The compound shown below is the product of a Claisen condensation or a Dieckmann condensation. Draw structural formulas for the ester and enolate ion reactants. Remember that a Dieckmanncondensation is intramolecular and therefore the enolate ion and the ester are part of the same reactant.LDraw the enolate ion in its carbanion form.Assume all esters to be used are ethyl esters.Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.⚫ Separate multiple reactants using the + sign from the drop-down menu.+n?ChemDoodleда

See the explanation box.Explanation:

Answered: The compound shown below is the product…

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

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.9P

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The compound shown below is the product of a Claisen condensation or a Dieckmann condensation. Draw structural formulas for the ester and enolate ion reactants. Remember that a Dieckmann condensation is intramolecular and therefore the enolate ion and the ester are part of the same reactant. • Draw the enolate ion in its carbanion form. • Assume all esters to be used are ethyl esters. • Draw one structure per sketcher. Add additional sketchers using the drop- down menu in the bottom right corner. Separate multiple reactants using the + sign from the drop-down menu.
The compound shown below is the product of a Claisen condensation or a Dieckmann condensation. Draw structural formulas for the ester and enolate ion reactants. Remember that a Dieckmann condensation is intramolecular and therefore the enolate ion and the ester are part of the same reactant. e Draw the enolate ion in its carbanion form. • Assume all esters to be used are ethyl esters. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple reactants using the + sign from the drop-down menu. ChemDoodle 86 b
The compound shown below is the product of a Claisen condensation or a Dieckmann condensation. Draw structural formulas for the ester and enolate ion reactants. Remember that a Dieckmann condensation is intramolecular and therefore the enolate ion and the ester are part of the same reactant. • Draw the enolate ion in its carbanion form. • Assume all esters to be used are ethyl esters. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple reactants using the + sign from the drop-down menu. • 0▾
describe how steric and electronic effects influence the postion of equilibrium when the electrophilic center of an aldehyde or ketone is under nucleophilic attack.
What explains why many aldehydes and ketones can undergo self-condensation reactions in basic conditions? The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon is an electrophile. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile. The oxygen of the carbonyl group can attack the carbon of the carbonyl group. Only esters can undergo self-condensation reactions.
An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of reaction is this? an acid-catalyzed aldol condensation a Fischer esterification. a Grignard reaction. a base-mediated aldol condensation
Which is the oxaphosphetane intermediate? Br Ph3P-CH,CH,Ph NaH THF Ph3P-CHCH,Ph Reaction intermediate C14H18 ketone ylide
Crossed Claisen condensation reactions require: 1) Two esters where only one can form an enolate anion. 2) Two esters where both can form enolate anions. 3) Two esters where neither can form an enolate anion. 4) The ability to undergo intramolecular reactions. O 1 O 2 4
The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an a-bromo ester with zinc. +ZnBr ОН CH;CH CH,CH,CHCH .C OCH3 CH;CH,CHCH .C OCH3 OCH3 Но CH3CH CH3 ZnBr organozinc reagent ČH3 B-hydroxy ester Describe how each of the following compounds can be prepared, using a Reformatsky reaction: ОН ОН ОН C. ОН .C. a. CH;CH,CH,CHCH b. CH3CH,CHCH CH,CH3 OCH3 с. СН-СH-CH—С ОН d. CH3CH2CCH OCH3 CH3 CH,CH3
this drug contains one or more building blocks derived from either ethylene oxide or epichlorohydrin.Identify the part of each molecule that can be derived from one or the other of the building block and propose structural formulas for the nucleophile(s) that can be used along with either ethylene oxide or epichlorohydrin to synthesize each molecule.
A strong acid is generally used to catalyze the Fischer esterification of carboxylic acids.What two steps in the reaction are accelerated by the presence of strong acid? What function does the acid play in each of these steps?
2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O H

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