EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Chapter 22.7A, Problem 22.18P
Interpretation Introduction
Interpretation:
Mechanism for the aldol condensation of cyclohexanone is to be proposed. Whether the equiulibrium favor the reactant or the product is to be stated.
Concept introduction:
In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.
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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
base
H3C
H
OH
heat
H
+ H₂O
H
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.
In the mixed aldol reaction, the best results are obtained when one of the partners does not have an a-hydrogen. It cannot form an enolate anion and can therefore not undergo self-reaction. The
enolizable aldehyde is added slowly to a basic solution of the first aldehyde so that the mixed product is preferentially formed.
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.…
base
2
H3C
H
H3C
OH
heat
H
H3C
+ H₂O
H
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.
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 Instructions
X
:OH
H₂O:
а
کی
H₂C
H
H₂C
H
H
Chapter 22 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 22.2A - Prob. 22.2PCh. 22.4 - Without looking back, propose a mechanism for the...Ch. 22.4 - Prob. 22.8PCh. 22.4 - Prob. 22.9PCh. 22.5A - Prob. 22.10PCh. 22.5A - Prob. 22.11PCh. 22.5B - Prob. 22.12PCh. 22.5B - Predict the products of the following reactions....Ch. 22.5B - Which compounds will give positive iodoform tests?...Ch. 22.5C - Propose a mechanism for the acid-catalyzed...
Ch. 22.5C - Acid-catalyzed halogenation is synthetically...Ch. 22.6 - Show the products of the reactions of these...Ch. 22.7A - Prob. 22.18PCh. 22.7A - Prob. 22.19PCh. 22.7A - Prob. 22.20PCh. 22.7B - Prob. 22.21PCh. 22.8 - Prob. 22.22PCh. 22.8 - Prob. 22.24PCh. 22.9 - Prob. 22.25PCh. 22.9 - Prob. 22.26PCh. 22.9 - Prob. 22.27PCh. 22.9 - Prob. 22.28PCh. 22.9 - Prob. 22.29PCh. 22.10 - When cyclodecane-1,6-dione is treated with sodium...Ch. 22.11 - Prob. 22.32PCh. 22.11 - Prob. 22.33PCh. 22.12 - Prob. 22.34PCh. 22.12 - Prob. 22.35PCh. 22.12 - Prob. 22.36PCh. 22.12 - Prob. 22.37PCh. 22.12 - Show what esters would undergo Claisen...Ch. 22.13 - Prob. 22.39PCh. 22.13 - Prob. 22.40PCh. 22.14 - Prob. 22.41PCh. 22.14 - Prob. 22.42PCh. 22.14 - Show how crossed Claisen condensations could be...Ch. 22.14 - Prob. 22.44PCh. 22.14 - Prob. 22.45PCh. 22.15 - Prob. 22.46PCh. 22.16 - Prob. 22.47PCh. 22.16 - Prob. 22.48PCh. 22.17 - Prob. 22.49PCh. 22.17 - Prob. 22.50PCh. 22.17 - Prob. 22.51PCh. 22.18 - Prob. 22.52PCh. 22.18 - Prob. 22.53PCh. 22.18 - Prob. 22.54PCh. 22.18 - Prob. 22.55PCh. 22.18 - Prob. 22.56PCh. 22.19 - Prob. 22.57PCh. 22.19 - Prob. 22.58PCh. 22.19 - Prob. 22.59PCh. 22 - Prob. 22.60SPCh. 22 - 1. Rank the following compounds in order of...Ch. 22 - Prob. 22.62SPCh. 22 - Prob. 22.63SPCh. 22 - Prob. 22.64SPCh. 22 - Pentane-2,4-dione (acetylacetone) exists as a...Ch. 22 - a. Rank these compounds in order of increasing...Ch. 22 - Prob. 22.67SPCh. 22 - Prob. 22.68SPCh. 22 - 22-69 Predict the products of the following...Ch. 22 - Predict the products of these reaction sequences.Ch. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.72SPCh. 22 - Prob. 22.73SPCh. 22 - Prob. 22.74SPCh. 22 - The Knoevenagel condensation is a special case of...Ch. 22 - Prob. 22.76SPCh. 22 - Propose mechanisms for the following reactions.Ch. 22 - Prob. 22.78SPCh. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.80SPCh. 22 - Propose a mechanism for the following reaction....Ch. 22 - Prob. 22.83SPCh. 22 - Prob. 22.84SPCh. 22 - Prob. 22.85SP
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- Why is the Aldol reaction often called an Aldol condensation? 1) The initially formed b-hydroxy carbonyl compound loses an oxygen atom 2) The initially formed b-hydroxy carbonyl compound loses a hydrogen atom 3) The initially formed b-hydroxy carbonyl compound loses water 4) The initially formed b-hydroxy carbonyl compound loses a hydroxyl grouparrow_forwardWhat are the products of an aldol cyclization for the following compound?arrow_forwardI H H3C NOC XT :0: MET H₂C base 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. H OH q H3C H₂C 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 Instructions heat H H + H₂Oarrow_forward
- Consider the following reactions, and draw the products that are formed. Part 1 of 2 Draw the structure of the aldol addition product that results from dimerization of the following aldehyde. You do not need to show stereochemistry. H Part 2 of 2 NaOH Draw the structure of the aldol addition product that results from dimerization of the following aldehyde. You do not need to show stereochemistry. or H NaOHarrow_forward5. Propose a mechanism for the base-catalyzed hydrolysis of the nitrile. H₂O NaOH CEN 6. Propose a mechanism for aldol reaction. HiM Н н NaOH H₂Oarrow_forwardDraw a stepwise mechanism for the following variation of the aldol reaction, often called a nitro aldol reaction.arrow_forward
- What is the general name for the reaction product formed in an aldol addition reaction? O y-Hydroxy carbonyl compound a,B-Hydroxy carbonyl compound O a-Hydroxy carbonyl compound O B-Hydroxy carbonyl compoundarrow_forwardDrawing an Enol and a Ketone Formed by Hydration of an Alkyne Draw the enol intermediate and the ketone product formed in the following reaction.arrow_forwardDraw the structure of the major aldol product (prior to possible dehydration) of the following reaction. O ⇐ H dilute NaOH 95% aq. ethanol, 0-5° • You do not have to consider stereochemistry. •If no reaction occurs, draw the organic starting material. + HO CH3 On t ?arrow_forward
- Draw the two electrophiles for this reaction.arrow_forward2 Moin H3C H H₂C C⇒x= base :0: OH Hori H3C H. 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 B-hydroxy carbonyl compound. 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 Instructions H₂C Ἡ :0: heat H Home H3C + H₂Oarrow_forwardAldol condensation is a reversible reaction and in fact aldols can be transform into the starting carbonyl compounds. Complete using arrows, the following retroaldol reactionarrow_forward
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