suggest about her hypothesis? A CH3 H,C-ÖH H3C H,O H3C
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- (d) Consider the following catalyzed and non-catalyzed pathways of a substitution reaction of bromoethane. Draw an energy diagram for each of the following reactions (label all axes and include reactants, intermediates (if any) and products). CH3CH₂Br + HO CH³CH₂OH + B (non-catalyzed) ное CH3CH₂Br + CH3CH₂OH + 1 (catalyzed) CH3CH₂ + BrPredict the major product(s) of each of the following reactions. Draw the complete, detailed mechanism that leads to the formation of each of those products. (b) (c) (a) HO;S HNO3 Cl2. ? H,SO4 ? FeCl3 AICI3 H3CO (d) (e) Br2, ? conc HNO3 ? FeBr3Complete the reactions given below, write down the type of mechanism (SN1, SN2, E1, E2)?
- (f) This part of the question refers to the substituted alcohol (N) given below. HO CH3 Br (i) Classify N as a primary, secondary, tertiary or quaternary halide. (ii) Based on this classification, which reaction mechanism (SN, or SN2) would you expect N to undergo faster? why?9) Provide the major product(s) of the following reaction and the corresponding mechanism. NH₂ HNO; H₂SO44) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3
- In which of the following reactions would you expect a carbocation rearrangement? Explain. Hint: You will need to figure out whether the predominant mechanism is Sn1, Sn2, E1, or E2. (a) (b) (c) OH H+ H+ H+ A OH ОН (d) Br (e) .CI NaBr ? CH;OH ? DMSO (f) dilute (CH3)3COK (g) OTs ? ? OTs (CH3);COH EthanolFor SN1 Explain the order in which 2o (secondary) alkyl halides reacted (fastest to slowest) and explain why. 2o (secondary) compounds listed are: (see picture) 2-chlorobutane 2-bromobutane bromobenzene bromocyclopentane bromocyclohexane Base your explanations on the following considerations: the nature of leaving group, the effect of structure, steric hindrance and any other feature. Be sure to explain which alkyl halides did not react and why1) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors (structures), the regiochemistry that results in each case. OMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3
- (j) (k) Predict the major product or the necessary reagent or reactant to complete each of the following reactions. In the box before each reaction, indicate the mechanism followed by the reaction. (Free radical (FR), SN2, SN1). (h) + KBr CH3 1 2 CI CH3 -H -CH3 CH₂CH3 NEC Na+ (i) Na+ N3 Br₂, light CH3CH2 Hu Br 'H (k) H₂OA student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.According to the rules for reasonable mechanisms, the E1 reaction shown here should undergo a 1,2-hydride shift. However, the same product is produced regardless of whether the rearrangement occurs. Br H20, heat (a) Draw the mechanism that includes that carbocation rearrangement. (b) Draw the mechanism that does not include the rearrangement. (c) Experimentally, how can we use 13C isotope labeling to determine whether the rearrangement occurs? In other words, can a 1ºc atom in the substrate be replaced by a 1°C atom so that the E1 products would depend on whether the rearrangement takes place? (d) How can we use deuterium isotope labeling to determine whether the rearrangement occurs?