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Bromoacetic Acid Pka

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Deciphering the pKa of Bromoacetic Acid: A Comprehensive Exploration



Bromoacetic acid, a simple halogenated carboxylic acid, serves as a valuable model compound for understanding the influence of substituents on acidity. This article aims to provide a comprehensive understanding of its pKa value, exploring the factors that contribute to its acidity and its implications in various chemical contexts. We will delve into the definition of pKa, examine the structural features of bromoacetic acid influencing its acidity, and discuss its applications.

Understanding pKa: A Measure of Acidity



The pKa value is a quantitative measure of the strength of an acid. It represents the negative logarithm (base 10) of the acid dissociation constant (Ka). A lower pKa value signifies a stronger acid, indicating a greater tendency to donate a proton (H⁺) in aqueous solution. The dissociation of a generic acid, HA, can be represented as:

HA ⇌ H⁺ + A⁻

The Ka is defined as:

Ka = [H⁺][A⁻] / [HA]

where [H⁺], [A⁻], and [HA] represent the equilibrium concentrations of the proton, conjugate base, and undissociated acid, respectively. Therefore, pKa = -log₁₀(Ka).

The Structure and Acidity of Bromoacetic Acid



Bromoacetic acid (CH₂BrCOOH) differs from acetic acid (CH₃COOH) by the substitution of a hydrogen atom with a bromine atom on the α-carbon (the carbon atom adjacent to the carboxyl group). This seemingly minor change has a significant impact on the molecule's acidity.

The increased acidity of bromoacetic acid compared to acetic acid (pKa of acetic acid is approximately 4.76, while bromoacetic acid's pKa is approximately 2.69) can be attributed to the electron-withdrawing inductive effect of the bromine atom. Bromine is more electronegative than hydrogen; therefore, it pulls electron density away from the carboxyl group. This electron withdrawal stabilizes the conjugate base (bromoacetate ion, CH₂BrCOO⁻) by dispersing the negative charge more effectively. A more stable conjugate base leads to a greater extent of dissociation and thus, a lower pKa value.

This inductive effect is also distance-dependent. The closer the electron-withdrawing group is to the carboxyl group, the stronger its effect on the acidity. For instance, if the bromine atom were further away from the carboxyl group, the inductive effect would be weaker, and the pKa value would be closer to that of acetic acid.

Practical Implications of Bromoacetic Acid's pKa



The relatively low pKa of bromoacetic acid makes it a useful reagent in various chemical reactions. Its ability to readily donate a proton allows it to act as an efficient catalyst or participate in reactions requiring a relatively strong acid.

For example, bromoacetic acid can be used in the synthesis of esters. The acidic proton facilitates the nucleophilic attack of an alcohol on the carbonyl carbon of the bromoacetic acid, leading to ester formation. Its use in such reactions is advantageous because of its relatively high reactivity compared to acetic acid.


Conclusion



The pKa of bromoacetic acid (approximately 2.69) is significantly lower than that of acetic acid, primarily due to the electron-withdrawing inductive effect of the bromine atom. This difference in acidity highlights the profound impact of substituents on molecular properties and has crucial implications in chemical reactivity and applications. Understanding this relationship is fundamental for predicting and manipulating the behavior of organic molecules in various chemical processes.


Frequently Asked Questions (FAQs)



1. What is the exact pKa value of bromoacetic acid? The exact pKa value can vary slightly depending on the solvent and temperature. However, a commonly accepted value is around 2.69 in aqueous solution at room temperature.

2. How does the pKa of bromoacetic acid compare to other halogenated acetic acids? The pKa values decrease as the electronegativity of the halogen increases. Thus, chloroacetic acid has a higher pKa than bromoacetic acid, and iodoacetic acid has an even lower pKa.

3. Can the pKa of bromoacetic acid be experimentally determined? Yes, the pKa can be determined experimentally using various techniques such as potentiometric titration or spectrophotometry.

4. What are some other factors that might influence the pKa of bromoacetic acid? Besides the inductive effect, factors like temperature, solvent polarity, and ionic strength can influence the pKa value.

5. What are the safety precautions when handling bromoacetic acid? Bromoacetic acid is corrosive and toxic. Appropriate safety measures, including the use of gloves, eye protection, and a well-ventilated area, should always be followed during handling and disposal.

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Bromoacetic Acid Pka Bromoacetic acid, a simple halogenated carboxylic acid, serves as a valuable model compound for understanding the influence of substituents on acidity. This article aims to provide a comprehensive understanding of its pKa value, exploring the factors that contribute to its acidity and its implications in various chemical contexts.

pKa Vaules for Organic and Inorganic Bronsted Acids at 25o Ca For strengths of organic acids see E. P. Serjeant and B. Dempsey (eds.), Ionization Constants of Organic Acids in Solution, IUPAC Chemical Data Series No. 23, Pergamon Press, Oxford, UK, 1979. The strength of a base is related to the pK a of its conjugate acid as pK b = 14 - pK a.

