Answered: OH но. HO phthalic acid isophthalic…

Science

Chemistry

OH но. HO phthalic acid isophthalic acid pKa1 = 2.9 pK22 = 5.4 pKa1 = 3.7 pKa2 = 4.6

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

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.15P: In each pair, select the stronger acid. (a) Pyruvic acid (pKa 2.49) or lactic acid (pKa 3.08) (b)...

See similar textbooks

Related questions

Q: b. Hydrocyanic acid and methylamine (CH;NH;) c. Sulfurous acid (first proton only) and ethylamine…

A: b. When HCN and MeNH2 reacts together then salt MeNH3^+CN^- is formed. Molecular equation : HCN +…

Q: Phthalic acid and isophthalic acid have protons on two carboxy groupsthat can be removed with base.…

A: Normally acidic strength of a compound can be determined by the amount of stability of its conjugate…

Q: Squaric acid has a pKa of 1.5, making it much more acidic than many carboxylic acids (typical pKa…

Q: Define why are protons on an alpha carbon of an aldehyde or ketone more acidic than a proton on an…

A: When a base abstracts a proton from the alpha carbon atom of aldehydes or ketones, a carbanion is…

Q: Treatment of indene with NaNH2 forms its conjugate base in a Brønsted–Lowry acid–base reaction. Draw…

A: Since more the acidic nature of the molecule is lesser will be the pKa value And since the acidic…

Q: Which carboxylic compound of each pair would you expect to be stronger acid? Indicate (a) or (b) on…

A: In case 1) Me3N+ is an electron withdrawing group. It with draws electron from O-H bond through…

Q: The pKa of our product is ~ 2-3 units lower than the pKa of phenol. Draw all possible resonance…

A: Solution- All possible resonance structures of the conjugate base of the product given below-

Q: Identify the most and the least acidic compound in each of the following sets. Leave the remaining…

A: Acids are those substances with pH lesser than 7. They are able to donate hydrogen ions. There are…

Q: Why is acetamide a much weaker base than ammonia? Select one: a. The adjacent C-O makes the lone…

A: Since you have asked multiple questions, we will solve the first question for you. If you want any…

Q: Consider a triprotic acid whose most deprotonated form has a charge of -2. It's isoelectric point is…

A: The question is based on the concept of chemical equilibrium . We have to identify the pH range in…

Q: Treatment of indene with NaNH2 forms its conjugate base in a Brønsted–Lowry acid–base reaction. Draw…

Q: mention the conjugate bases and use structures to explain the following: a. why is the alpha proton…

Q: 3. Which one of the following answers represents the order of increasing bacisity for compounds the…

A: Arrange the following in increasing order of basicity : (1) CH3CH2ONa (2) (CH3)2NNa (3) CH3CO2Na…

Q: Two other commonly used sulfonic acids are methanesulfonic acid (CH3SO3H) and…

A: The given question contain incorrect spelling and formula (triuoromethanesulfonic acid (CH3SO3H)).…

Q: 7 NH2 2-aminopyridine 2-Aminopyridine has 2 nitrogens. Arrange the indicated nitrogens in decreasing…

A: We have to rank which nitrogen is more basic 1 or 7 and indicate nitrogen in decreasing order of…

Q: Explain why the a protons of an ester are less acidic than the a protons of a ketone by ~5 pkg…

A: The stronger acids have lesser value of pka and weaker acids have larger value of pka.

Q: The preceding equation for the protonation of acetamide shows a hypothetical product that is not…

A: The pKa represents the strength of an acid, which is calculated using acid dissociation constant…

Q: Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of…

A: pKa of acid : Ka is called the acid dissociation constant. If any compound easily gives H+ than the…

Q: 7 NH2 2-aminopyridine 2-Aminopyridine has 2 nitrogens. Arrange the indicated nitrogens in decreasing…

A: Basicity is the tendency to donate electron pair

Q: Which nitrogen in this molecule is the most basic? Explain briefly your choice (2) (3) If the…

A: On which N atom lone pair is localized, is more readily available for Lewis acids . Thus it is most…

