1. NaOEtCO₂Et2. H3O+3. heatBrH3CH₂CCO₂Et+CO₂HCO2+EtOHThe malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can bevisualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acidconditions, and decarboxylation.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsH:Ö:OHOHOHCO2БаCH3CH3

The malonic ester synthesis involves the formation of an enolate anion intermediate by reacting…

Answered: 1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter17: Alcohols And Phenols

Section17.SE: Something Extra

Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...

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An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.
Provide the reagents for the reactions.
shawl the detailed beland the neaction Label each спе of the reaction the ardor listed belanu. of part of the defalled mechanism wing of the terms listed.. - ester hydrolysis decarboxylaton Keto- endi tautomensin reaction. mechanism proceeds in •OCN3 OH 1130 + он '+' CH 3 CH + CO₂
5 a Copy and complete the two equations below, which can be used to show the alkylation and acylation of benzene, to produce the mono- substituted products. CH + CH,CH,CH,C — i ii C₂H₂ + CH₂CH₂CH₂CH₂COCI bi Name the mono-substituted organic product in partai. ii What class of compound is formed in part a ii?
Esterication is the reaction of a carboxylic acid (RCOOH) with an alcohol (R'OH) to form an ester (RCOOR') with loss of water. Equation [1] is an example of an intermolecular esterication reaction. Equation [2] is an example of an intramolecular esterication reaction; that is, the carboxylic acid and alcohol are contained in the same starting material, forming a cyclic ester as product. The equilibrium constants for both reactions are given. Explain why Keq is different for these two apparently similar reactions.
1. Provide the major organic products for the following reactions. NH NaBH/CH₂OH 1. LIAIH₂. Ether 2. H₂O* 1. n-ButylLi/Ether 2.NH, C
CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*
6. Write the structure of the organic product in each of the following reactions. Assume only monosubstitution for electrophilic aromatic substitution reactions. B HNO, acetic acid OH بلی NO₂ CI NO₂ Br₂ CHC NHANH, "OH CHÍNH, H₂SO
Give the major organic product(s) of the following reaction. 1) NABH4 ? 2) H3o+
The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents.
Explain why pentane-2,4-dione forms two different alkylation products (Aor B) when the number of equivalents of base is increased from one totwo.
Give the systematic (IUPAC) names for these molecules. Boononon cnolonongron. НаСНз CHОССH2СH2СНCHЗ CH3 phenyl propanoate |4-methyl pentane methanoat Incorrect. You mixed up the acyl and alkoxy portions of the molecule. Name the alkoxy part first, followed by the acyl part.

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