compound, forming an enolate ion. The enolate ion has two resonance contributors. In the box on the right, draw the best esonance structure of the enolate ion on the left. Draw electron-flow arrows on the structure on the left to indicate how the electrons reorganize to give the structure on the right. H,C CH Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron-flow arrows should start on the electron(s) of an atom or a bond and should end on an atom, bond, or location where a new bond should be created.

compound, forming an enolate ion. The enolate ion has two resonance contributors. In the box on the right, draw the best esonance structure of the enolate ion on the left. Draw electron-flow arrows on the structure on the left to indicate how the electrons reorganize to give the structure on the right. H,C CH Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. Electron-flow arrows should start on the electron(s) of an atom or a bond and should end on an atom, bond, or location where a new bond should be created.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter24: Carboxylic Acids & Derivatives

Section: Chapter Questions

Problem 9E

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Similar questions

Can you select the answers in each bracket? The imine functionality is similar to [ carbonyl / nucleophile / acid / amine] meaning that it can react as [ electrophile / nucleophile / proton acceptor / proton donor ] if paired with [ electrophile / nucleophile / acid / base ] . Similarly to, [ carbonyls / enols / alkenes/ bases ], enamines will undergo alpha substitutions when paired with [ electrophile / nucleophile / acid / base ] .
The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael addition) reaction as shown below: a) Propose a mechanism for the reaction starting from the enolate shown below. You can assume water is present for any proton transfers needed.b) We saw that the keto tautomer is normally preferred over the enol tautomer, however, the enol tautomer is present in the final product (Warfarin) and that is the more stable tautomer in this case. Why do you think the enol tautomer is more stable? Hint: consider the molecule as a whole.
Except for the Tollens test, basic aqueous conditions are generally avoided with sugarsbecause they lead to fast isomerizations.(a) Under basic conditions, the proton alpha to the aldehyde (or ketone) carbonylgroup is reversibly removed, and the resulting enolate ion is no longer asymmetric.Reprotonation can occur on either face of the enolate, giving either the original structureor its epimer. Because a mixture of epimers results, this process is called epimerization.Propose a mechanism for the base-catalyzed equilibration of glucose to a mixture ofglucose and its C2 epimer, mannose.*(b) Propose a mechanism for the isomerization of a ketose to an aldose, via the enediolintermediate, shown immediately above. Note that the enediol has two ¬OH protons,and removing one or the other gives two different enolate ions.
A)There are two plausible enolates that can arise when LDA is used as the base for the ketone shown. In each statement circle what best describes the enolate? The enolate is formed under either a) irreversible or b) reversible conditions The favored is either the a) more stable or b) less stable enolate The favored enolate is either the a) kinetic or the b) thermodynamic enolate B) What is the major enolate? (structure)
Enolates are formed by deprotonation of an α-carbon hydrogen. Answer the following questions about enolate formation. In the molecule shown, select the α-carbon hydrogen that would be removed to form an enolate when NaOEt is used as a base. Draw the thermodynamic enolate that results for the molecule in Part 1. Draw only the enolate resonance form that includes a formal charge on the α carbon. Be sure to indicate that formal charge as well as any lone pair of electrons in your answer.
The product in this reaction is basic enough to be protonated by a dilute HCl solution. Draw the protonated species, clearly showing where protonation occurs. Draw all possible resonance structures of the conjugate acid of the product, and use these to explain why the product is so much more basic than a typical ester, like ethyl acetate.
This is Wittig Rxn: Whatever mechanism you choose to draw is fine since you can leave the base as B: Draw the arrow pushing mechanism using the compounds below – Constant: 4-nitrobenzyl benzaldehydebase 1: triethylaminebase 2: NaOHbase 3: K2CO3ylide: Acetonyltriphenylphosphonium chloride
1. Discuss the role of the Aldol condensation reaction in the synthesis below. What specific reaction was used in the synthesis? What is the importance of the aldol reaction in the entire synthetic approach? 2. Show the detailed reaction mechanism involved in their corresponding specific parts in this syntheses.
1. Provide the mechanism of the reaction shown in the picture. 2. Explain why it cannot be done in basic conditions. 3. Why is the enol tautomer favored over the keto tautomer?
Rank these substrates in order of increasing ability to undergo a nucleophilic substitution aromatic (SNAr) reaction.
LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?
Show the process of synthesizing an enolate compound from cyclohexanone using an LDA catalyst.