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Solved in 4 steps with 1 images
- 7. For each of the following pairs of species, encircle the stronger nucleophile in acetone? (a) H3C-OH or H,C- (b). H3C- or H,C-OH2 (c) H3C-OH or H3C-NH2 (d) o (e) () or or or NH (h) CH,S CH;Se or or NH PH (1) CH,Se or BrFor 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 BrWhich compound would react faster by an SN2 process? H3C CH3 H3C,,, CH3 H3C,,, CH3 A B 0 Br (A) Br Br (B) (C) H3C Br (D) CH3
- Draw the mechanism and predict the major product for each of the following reactions. (a) (b) CH3 (c) NH H3C. 1. LIAIH4, ether 1. LIAIH4, ether NaBH4 .? ? H,O 2. H20 2. H,о CH3(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 + Br6) Complete the following mechanism. (D and SN2) H Br. NaH "H: " 7) Complete the following mechanism. (D and SN2) H NaH "H: " Br. SN2 Good Nucleophile SN2 ether THF
- (b) Which of the following will react most slowly with cyanide nucleophile (NC-) in an SN1 reaction? .CI Br Cl1. Elementary steps: 1.) Identify the nucleophile and electrophile for each step. 2.) Provide the mechanism using curved arrows. 3.) Then identify which elementary step is it? (a) (b) (e) H₂O: H₂O: the (c) (1) \:NH3Refer 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:
- (1) Identify the nucleophile and electrophile for each step (2) Provide the mechanism using curved arrows (3) Then identify which elementary step it isWhich is the major substitution product of the reaction shown? (A) OEt (C) (E) no reaction Br NaOEt © 2019 ProtonGuru.com (B) (D) OEt (F) a mixture of more than oneIn 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 Ethanol