For each of the substrates below, identify whether: (A) the rate of substitution doesn't depend on nucleophile concentration and (B) the product distribution from substitution gives a 50/50 mix of enantiomers. If you answered "yes" for the first susbtrate, draw the intermediate that forms during a nucleophilic substitution reaction in the space below the table. Substrate Are both A and B true? Br. P Oyes Ono Oyes Ono Oyes Ono CI Oyes Ono X olo Ar

For each of the substrates below, identify whether: (A) the rate of substitution doesn't depend on nucleophile concentration and (B) the product distribution from substitution gives a 50/50 mix of enantiomers. If you answered "yes" for the first susbtrate, draw the intermediate that forms during a nucleophilic substitution reaction in the space below the table. Substrate Are both A and B true? Br. P Oyes Ono Oyes Ono Oyes Ono CI Oyes Ono X olo Ar

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.45P: Draw a structural formula for the major organic product of each reaction and specify the most likely...

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For each of the substrates below, identify whether: (A) the rate of substitution doesn't depend on nucleophile concentration and (B) the product distribution from substitution gives a 50/50 mix of enantiomers. If you answered "yes" for the first substrate, draw the intermediate that forms during a nucleophilic substitution reaction in the space below the table
For the following sets of substitution reactions that occur via an SN2 mechanism, draw the main organic substitution product (i.e., not the leaving group, for each reaction draw the product, though the products may be equivalent) and indicate which reaction occurs at the faster rate. (a) H3C CH₂O H3C E H3C Br (b) Br CH3O H3C + H3C-Br CH3O- H3C-Br
Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed. (g) CH3CH2ONa++CH2=CHCH2Clethanol
The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
When performing a nucleophilic substitution reaction and not knowing the structure of the starting material or product, how can you form a method to determine whether the reaction proceeds via an SN1 or SN2 mechanism?
Step 4a: Classify step. The target product is present, but the reaction is not over. The ethoxide ion has been regenerated. :0: :0: What is the key process in the next step of the mechanism? proton transfer formation of a o bond between nucleophile and electrophile loss of a leaving group carbocation rearrangement (e.g., methyl or hydride shift)
In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?
Using the pKa values of the conjugate acids of the leaving groups (the pKa of HBr is -9, and the pKa of H2O is 15.7), explain the difference in reactivity between CH3Br and CH3OH in a nucleophilic substitution reaction.
Nucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure via resonance. For the reaction below, draw the structure of the stabilized reaction intermediate in the box below. CI F3C CF3 NO₂ F3C N CF3 NO₂ • You do not have to consider stereochemistry. • Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than one resonance structure is possible, only draw the most important one.
For the reactions below predict the product that will form via the stated mechanism then explain why using the stated effect the reaction will proceed through the supplied mechanism
H3C-C O: H ethanal :CN: and the electrophile is cyanide ion In the step you have just written, the nucleophile is slow rate-determining Ö—0—1 H3C-C-C=N; adduct
Determine the major product of the following reaction. For basic nucleophiles, you can assume there was a follow-up protonation step to create the alcohol functional group. You can ignore stereochemistry for this assignment. 3) 1) Br2, H₂O 2) NaOH : Br-Mg.