Bromoacetic acid | 79-08-3 - ChemicalBook 27 Jan 2025 · Bromoacetic acid (CAS 79-08-3) information, including chemical properties, structure, melting point, boiling point, density, formula, molecular weight, uses, prices, suppliers, SDS and more, available at Chemicalbook.

Acetic acid, bromo- - NIST Chemistry WebBook Use this link for bookmarking this species for future reference. The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected …

Appendix C: Dissociation Constants and pKa Values for Acids at … Bromoacetic acid: CH 2 BrCO 2 H: 1.3 × 10 −3: 2.90: Carbonic acid: H 2 CO 3: 4.5 × 10 −7: 6.35: 4.7 × 10 −11: 10.33: Chloroacetic acid: CH 2 ClCO 2 H: 1.3 × 10 −3: 2.87: Chlorous acid: HClO 2: ... Trichloroacetic acid: CCl 3 CO 2 H: 2.2 × 10 −1: 0.66: Trifluoroacetic acid: CF 3 CO 2 H: 3.0 × 10 −1: 0.52 * Measured at 20°C ...

5.2: Acid Strength and pKa - Chemistry LibreTexts The key idea to remember is this: the stronger the conjugate acid, the weaker the conjugate base. Sulfuric acid is the strongest acid on our list with a pK a value of –10, so HSO 4-is the weakest conjugate base.

E5: Acid Dissociation Constants of Organics - Chemistry LibreTexts 16 Jun 2024 · Successive acid dissociation constants are provided for polyprotic weak acids; where there is ambiguity, the specific acidic proton is identified. To find the K b value for a conjugate weak base, recall that

13.12: Factors affecting Bronsted-Lowry Acidity: Distal Factors Cyclohexanol has a pKa of about 18. It is less acidic than water. It can give up a proton, but the proton is much more likely to be bound to the oxygen than disscociated. Phenol has a pKa of about 9 and is considered mildly acidic.

Appendix C: Dissociation Constants and pKa Values for Acids at … This is “Appendix C: Dissociation Constants and pKa Values for Acids at 25°C”, appendix 3 from the book Principles of General Chemistry (index.html) (v. 1.0M). This book is licensed under a Creative Commons by-nc-sa 3.0 (http://creativecommons.org/licenses/by-nc-sa/

Appendix C: Dissociation Constants and pKa Values for Acids at … This is “Appendix C: Dissociation Constants and pKa Values for Acids at 25°C”, appendix 3 from the book Principles of General Chemistry (v. 1.0). For details on it (including licensing), click here .

What is the pka of bromoacetic acid? - Answers 26 May 2024 · The pKa of an acid is calculated by taking the negative logarithm (base 10) of the acid dissociation constant (Ka). In this case, the pKa would be approximately 5.19. What is the pKa of...

8.3: pKa Values - Chemistry LibreTexts The pKa measures how tightly a proton is held by a Bronsted acid. A pKa may be a small, negative number, such as -3 or -5. It may be a larger, positive number, such as 30 or 50.

Bromoacetic Acid | C2H3BrO2 | CID 6227 - PubChem The pKa of bromoacetic acid is 2.89(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

Bromoacetic acid CAS#: 79-08-3 - ChemicalBook Bromoacetic acid is used in organic synthesis and as an alkylating agent. It is also used as a biochemical for proteomics research. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, dyes and agrochemicals.

The degree of ionization of a 0.1 M bromoacetic acid solution The pH of 0.1M solution of cyanic acid (HCNO) is 2.34. Calculate the ionization constant of the acid and its degree of ionization in the solution.

Bromoacetic Acid Pka Bromoacetic acid, a simple halogenated carboxylic acid, serves as a valuable model compound for understanding the influence of substituents on acidity. This article aims to provide a comprehensive understanding of its pKa value, exploring the factors that contribute to its acidity and its implications in various chemical contexts.

14.12: Factors affecting Bronsted-Lowry Acidity- Distal Factors Consider the pKa of these three, similar, halogenated carboxylic acids: bromoacetic acid, chloroacetic acid and fluoroacetic acid. The pKa of fluoroacetic acid is lower than that of chloroacetic acid, which is lower than that of bromoacetic acid.

Bromoacetic acid | C2H3BrO2 - ChemSpider ChemSpider record containing structure, synonyms, properties, vendors and database links for Bromoacetic acid, 79-08-3, QV1E, KDPAWGWELVVRCH-UHFFFAOYSA-N

Bordwell pKa Table - Organic Chemistry Data 27 Oct 2017 · pKa is an acid dissociation constant used to describe the acidity of a particular molecule. Its value is directly related to the structure of the given compound.

Bromoacetic acid ReagentPlus , = 99.0 79-08-3 - MilliporeSigma Bromoacetic acid is mainly used for the N-terminal bromoacylation of resin bound peptides. It can also be used: To synthesize (Z)-2-(cyclooct-4-en-1-yloxy)acetic acid. To synthesize α-bromo-phenylacetamide. To convert aromatic thiosemicarbazones to thiazolylhydrazones.

Bromoacetic acid - Wikipedia Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Bromoacetic acid is the chemical compound with the formula Br C H 2C O 2H. This colorless solid is a relatively strong alkylating agent.