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- b) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.Identify the electrophile and the nucleophile in each of the following reaction steps and then draw curved arrows to illustrate the bond-making and bondbreaking processes.Explain why quinuclidine is a much more reactive nucleophile thantriethylamine, even though both compounds have N atoms surroundedby three R groups.
- c) Rank the following compounds in order of increasing reactivity toward nucleophiles. Explain your reasoning briefly with reference to structural features. or wy CI AI labeled one of the atoms incorrectly, but I am not sure which. Would the H in HBr be considered a nucleophile as well ?Refer to the reaction energy diagram to answer parts (a) through (e). (a) What is the rate-limiting STEP? (Select from 1, 2, 3, or 4) (b) The TRANSITION STATE for the fastest step is: (c) In the 3rd step which INTERMEDIATE structurally resembles the transition state according to the Hammon postulate? (d) Which STEP NUMBER is endergonic? (e) The number of intermediates in the overall reaction is:
- For an SN1 reaction, which of the following is the correct order from the given statements below: (1) The nucleophile attacks both from the front and from the back of the planar carbocation. (II) The nucleophile attacks from a backside position. (II) The halide ion as the leaving group leaves initially. (IV) The halide ion as the leaving group leaves subsequently. (V) The halide ion as the leaving group leaves simultaneously as the nucleophile approaches. (VI) The product is formed. (VII) A stable carbocation is formed. (VIII) A product with inversed chirality is formed. Nu R-C-X + R-C-Nu whFor each of the following pairs of species, which is the stronger nucleophile in ethanol? Explain. (a) H3C-OH or H,C-o° (b) H3C-OH or H;C-NH, (c) or (d) (е) CH3S` CH3SE (f) CH;Se or or BrFor each pair of aromatic compounds, determine which will undergo electrophilic aromatic substitution faster. (a) (b) (c) (d) LOH ОН CF3 NO, (e) CI CI (f) SO3H SCH3 (g) (h) OH LOH
- Rank the following compounds towards nucleophiles. (1-most reactive - 4- least reactive)Choose all the nucleophiles OH- H3O+ NH4+ CH3OH (CH3)3CLi CH3CH2CH3 NaNH2 CH3SNaFor each pair of compounds determine which will undergo electrophilic substitution faster. (a) (b) (c) (d) CF3 HO Он NO2 () (g) SCH, (e) SO,H OH (h) CI CI HO