EtOnArrow-pushing InstructionsEtO.OEtEtO:H3C>XTOEt1. NaOEt, EtOH2. H3O+In the mixed Claisen condensation, the donor and target molecules are different. The target molecule is chosen as one thatdoes not contain an acidic a-carbon. The donor molecule, as in the case of the standard Claisen condensation, is one that hasmore than one acidic a-hydrogen. The mechanism for the mixed Claisen condensation proceeds as for the standard reaction:nucleophilic attack of the enolate anion on the carbonyl group of the target, expulsion of the weakest base, deprotonation todrive the equilibrium forward, and subsequent protonation to give the final product.Draw curved arrows to show the movement of electrons in this step of the mechanism.EtO.the fileOEtOEtH HHEtO.OOEt+EtOHEtOH OEt00H3CH3CH3CEsters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such assodium ethoxide, causes a reversible carbonyl condensation to occur that forms a ß-ketoester. This reaction is known as theClaisen condensation.XMwolpheH3CHOEtOEt1. NaOEt, EtOH2. H3O+The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a ß-ketoester. The steps leading up to this point are all reversible. The best yields for the Claisen condensation are obtainedwhen the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the a-carbon drivesthe reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount.Subsequent protonation with dilute aqueous acid results in high yield of the final product.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing Instructions+H-OH₂O:H3CΗ ΗOEt+OEtEtOHH₂O

We have been given two reactions and we have been asked to draw curved arrows in mechanism. Organic…

EtO. NA EtO. C OEt XT U U H3C OEt OEt In the mixed Claisen condensation, the donor and target molecules are different. The target molecule is chosen as one that does not contain an acidic a-carbon. The donor molecule, as in the case of the standard Claisen condensation, is one that has more than one acidic a-hydrogen. The mechanism for the mixed Claisen condensation proceeds as for the standard reaction: nucleophilic attack of the enolate anion on the carbonyl group of the target, expulsion of the weakest base, deprotonation to drive the equilibrium forward, and subsequent protonation to give the final product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 1. NaOEt, EtOH 2. H3O* EtO. EtO. C OEt OEt EtOH EtOH

EtO. NA EtO. C OEt XT U U H3C OEt OEt In the mixed Claisen condensation, the donor and target molecules are different. The target molecule is chosen as one that does not contain an acidic a-carbon. The donor molecule, as in the case of the standard Claisen condensation, is one that has more than one acidic a-hydrogen. The mechanism for the mixed Claisen condensation proceeds as for the standard reaction: nucleophilic attack of the enolate anion on the carbonyl group of the target, expulsion of the weakest base, deprotonation to drive the equilibrium forward, and subsequent protonation to give the final product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 1. NaOEt, EtOH 2. H3O* EtO. EtO. C OEt OEt EtOH EtOH

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

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.48AP: As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more...

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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

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EtO
n
Arrow-pushing Instructions
EtO.
OEt
EtO:
H3C
>XT
OEt
1. NaOEt, EtOH
2. H3O+
In the mixed Claisen condensation, the donor and target molecules are different. The target molecule is chosen as one that
does not contain an acidic a-carbon. The donor molecule, as in the case of the standard Claisen condensation, is one that has
more than one acidic a-hydrogen. The mechanism for the mixed Claisen condensation proceeds as for the standard reaction:
nucleophilic attack of the enolate anion on the carbonyl group of the target, expulsion of the weakest base, deprotonation to
drive the equilibrium forward, and subsequent protonation to give the final product.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
EtO.
the file
OEt
OEt
H H
H
EtO.
O
OEt
+
EtOH
EtOH

OEt
00
H3C
H3C
H3C
Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as
sodium ethoxide, causes a reversible carbonyl condensation to occur that forms a ß-ketoester. This reaction is known as the
Claisen condensation.
XM
wolphe
H3C
H
OEt
OEt
1. NaOEt, EtOH
2. H3O+
The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a ß-
ketoester. The steps leading up to this point are all reversible. The best yields for the Claisen condensation are obtained
when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the a-carbon drives
the reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount.
Subsequent protonation with dilute aqueous acid results in high yield of the final product.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
+
H-OH₂
O:
H3C
Η Η
OEt
+
OEt
EtOH
H₂O

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As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.
Answer true or false to the following statements about the mechanism of acid-base reactions. (a) The acid and base must encounter each other by a collision in order for the proton to transfer. (b) All collisions between acids and bases result in proton transfer. (c) During an acid-base reaction the lone pair on the base fills the A-H antibonding sigma orbital.
Complete a net ionic equation for each proton-transfer reaction using curved arrows to show the flow of electron pairs in each reaction. In addition, write Lewis structures for all starting materials and products. Label the original acid and its conjugate base; label the original base and its conjugate acid. If you are uncertain about which substance in each equation is the proton donor, refer to Table 4.1 for the relative strengths of proton acids. (a) NH3+HCl (b) CH3CH2O+HCl (c) HCO3+OH (d) CH3COO+NH4+
Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)
Several acids and their respective equilibrium constants are: Which is the strongest acid? Which is the weakest acid? Which acid has the weakest conjugate base? Which acid has the strongest conjugate base?
Label each molecule according to increasing acidity with 1 as the weakest and 4 as the strongest based on their structure. Explain.
Will this molecule be basic, acidic, both basic and acidic, or neither basic or acidic?
Rank the following compounds in order of increasing acidity, and explain your ranking. Br E A A COOH O₂N B COOH (least acidic) < с (most acidic) COOH The strongest acid has a strong electron-withdrawing group base. The weakest acid has a strong electron-donating group H₂C that will D B COOH destabilize that will stabilize the E .COOH Dositive D charge in its conjugate the negative charge in its A
1. Arrange the substances by order of acidity or basicity as indicated. You may use pKa tables and periodic tables. H F, OH, NH2, CH3CH2CH2CH2 Weakest Base Weakest Acid CH3CH2OH, CH3COOH, HF, Benzene Strongest Base @ NH H NH₂ H NH₂ Weakest Acid Strongest Acid NH₂ Strongest Acid
Can you please explain?
This ranking for the acidity of compounds confuses me. 1 = most acidic. I understand why the second compound is ranked first (it is more electronegative and a larger atom). However, I am struggling to apply the inductive effect to the rest of the compounds.
A ΝΗ most basic B > V с NH₂ V NH₂ H3CO E least basic NH₂