When a methyl ester is hydrolyzed under acidicconditions in H,180, the 180 isotope ends up in thecarboxylic acid. When a tert-butyl ester is hydrolyzedunder the same conditions, the labeled oxygen endsup in the alcohol product. (a) Propose mechanisms toaccount for these observations. (b) Explain why eachester undergoes the respective mechanism.CH3+ Но-СНЗ18+ H180HОН

To Find: To find the mechanism involved in the given reaction and explain why each ester undergoes…

Answered: When a methyl ester is hydrolyzed under…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 62AP

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Please give the main substitution product for each of the following reactions, and indicate the dominant mechanism: (a) 1-bromopropane + NaOCH3 → (b) 3-bromo-3-methylpentane + NaOC2H5 →
When 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of substitution and elimination products is obtained. Provide structures for all possible products, writing [not drawing] the name of the mechanism by which each one is formed.
Explain the mechanism of the following reactions :(i) Addition of Grignard’s reagent to the carbonyl group of a compound forming an adduct followed by hydrolysis.(ii) Acid catalysed dehydration of an alcohol forming an alkene.(iii) Acid catalysed hydration of an alkene forming an alcohol.
c) An alkyl halide E, C5H11B1 undergoes hydrolysis to form an alcohol F, C5H120. Alcohol F becomes cloudy immediately when reacted with a Lucas reagent. (i) (ii) Deduce the structures of E and F. State the type of reaction and propose the mechanism for the conversion of E to F. d) Draw the structure of the product formed when 2-bromopropane reacts with the following reagents respectively, (i) (ii) potassium cyanide ethoxide ion
SN1 substitution and E1 elimination frequently compete in the same reaction.(a) Propose a mechanism and predict the products for the solvolysis of2-bromo-2,3,3-trimethylbutane in methanol
2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (ii) What is the type of reaction involved in the formation of compound W? (iii) Identify the major product of the elimination reaction between compound Xand compound Y based on Zaitsev’s rule.
(S)-3-methylpentan-2-one.(b) When cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing atrace of NaOH, a mixture of cis and trans isomers results. Propose a mechanism forthis isomerization.
Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.
When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.
Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:
A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:

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