Q: Although it was initially sold as a rat poison, warfarin is an effectiveanticoagulant used to…

A: The H-atom which is linked with 3o C-atom is considered as most acidic H-atom or proton. The…

Q: 2. Which carboxylic compound of each pair would you expect to be stronger acid? Indicate (a) or (b)…

A: The compound in which negative charge will be more stable will be more acidic in Nature. Hence…

Q: Why is acetamide a much weaker base than ammonia? Select one: a. The adjacent C-O makes the lone…

A: According to Lewis acid-base concept acids are electron pair acceptors due to vacant orbitals while…

Q: If compound A has a ka of 3.0 x 10-11 , compound B has a ka of 1.1 x 10-10 and compound C has a ka…

A: The modern method to express the strength of an acid or base is to measure the pKa value of the…

Q: Which proton in ketamine (C13H16ClNO) is the most acidic and what is the structure of its conjugate…

A: After removal of acidic proton, negative charge formed should should gets stabilized. Conjugate…

Q: Write an equation for the acid-base reaction between ethylmagnesium iodide and an alcohol. Use…

A: Grignard Reagent: When alkyl halides are reacted with magnesium in the presence of ethoxyethane or…

Q: Circle the compound with the lowest pK, and underline the compound with the highest pK. HO O,N.…

Q: Rank the following compounds in order of increasing acidity (1 = least acidic, 3 = most acidic) and…

A: The hydrogen atom present on the carbon atom adjacent to the carbonyl carbon is acidic in nature.…

Q: Somew 2. Consider the following compounds. NH

A: The compounds given are conjugate base of CH3COOH and CH3CONH2. So given anions are base.

Q: Phenol (pKa = 10.0) and benzoic acid (pKa = 4.2) both have acidic protons, although benzoic acid is…

Q: Rank the compounds in attached group in order of increasing acidity.

A: Carboxylic acids are acidic in nature due to the presence of -OH group attached to the carbonyl…

Q: Consider a triprotic acid whose most deprotonated form has a charge of -2. It's isoelectric point O…

Q: Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base.…

A: Normally acidic strength of a compound can be determined by the amount of stability of its conjugate…

Q: Thiocyanic acid (HSCN) is an inorganic acid (pKa = 1.1 at 25 °C) that can be classified as “strong”…

Q: Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base.…

A: Normally acidic strength of a compound can be determined by the amount of stability of its conjugate…

Q: With a pKa of 1.2, squaric acid is unusually acidic for a compound containing only C, H, and O. :ÖH…

A: Squaric is highly acidic in nature when there is removal of one proton takes Place then, the…

Q: Using the pk, table, estimate pK, values for the most acidic group on the compounds below, and draw…

Q: Arrange the following molecules in increasing order of acidity. Base it only on their structural…

A: We will draw structures of molecules and then decide order of acidic strength.

Q: Which carboxylic acid has the lower pKa, pyruvic acid (CH3COCO2H) or acetoacetic acid…

A: The acidity of a compound depends on the stability of the conjugate base. In pyruvic acid, adjacent…

Q: Histidine is an important catalytic residue found at the active sites of many enzymes. In many…

A: Histidine is the substituted alanine and is aromatic imidazole. This aromatic ring structure will be…

Q: Calculate the pH at25°C of a 0.65M solution of potassium acetate KCH3CO2. Note that acetic acid…

Q: The following three derivatives of succinimide are anticonvulsants that have found use in the…

A: Acidity of compound is mainly depending upon the Ka value or the acid dissociation constant.The…

Q: Although it was initially sold as a rat poison, warfarin is an effective anticoagulant used to…

Q: Which of the acids in the table above has the strongest conjugate base? Your answer Acidities of…

A: Lower the pKa value stronger the acid.

