Please correct answer and don't used hand raiting Acetic acid (pKa 4.76) and trifluoroacetic acid (aka TFA; pKa 0.25) are similarin structure and both have carboxylic acid functional groups that make themacidic. What is the primary rationale for why trifluoroacetic acid has arelatively different acidity than the very similar structure of acetic acid?the overall molecule of acetic acid is bigger than TFAonly the acetic acid has a resonance structure that stabilizes its conjugate baseonly the TFA has a resonance structure that stabilizes its conjugate baseacetic acid has more inductive withdraw that stabilizes its conjugate base thandoes the TFATFA has more inductive withdraw that stabilizes its conjugate base than does theacetic acidTFA has less inductive withdraw that stabilizes its conjugate base than does theacetic acid

Acetic acid (top) and trifluoroacetic acid are both acidic due to their carboxylic group. The only…

Answered: Acetic acid (pKa 4.76) and…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 54AP

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The pka for 2-hydroxybenzoic acid (i.e. salicylic acid, used in pain relief and a precursor for aspirin) is 2.98, while the pKa for 3-hydroxybenzoic acid (found in castoreum, a scent- marking substance secreted by beavers) is 4.08. What does this difference in pK₂ tell us about the relative acidities of these two compounds?, Why is there such a significant difference? OH OH 2-hydroxybenzoic acid (pKa = 2.98) OH OH 3-hydroxybenzoic acid (pKa 4.08)
At pH 3.0, what percentage (in %) of lactic acid is in its deprotonated form? Hint: The pka of lactic acid is 3.86.
4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.
Acetic, formic, hydrofluoric, and acetylsalicylic acids have the following values of pKa (25°C), respectively: 4.74, 3.74, 3.17, 3.49. Order these acids in order acidity (from highest to lowest acidity)
Draw the structure of chloric and chlorous acid and predict their pKa values using Pauling's rules.
но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.
Sulfuric acid (H2SO4) has a pKa value of -10 and it is almost completely ionized in water. Write the ewis structure for the conjugate base of sulfuric acid. Draw all the possible resonance structures for the corresponding conjugate base.
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Suppose you have a mixture of these three compounds. Devise a chemical procedure based on their relative acidity or basicity to separate and isolate each in pure form.
The pkb of methylamine, CH3NH2, is 3.36. Calculate the pka of its conjugate acid, CH3NH3*. pka =
Explain the following 1. difference between pka1 and pka2 for carboxylic acids of the type HOOC(CH2)COOH decreases as n increases 2. Arrange oxalic,manolic,succinic, and glutanic acids in order of activity( first ionisation). How do you account for this order?
The C-H bond in acetone, (CH,),C=0, has a pk, of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH,CH,CH, (pK,= 50). Use skeletal structures for the resonance structures. Resonance structures: draw structure draw structure (negative charge on C) (negative charge on O) Acetone is much more acidic than propane because: Acetone's conjugate base has fewer resonance structures than propane's conjugate base. The negative charge on acetone's conjugate base is stabilized by resonance. The negative charge on acetone's conjugate base is stabilized by inductance, Acetone's higher molecular mass makes it more acidic than propane.

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