Show the resonance forms for the enolate ions that result when the following compoundsare treated with a strong base.(a) ethyl acetoacetate (b) pentane-2,4-dione(c) ethyl a@cyanoacetate (d) nitroacetone

Show the resonance forms for the enolate ions that result when the following compoundsare treated with a strong base.(a) ethyl acetoacetate (b) pentane-2,4-dione(c) ethyl a@cyanoacetate (d) nitroacetone

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

Chapter17: Carboxylic Acids

Section17.9: Decarboxylation

Problem 17.6P

See similar textbooks

Related questions

Q: The intramolecular aldol reaction of 6-oxoheptanal [CH3CO(CH2)4CHO] can yield three cyclic…

Q: 1-Propose a reasonable biosynthesis of B-eudesmol from Farnesylpyrophosphate B-Eudesmol

Q: (2R, 3S) -3-phenylbutan-2-ol tosylate undergoes E2 removal when treated with sodium ethoxide. Draw…

A: Note : In E2 elimination OTs, H and ethoxide ion in one plane (anti periplanar transition state)…

Q: The formula for the alarm pheromone for one species of ant is C7 H7 O. When treated with I2 and…

A: Given information, Pheromone yields iodoform and n-hexanoic acid with I2 and NaOH,

Q: Jiadifenin is a natural product isolated from the fruit of the Chinese plant Illicium jiadifengpi,…

A: A stepwise mechanism for the conversion of M to N has to be drawn.

Q: When N-bromosuccinimide is added to hex-1-ene in CCl4 and a sunlamp is shone on themixture, three…

Q: b) When 2,5-dimethytfuran (1) is boled with concentrated HCI, a połymer is formed. 13 molecules of…

Q: 4. Give a detailed mechanism for a reaction of ethylamine and acetyl chloride under basic…

Q: From what aldehyde or ketone could each of the following be prepared by reduction with NaBH4 or…

Q: 4. Write the principal products of the reactions of the following compound with excess of the…

Q: Give a rearrangement reaction equation to synthesize N-ethyl-2-methyl-buthylamide from the…

Q: please help with this question. thank you. Provide a detailed, stepwise mechanism for the…

Q: 3. The major organic product which results when PHCHO is treated with the following sequence of…

A: From given Both the question is solved according Initially the sequence is given and schiff base…

Q: Predict the products obtained from the reaction of oleic acid with the following reagents (i) Excess…

A: The structure and the molecular formula of oleic acid are as follows:

Q: Draw the structure of the product/s in each of the following reactions. Ethanoyl chloride (A) Acetic…

Q: Give the structure of the product formed on reaction of ethyl acetoacetate with each of the…

A: (a) 1-Bromopentane and sodium ethoxide (b) Saponification (basic hydrolysis) and decarboxylation of…

Q: Write the complete stepwise mechanism for the acid-catalyzed hydrolysis of the following amide to…

Q: Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally…

A: Given reaction,

Q: H. (a) (b)

A: Aldol condensation reaction - two moles of aldehyde (or ketone) in presence of strong base react…

Q: А. В. С. Which of this/these compound/s will not undergo acid-catalyzed hydrolysis? Compound D is:…

A: Names of the given compounds are: A - Cyclohexanone B - δ-Valerolactone C -…

Q: Which of the following best represents a mechanistic step in the acid-catalyzed hydrolysis of…

Q: Give the expected organic product when phenylacetic acid, PhCH2COOH, is treated with reagent…

Q: Give the structure of compounds A to E in the following reaction sequence.

Q: Oc-OH Which of the following can be hydrolyzed with acid to give benzoic acid, NO2 CN HN-NH2 OCCH,…

Q: Provide a detailed, stepwise mechanism for the acid-catalyzed formation of acetophenone dipropyl…

A: When ketone reacts with alcohol first it form hemiketal and then this hemiketal further react with…

Q: Suggest a synthesis of the following compound by Claisen or Dieckmann condensations. Show all…

Q: Give the expected organic product when phenylacetic acid, PhCH2COOH, is treated with reagent…

A: When carboxylic acid reacts with sodium hydroxide there will be a formation of sodium salt of that…

Q: a) Ketoacid Z below can be synthesized from ethyl acetoacetate W via an acetoacetic ester synthesis.…

Q: cyclopentanone react with hydroɡen cyanide. Predict the product of this reaction!

Q: Question 1 Compound A below undergoes Dieckmann cyclization to give compound B, in the presence of a…

A: Carbonyl containing carbon atom is electrophilic in nature because of the electron accepting…

Q: Show the resonance forms for the enolate ions that result when the following compoundsare treated…

A: c) The alpha hydrogen of ethylcyanoacetate is deprotonated by ethoxide ion to give enolate ion. The…

Q: What product will be obtained from 2,3-Diphenylbutane-2,3-diol on heating it in an acidic medium…

A: Structure of 2,3‐Diphenylbutane -2,3-diol is Which has (-OH) functional groups.

Q: b) OH Hemiacetal H3C D Compound D could be converted into a cyclic hemiacetal in the presence of an…

A: Aldehydes on treatment with an alcohol in the presence of an acid produces hemiacetal.