Q: The pka values of OH group in 4-cyanophenol and 4-nitrophenol are identical BUT in the…

Q: How would you describe the reaction between NaOH (a base) and the mixture of benzoic acid and methyl…

A: This is an example of acid base reaction between base NaOH and an acidic proton containing molecule…

Q: Solve the Attachment

A: Acids tend to lose H+ and form conjugate base. Stronger the acid, more is the Ka value and smaller…

Concept explainers

Amines

Amines are organic compounds with a nitrogen atom having a lone pair of electrons on it. They are derived from ammonia (NH3) wherein hydrogen atoms are substituted by an aryl or alkyl group.

Question

Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pK_a for loss of the first proton (pK_a1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pK_a for loss of the second proton (pK_a2) is higher for phthalic acid than isophthalic acid.

OH
но.
HO
phthalic acid
isophthalic acid
pKa1 = 2.9
pK22 = 5.4
pKa1 = 3.7
pKa2 = 4.6

Expert Solution

Step 1

Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base.

(a) Why the pK_a for loss of the first proton (pK_a1) is lower for phthalic acid than isophthalic acid has to be explained.

(b) Why the pK_a for loss of the second proton (pK_a2) is higher for phthalic acid than isophthalic acid has to be explained.

Step by step

Solved in 2 steps with 2 images

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Select the stronger acid in set given. Q.) Lactic acid (Ka 8.4 x 10-4) and ascorbic acid (Ka 7.9 x 10-5)
Rank the following in order of increasing pOH and justify: 0.10 M solutions of chloroacetic acid, carbonic acid, and citric acid Write out the order instead of placing 1, 2 ... Rank the following in order of increasing pKa and justify: 0.10 M mandelic acid, 0.20 M maleic acid, 0.40 M malonic acid. Write out the order instead of placing 1, 2 ...
Write TRUE if the statement is correct, FALSE if otherwis 42. The end point in the procedure of acid value is the disappearance of the pink color.43. Blank determination is employed in the determination of the Koettsdorfer number.44. Saponification is the alkaline hydrolysis of fatty oils which leads to formation of soaps.45. Esters are composed of carboxylic acids and alcohol.
Given that the Ka value for acetic acid is 1.8 × 10−5 and the Ka value for hypochlorousacid is 3.5 × 10−8, which is the stronger base, OCl− or C2H3O2−?
Benozic acid (C6H5COOH) has a pKa of 4.20. What is the ratio of the acid to its conjugate acid at a pH of 2.20 and what is the formula of the conjugate acid?
Using their Ka values, what is the pKb1 of 0.10 M chloroacetic acid 0.20 M carbonic acid 0.40 M citric acid
Which one of the following will be most acidic and why? 2-Chlorobutanoic acid, 4-Chlorobutanoic acid, Butanoic acid, 3-Chlorobutanoic acid
Which solution has the highest concentration of H3O+: a 0.50 M solution of acetic acid (CH3CO2H),or a0.50 Msolution offormic acid (HCO2H)? Ka of acetic acid is 1.8× 10−5 and Ka of formic acid is 1.8×10−4. Same Acetic acid Formic acid
1. Fumaric acid and malonic acid are both diprotic acids. a. Sketch the general shape of the curve for a diprotic acid with Ka1 >> Ka2. Explain how to determine pKa1, pKa2, and the molecular weight.b. Sketch the general shape of the curve for a diprotic acid with Ka1 ≈ Ka2.c. Sketch the general shape of a curve for a triprotic acid with Ka1 >> Ka2 >> Ka3.
If a diprotic acid, H2A, has a pK1 = 2.20 and pK2 = 9.31, what is the principal species of this compound at pH = 5.13? O H2A O A2- OHA O H3A+
Order the following acids with respect to increasing acidity: I. Fluoroacetic acid II. Chloroacetic acid III. 3-chloropropanoic acid IV. Propanoic acid
3. Rank the following acids in order from strongest to weakest.HA (pKa = 2.55) H2Z (pKa1 = 4.35) H3X (pKa1 = 3.17) HY (pKa = 5.72) 4. Rank each base in order from strongest to weakest.B (pKb = 4.12) Y– (pKa = 5.72 for conjugate acid) A– (pKa = 2.55 for conjugate acid)E (pKb = 8.12)