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Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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
Transcribed Image Text: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
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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 enantiome 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 Oyes Ono CI Oyes O no J... Oyes Ono Oyes Ono Click and drag to start drawing a structure. :☐arrow_forwardFor 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 enantiome 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 Br 2 .. Are both A and B true? Oyes Ono Oyes Ono Oyes Ono Oyes Ono Click and drag to start drawing a structure. X 5 ㄖˋ X 2:0 G €arrow_forwardFor 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 yes no CI yes no 25 yes no yes no Click and drag to start drawing a structure. X G ☐: Parrow_forward
- 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-Brarrow_forwardDraw 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=CHCH2Clethanolarrow_forwardThe 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.arrow_forward
- 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?arrow_forwardUsing 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.arrow_forwardPropose a mechanism for the conjugate addition of a nucleophile ( Nuc:" ) to acrylonitrile ( CH,=CHCN ). Use resonance forms to show how the cyano group activates the double bond for conjugate addition.arrow_forward
- 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.arrow_forwardWrite a reasonable mechanism for the following transformation.arrow_forwardPredict 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). (b) (a) Cl₂ CH₂CH₂OH (a) 1 hv 2 (b) H Br H₂O Na+ SCH3 (c) (d) CI "CH3arrow_forward
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