A chemist proposes that the reaction shown hereproceeds by an SN2 mechanism. She carries out thereaction with oxygen-18 (180)-labeled hydroxide in180-labeled water (i.e., 18OH/H2180). When analyzingthe products, she finds that the 180 isotope appearedonly in CH3CO, and not in CH3OH. What does this result suggest about her hypothesis?A CH3H,C-ÖHH3CH,OH3C

Isotopic labelling: It is a technique to identify or to track the isotopes in reaction mechanism. It…

Answered: A chemist proposes that the reaction…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 20E

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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 + Br
Predict 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 ? FeBr3
Complete the reactions given below, write down the type of mechanism (SN1, SN2, E1, E2)?
9) Provide the major product(s) of the following reaction and the corresponding mechanism. NH₂ HNO; H₂SO4
4) 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
(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?
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 Ethanol
1) 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
For 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 why
(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) H₂O
A 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.
Predict the major organic product and draw the complete, detailed mechanism for each of the following reactions. (a) (b) H,CO. H.О (ехcess) ? H2O (excess) ? `CH3 H,SO4 H,SO4 (c) (d) CH3CH20 OCH2CH3 H,O ? H,SO4 `CN Н.О (ехcess) НО H,SO4

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