Which step in the mechanism of the Aldol condensation reaction of a ketone is theone that makes the reaction irreversible?O Step 2 - attack of the nucleophilic enolate on a second equivalent of ketone toform a tetrahedral intermediateO Step 3 - protonation of the oxygen in the tetrahedral intermediate to form a beta-hydroxyketoneO Step 5 - loss of hydroxide through an E1cb eliminationO Step 1 - deprotonation of the ketone to form the enolateO Step 4 - deprotonation of the beta-hydroxyketone to form another enolate

Aldol condensation reaction is a reversible reaction. Here dilute base NaOH is used to form an…

Answered: Which step in the mechanism of the…

Which step in the mechanism of the Aldol condensation reaction of a ketone is the one that makes the reaction irreversible?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter26: Aldol And Claisen Reactions

Section: Chapter Questions

Problem 24E

See similar textbooks

Related questions

Q: Which is a reasonable intermediate in an aldol reaction of propanal? HO

A: Aldol reaction is a type of condensation reaction in which carbonyl compound having alpha H atom…

Q: Propose a mechanism for the aldol condensation of cyclohexanone. Do you expect theequilibrium to…

A: In base-catalyzed aldol condensation, nucleophilic addition of an enolate ion takes place on a…

Q: A different way of synthesising the product 4,4- diphenylbut-3-en-2-one is via an aldol…

A: aldol condensation is a condensation reaction in which an enolate ion reacts with a carbonyl…

Q: dibenzylacetone.

Q: please help Draw the mechanism for the synthesis (Include all the side products and possible…

A: Aldol condensation is a condensation reaction between two carbonyl compounds in which atleast one…

Q: The first step of the dimedone reaction involves an aldol reaction. Here is a simpler version -…

Q: for the theroretical yield is the mol correct? also using the aldol condensation reaction in this…

A: Aldol condensation is base catalysed condensation between two molecules of aldehyde or ketones. If…

Q: Complete the following base-catalyzed Self-Aldol Condensation reaction mechanism. Draw the structure…

A: Reactant is cyclohexanone. It has alpha hydrogens which in the presence of a base can be extracted…

Q: Provide all the possible porducts for the following Aldol reaction Он О Ph Ph Ph Ph но, д Ph Он О Ph…

Q: H.

Q: What starting materials are needed to synthesize each compound using an aldol or similar reaction?

A: Given compound,

Q: Write the structure for each aldol condensation product that is possible when a mixture of ethanal…

A: In aldol condensation, first enolate will generate. Here ethanal and propanal both can form enolate…

Q: The structures of two molecules, a B-keto ester and a B-unsaturated ketone, are given below.…

A: The reaction of two different types of esters in the presence of sodium alkoxide gives a beta-keto…

Q: If an aldol reaction does not use an acid to proceed, you might call it based catalyzed even, then…

A: Given: Base catalysed aldol condensation To find: Role of HCl in base catalysed aldol condensation…

Q: Draw the enolate anion and the ketone or aldehyde that would be needed to make this product through…

Q: Draw the products formed in the crossed aldol reaction of phenylacetaldehyde (C6H5CH2CHO) with each…

A: (a)Reaction of phenylacetaldehyde with CH2 (COOEt) 2 is shown in below

Q: Draw the reaction mechanism and predict the product of the aldol condensation between benzaldehyde…

A: Here we are required to draw the mechanism for aldol condensation reaction

Q: How many different products can be formed from a poorly planned crossed aldol addition with two…

A: In Aldol condensation : the enolate of carbonyl attack and get added to the carbonyl which on…

Q: 2. Draw the mechanism of the base-catalyzed aldol condensation reaction of two molecules of acetone…

Q: Draw the mechanism for the aldol addition reaction OH shown here, which is catalyzed by acid. Hint:…

Q: Which Syn product of this Aldol reaction would be favoured?

Q: Draw the two carbonyl compounds which could be used to make the enone shown below via the aldol…

A: Applying concept of Aldol reaction.

Q: one `H Benzaldehído Acetona Dibenzalacetona

Q: In an aldol condensation reaction, what is the difference if we use an ethanolic or aqueous NaOH…

Q: Formaldehyde does not take part in Aldol condensation. Why ?

A: Given Formaldehyde does not take part in Aldol condensation. Why ?

Q: 3. Draw the structure of all the expected aldol condensation products that will be formed by the…

Q: What is the product if this compound underwent aldol condesation with a base (NaOH), and how?

A: Answer

Q: Draw the structure of the major organic product of the following reaction. Predict whether the…

Q: Define Mechanism - The Intramolecular Aldol Reaction ?

A: Compounds containing two carbonyl underogoes intramolecular aldol reaction if a five or six-membered…

Q: What product would you expect to obtain from aldol cyclization of hexanedial, OHCCH2CH2CH2CH2CHO?

Q: Кон A Illi

A: ->Base can abstract most acidic hydrogen and form enolate ion which acts as nucleophile. -Now it…

Q: Which of the following statements describes the FIRST STEP in the mechanism of the aldol…

A: Ans

Q: Choose all the compounds that will be able to produce aldol condensation product from the reaction…

A: The aldehyde and ketones undergo a numerous reactions due to the acidic nature of alpha-hydrogen.…

Q: Choose all the compounds that will be able to produce aldol condensation product from the reaction…

A: Aldol condensation: It is type of condensation reaction in which enolate or enol reacts with…

Q: i need the mechanism for aldol condensation involving benzaldehyde and acetone

A: Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible…

Q: В. "GREEN CHEMISTRY": SOLVENT FREE ALDOL-CONDENSATION REACTION. i) Reaction H3CO NaOH H3CO H3CO OCH3

Q: Find one Aldol condensation reaction in acidic conditions and draw a step-by-step mechanism

A: Aldol condensation reaction is a reaction in which a ketone or aldehyde with alpha H present in them…

Q: NaOH + CH3 H3C `CH2CH3 `CH3 Ob. H3C CHCH3 H2C `CH2CH3 d. CH2

A: In a chemical reaction; the substance involves in conversion is said to be reactant whereas the…

Q: b) Step 2 of the aldol condensation OH NaOEt, ETOH H.

