Answered: Predict the products of reactions of…

Predict the products of reactions of carboxylic acids with alcohols, amines, diazomethane,reducing agents, and organometallic reagents, and give mechanisms where appropriate

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 41MP: Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to...

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Question

Predict the products of reactions of carboxylic acids with alcohols, amines, diazomethane,
reducing agents, and organometallic reagents, and give mechanisms where appropriate

Definition Definition Organic compounds with a nitrogen atom having a lone pair of electrons on it. Amines are derived from ammonia (NH 3 ), wherein hydrogen atoms are substituted by an aryl or alkyl group.

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Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.
Predict the products and propose mechanisms for the reactions of ketones and aldehydes with oxidizing and reducing agents, amines, alcohols, and phosphorus ylides.
(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.
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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:
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) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enal
Please provide a step by step list explaining the mechanism for the reactions
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Rank the following carboxylic acids derivatives based on their reactivity towards nucleophiles (1-most reactive - 4- least reactive), and describe the structural features you use to detrmine your ranking.
Give an explanation, why the acidity of these phenolic derivatives give these pKa value? Describe it by using the electronic effect on the acidity.
Write the formula of reagents used in the following reactions:(i) Bromination of phenol to 2,4,6-tribromophenol(ii) Hydroboration of propene and then oxidation to propanol.(b) Arrange the following compound groups in the increasing order of their property indicated:(i) p-nitrophenol, ethanol, phenol (acidic character)(ii) Propanol, Propane, Propanal (boiling point)