Q: 1. Draw the retrosynthetic analysis of compound A by providing the appropriate disconnection and…

A: We have to suggest a complete synthetic pathway with the reagents and reaction conditions to…

Q: If a 1:1 mixture of ethyl ethanoate and methyl butanoate is treated with base under Claisen…

A: When two ester undergoes condensation reaction is presence of base to give beta keto ester, the…

Q: From what aldehyde or ketone could each of the following be prepared by reduction with NaBH4 or…

A: Lithium borohydride (LiBH4) is a stronger reducing agent than sodium borohydride (NaBH4), But both…

Q: (a) Write a suitable chemical equation to complete each of the following transformations :(i)…

A: We are authorized to answer one question at a time, since you have not mentioned which question you…

Q: The Favorskiireaction involves treatment of an a-bromo ketone with base to yield a ring-contracted…

Q: In 1887, the Russian chemist Sergei Reformatsky at the University of Kiev dis- covered that…

A: Reformatsky reaction is type of organic reaction in which the condensation of an aldehyde or…

Q: Proline betaine is a putative osmoprotectant in plants and bacteria, helping to prevent dehydration…

A: Given compound:

Q: Draw the structures of the nucleophilic B-keto ester and the aB-unsaturated ketone acceptor that…

A: The retrosynthesis of the given compound gives us the nucleophilic beta-keto ester and alpha-beta…

Q: 2-Ethyl-1-hexanol was needed for the synthesis of the sunscreen octyl p-methylcinnamate. Show how…

A: (a) Addition reaction of ketones and aldehydes is an aldol reaction and it is reversible reaction.…

Q: Use your knowledge of carbonyl chemistry and reaction mechanisms to explain the following biological…

A: Carbonyl group is an organic functional group which is composed of a carbon atom to doubly bonded…

Q: Give the expected products of lithium aluminum hydride reduction of the followingcompounds (followed…

A: ANSWER: Step 1: (a). Butyronitrile on reducing with lithium aluminum hydride followed by hydrolysis…

Q: Osary to synthenize thie compound by mthesis teps neceossary to synthesize this compound bya kyl…

A: Given (A) CH3COOCH2CH2CH3 (B) HOCH2CH2CH2CH3 (C) CH3CH2CH2OCH2CH2CH3 (D) CH3CH2CH2CH2CHO We have to…

Q: Which of these molecules will cyclize to give the insect pheromone frontalin? OH Но HO Frontalin (A)…

Q: Predict the product of the reaction of p-methylbenzoic acid with each of the following: (a) LiAlH4,…

Question

Show the resonance forms for the enolate ions that result when the following compounds
are treated with a strong base.
(a) ethyl acetoacetate (b) pentane-2,4-dione
(c) ethyl a@cyanoacetate (d) nitroacetone

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Step 3

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 3 steps with 3 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?
Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.
Provide a mechanism for the following isomerization in aqueous acid. Thank you in advance!
Acetone reacts with carbohydrates in the presence of an acid catalyst to form products that are commonly referred to as “isopropylidene” or “acetonide” derivatives. The carbohydrate d-ribono-(1,4)-lactone reacts with acetone in the presence of hydrochloric acid to give the acetonide shown here. Write a mechanism for this reaction.
Give a rearrangement reaction equation to synthesize N-ethyl-2-methyl-buthylamide from the corresponding α-diazoketone. Give the structures of all intermediary products. Do not give a mechanism.
When phenylacetaldehyde (C6H5CH2CHO) is dissolved in D2O with added DCl, the hydrogen atoms a to the carbonyl are gradually replaced by deuterium atoms. Write a mechanism for this process that involves enols as intermediates.
The Favorskiireaction involves treatment of an a-bromo ketone with base to yield a ring-contracted product. For example, reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid.what is the mechanism of the reaction.
The following scheme shows the retrosynthetic analysis of 1-isopentylaziridine to form series of intermediates via Functional Group Inversion (FGI). Choose the correct reagents of N-S for the respective conversion
(a) Write a suitable chemical equation to complete each of the following transformations :(i) Butan-l-ol to butanoic acid(it) 4-Methylacetophenone to benzene-1, 4-dicarboxylic acid(b) An organic compound with molecular formula C9H10O forms 2, 4-DNP derivative, reduces Tollen’sreagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1, 2-benzenedicarboxylic acid. Identify the compound.
a. Provide the structure of the hydrate of cyclopentanone. b. Provide the major organic product which results when pentanal is subjected to the following sequence of steps: 1. PhMgBr; 2. H3O+; 3. PCC.
a) Write out the first 3 steps only(to the tetrahedral intermediate shown) in the 6-step arrow pushing mechanism showing how ethyl propanoate is hydrolyzed in acid to form propanoic acidand ethanol. b) NaOH/H2O also serveto hydrolyze an ester; briefly explain why NaOH/H2Ois generally preferable.
When N-bromosuccinimide is added to hex-1-ene in CCl4 and a sunlamp is shone on themixture, three products result.(a) Give the structures of these three products.(b) Propose a mechanism that accounts for the formation of these three products