A: The aldol condensation reaction is the formation of β-hydroxyketone or β-hydroxyaldehyde (aldol…

Q: Based on the IR of the aldol product from the reaction, did the aldol condensation occur? How can…

A: Infrared spectroscopy (IR) is used for the identification of functional groups present in the…

Q: Show the two (neutral) organic starting materials that would be used to synthesize the following…

A: Carbonyl compounds are the compounds containing a C=O group. Aldehydes and ketones belong to…

Q: Consider the following crossed aldol condensation. Which statement explains why a single cross…

A: Given : reaction of cross aldol reaction. For aldol reaction there should be alpha hydrogen.

Q: For which of the following will the aldol reaction go the furthest toward completion?

Q: H. NAOH/H,0, heat

A: In an aldol condensation, an enolate ion reacts with a corbonyl compound in the presence of…

Q: Why is the enone product favored to be formed under the shown conditions rather than the aldol…

A: E1cB (Elimination Unimolecular Conjugate base) reaction involves the elimination of poor leaving…

Q: In an aldol condensation reaction where dibenzyl ketone is used to produce…

A: Aldol condensation is the reaction of aldehyde or ketone having alpha hydrogen atom with another…

Q: Define an aldol condensation ?

A: In Aldol Condensation, enolate ion (formed by aldehyde or ketone) reacts with another carbonyl…

Q: Show the mechanism of the given aldol reaction.

Q: Draw the aldol product for the reaction of the aldehyde shown with NaOH. Assume the reaction is run…

A: Welcome to bartleby !

Concept explainers

Organometallic Compounds

These are the compounds containing at least one carbon-metal bond in their molecule. It consists of metal and organic parts. These metals may be lithium, sodium, magnesium, zinc, and lead whereas the organic part can be the alkyl, aryl, alkenyl, or alkynyl group.

Question

Which step in the mechanism of the Aldol condensation reaction of a ketone is the
one that makes the reaction irreversible?
O Step 2 - attack of the nucleophilic enolate on a second equivalent of ketone to
form a tetrahedral intermediate
O Step 3 - protonation of the oxygen in the tetrahedral intermediate to form a beta-
hydroxyketone
O Step 5 - loss of hydroxide through an E1cb elimination
O Step 1 - deprotonation of the ketone to form the enolate
O Step 4 - deprotonation of the beta-hydroxyketone to form another enolate

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

Trending now

This is a popular solution!

Step by step

Solved in 2 steps

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Introduction to Organometallic Compounds

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

What is the first step in a base catalyzed aldol reaction? A. Protonation of Carbonyl group B. Elimination of Carbonyl with an alkene C. Formation of an Enolate D. Elimination of hydroxide E. Addition of nucleophile to R2C=O
Which statement describes why aldol reactions with ketones are low yielding? A.Ketones do not have acidic protons. B.Ketones are too electron poor at the carbonyl carbon. C.Ketones can attack other ketones well but perform poorly in self-condensations. D.The product of a ketone addition to a ketone has considerable steric strain.
In an aldol condensation reaction, acetone and benzaldehyde are mixed in the presence of sodium hydroxide to produce dibenzalacetone. Does it matter whether the acetone is added first to the aq. NaOH solution then the benzaldehyde, or if the benzaldehyde is added first to the aq. NaOH solution, then the acetone? Explain
The aldol double condensation reaction is highly selective for formation of a single double condensation product. Explain why only one aldol condensation product is formed despite two carbonyl compounds being present for the reaction.
3‑Methylbutanal undergoes an aldol reaction to form 3‑hydroxy‑2‑isopropyl‑5‑methylhexanal. Complete the mechanism for the reaction by adding missing atoms, bonds, charges, nonbonding electrons, and curved arrows
All are true or false a) The initially formed b-hydroxy carbonyl compound loses water in a Aldol condensation. b) Equilibrium favors the starting materials with both aldehydes and ketones for Aldol reactions. c)The Claisen reaction is a type of nucleophilic addition? d) The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product. e)b-Ketoester and an enolate are the two starting materials for a Robinson annulation
Using cyclopentanone as the reactant, show the product of a. acid-catalyzed keto–enol interconversion. b. an aldol addition. c. an aldol condensation.
What is the mechanism for this Aldol reaction?
Aldol Condensation What products are formed? What is the difference between aldol reactions and aldol condensation? What type of reaction condentionas are used?
Please complete the Aldol condensation reactions shown below
for the theroretical yield is the mol correct? also using the aldol condensation reaction in this portion are we using the aldol condensation reaction to synthesize acetophenone and para-methybenzaldehye. acetophenone 0.5 g, 4.2 mmol Para-methylbenzaldehyde 0.5 g, 4.2 mmol NaOH=0.18g = 4.5 mol Theroretical yield=0.93g =0.0519 mol Percent yield=76.8% Actual yield= 0.715 g Melting point observered= 93 degree Celsius Expected melting point =93-94.5 degree Celsius
What types of species are the electrophile and nucleophile in an aldol addition? 1. Nu: ester, E+: carbonyl 2. Nu: carbonyl, E+: carbonyl 3. Nu: carbonyl, E+: ester 4. Nu: ester, E+: ester