Write the complete stepwise mechanism for the acid-catalyzed hydrolysis of the following amide to yieldmandelic acid. Show all electron flow with arrows and draw the structures of all intermediate species.OHH-OH₂CnH2:0:OHC OH + NH410:The purpose of the acid catalyst in the hydrolysis of an amide is:to enhance the electrophilicity of the amide carbonyl carbona.to enhance the nucleophilicity of the water moleculeb.C.to enhance the electrophilicity of the water moleculed.to shift the equilibrium of the reaction

The reaction shown is the hydrolysis of an amide to form a carboxylic acid. With primary amides,…

Answered: Write the complete stepwise mechanism…

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

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.59P

See similar textbooks

Similar questions

On the basis of the general mechanism for amide hydrolysis in acidic solution shown in Mechanism 20.4, write an analogous sequence of steps for the hydrolysis of acetanilide.
need help with chemistry reactions questions
Amoxycillin is often adminisstered as the sodium salt. It is more soluble form that results from the reaction: Amoxycillin + NaOH --> Sodium-amoxycillin + H2O What functional grouo omn amoxycillin allows it to act as an acid in the reaction?
Reactions of Carboxylic Acids - Fisher esterification: Acid-catalyzed ester formation from carboxylic acid and alcohol OH H₂SO4 OH - Carboxylic acid: conversion to acyl halides: SOCI₂ RCO₂H + SOCI₂ (w/ pyridine) → RCOCI SOCI₂ CH3OH CH3COH Reactions of Amide NH₂ 1. LiAlH4 2. H₂O
H3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br Br
Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.
Primary amines can be converted into secondary amines by reaction with haloalkanes. This reaction is difficult to achieve in the lab because of the large number of byproducts. Select the possible products or byproducts of the reaction. H3C-NH2 The products and `Br byproducts are: (1 equiv) (1 equiv) O B D Bre HN CH, O I E A B D F Br H Br O O K E O Br O OG O A J K O O O O O O O O
7. Amines (R-NH2, R₂NH, or R³N) are the organic analogs of ammonia (NH3) where one or more of the hydrogens on the nitrogen has been replaced by an alkyl group (R). Like ammonia, amines are basic with pKb's in the same range as the pka's of carboxylic acids. Amines readily form their water soluble conjugate acids in the presence of 5% aqueous HC1. Work out an extraction procedure to separate the following compounds. I CI CO2H CI NH₂ crystais lea liquor and is General Process for Recrystallization: 84 CI boiling (bot) solvem ough flated filter pap then cool in ice-bath CH 3 neutral
Please don't provide handwritten solution.
H3C- H3C. OH XT H Et H2N–CH2CH3 It is difficult to prepare an amide from a carboxylic acid and an amine directly, since an acid-base reaction occurs which renders the amine nitrogen non-nucleophilic. Typically, in such an amide synthesis, the carboxylic acid OH group is first transformed into a better, nonacidic leaving group. In practice, amides are often prepared by treating the carboxylic acid with dicyclohexylcarbodiimide (DCC). The amine is then added and nucleophilic acyl substitution occurs easily because dicyclohexylurea is a good leaving group. This method of amide bond formation is a key step in the laboratory synthesis of peptide bonds (amide bonds) between protected amino acids. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions +N. H DCC alb :A alo H3C H3C CH₂CH3 Et H-A
The reaction between propanoic acid and benzyl alcohol in an acidic medium. Show the product by writing the reaction together with its mechanism.
a. The carbonyl group of an amide is less reactive towards nucleophilic substitution reactions because of the so-called amide resonance interaction of nitrogen lone pair (RC=ONR’2 → RC- O=NR2). (Relative reactivities of carbonyl compounds, increasing reactivity: nitriles < amides < esters, acids << ketones < aldehydes < acid chlorides.) However, the amides formed from imidazole (N- acylimidazoles) are highly reactive, and can be used to deliver acyl groups in much the same way as "active" esters, acid anhydrides and acid chlorides. An advantage to using N-acylimidazoles is that the imidazole that is released serves a base so additional base does not need to be added. Imidazole amides have been used in peptide and nucleoside chemistry to attach -amino acid residues to alcohols and amines. Using N-propanoylimidazole and N,N-dimethylpropanamide as examples explain why the imidazole amide is a good acylating agent. b. The amide functional group is one of the more stable carbonyl containing…

SEE MORE QUESTIONS

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry: A Guided Inquiry

Chemistry

ISBN:

9780618974122

Author:

Andrei Straumanis

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry: A Guided Inquiry

Chemistry

ISBN:

9780618974122

Author:

Andrei Straumanis

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS