4. (A) A medicinal chemist wished to make a series of aromatic molecules bearing a ketone andthioether group with ortho, meta, or para relationships. To achieve this, they propose usingnucleophilic aromatic substitution treating the corresponding ortho, meta, and para arylchlorides with sodium ethanethiolate (NaSEt). Predict which of these reactions will likelywork and which will likely fail. Provide a mechanistic explanation why.SET ONasEtEtSglagol Glal olheatEtStarget moleculesEtS(B) Would the analogous reactions using EtMgBr instead of NaSEt be more or less likely to work?Explain why or why not.لمسلمEtMgBr

Answered: 4. (A) A medicinal chemist wished to…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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4. (A) A medicinal chemist wished to make a series of aromatic molecules bearing a ketone and
thioether group with ortho, meta, or para relationships. To achieve this, they propose using
nucleophilic aromatic substitution treating the corresponding ortho, meta, and para aryl
chlorides with sodium ethanethiolate (NaSEt). Predict which of these reactions will likely
work and which will likely fail. Provide a mechanistic explanation why.
SET O
NasEt
EtS
glagol Glal ol
heat
EtS
target molecules
EtS
(B) Would the analogous reactions using EtMgBr instead of NaSEt be more or less likely to work?
Explain why or why not.
لمسلم
EtMgBr

Expert Solution

Step 1: 4. A) The detailed solution is given below,

A nucleophilic substitution reaction is a type of organic reaction where one nucleophile replaces another.

When nucleophilic substitution reaction occurs at ortho, meta, and para only ortho and para are possible not neta position.

The electron-withdrawing group's ortho or Para position to the leaving group is preferred to substitution as resonance stabilized. In contrast, meta is stabilized by the inductive, but no resonance.

The carbonyl center is the hard center and the benzene ring having Cl is the soft center and NaSEt is the soft reagent so NaSEt will attack at the Soft center. (Soft reagent will attack at the Soft center and hard reagent will attack at the Hard center)

The detailed mechanism is,

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