The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the final product. Show the mechanism of addition and the structure of the final un-charged addition product.

The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the final product. Show the mechanism of addition and the structure of the final un-charged addition product.

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...

See similar textbooks

Similar questions

Show how the following compound can be prepared by a malonic or acetoacetic ester synthesis (or other B-dicarbonyl) reaction:
An alternative procedure for preparing the amine of Step 3 is reductive amination of the corresponding ketone. What is reductive amination? Why might this two-step route for formation of the amine be preferred over the one-step reductive amination?
Draw the major product formed from Hofmann elimination of the following amine.
Mandelate esters exhibit spasmolytic activity (they act as muscle relaxants). The nature of the alkyl group (R) greatly affects potency. Research indicates that the optimal potency is achieved when R is a nine-carbon chain (a nonyl group). OH r O D-R Mandelate esters (R = alkyl chain) Identify why nonyl mandelate is more potent than both octyl mandelate or decyl mandelate. Select all that apply. O Nonyl mandelate has a longer alkyl chain than octyl mandelate and is therefore less effective at penetrating cell membranes. Nonyl mandelate has a shorter alkyl chain than decyl mandelate, therefore it is more water-soluble. O Nonyl mandelate has a longer alkyl chain than octyl mandelate and is therefore more effective at penetrating cell membranes. O Nonyl mandelate has a shorter alkyl chain than decyl mandelate, therefore it is less water-soluble.
3. Use the priority system to draw the structure of the following molecule:2-methoxy-3-methyl-5-oxoheptanoic acid
NOC XT Ph CH₂ Both primary and secondary amines add to a ß-unsaturated aldehydes and ketones to yield ß-amino aldehydes and ketones rather than the alternative imines. Under typical reaction conditions, both direct and conjugate modes of addition occur rapidly. But because the reactions are reversible, they generally proceed with thermodynamic control rather than kinetic control so the more stable conjugate addition product is often obtained to the complete exclusion of the less stable direct addition product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H H CH3NH₂ CH3 H-A :A Ph NHCH3 вон CH3 :A H-A 8b
Which compound will decarboxylate (= loose CO2) most rapidly upon heating?
how the r-group affects the elimination, specifically E-1 reaction and how a different r-group would have a different effect
make use of the two images
Which of the following is the best representation of an aqueous lysine ? CH2 CH2 CH2 CH2 NH3 H,N-ÇH-COOH CH2 CH2 CH2 NH, H2N-CH-COO CH2 CH2 CH2 CH2 NH2 H2N-CH-COOH CH2 CH2 CH2 CH2 NH2
Draw the structure of two esters that will be reduced to propanol and butanol by LiAlH4 (followed by addition of aqueous acid).
CF 3- Celecoxib -SO2NH2 Do the following synthesis reactions. ŞO₂NH₂ NHNH2 A +