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Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
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The titration of a polyprotic base such as sodium carbonate with a strong acid such as hydrochloric acid results in two equivalence points on the titration curve. At the first equivalence point, the carbonate ions in the base are completely converted to bicarbonate ions. The second equivalence point corresponds to the complete conversion of bicarbonate ions to carbonic acid, which dissociates into carbon dioxide and water. The region before the first equivalence point corresponds to the...
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Sodium Hydroxide versus Phenol Chemical Matrixectomy.

Clark K Brackney1, Jennifer A Kipp1, Gregory Russell2

  • 1*Department of Orthopaedic Surgery and Rehabilitation, Wake Forest University School of Medicine, Atrium Wake Forest Baptist Medical Center, Winston-Salem, NC.

Journal of the American Podiatric Medical Association
|August 27, 2025
PubMed
Summary
This summary is machine-generated.

Chemical matrixectomy for ingrown toenails using sodium hydroxide (NaOH) or phenol shows similar recurrence and reoperation rates. This study found no significant difference between the two chemical agents in treating painful nail edges.

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Area of Science:

  • Podiatry
  • Dermatology
  • Surgical Procedures

Background:

  • Chemical matrixectomy (CM) is a standard procedure for painful ingrown toenails.
  • Sodium hydroxide (NaOH) and phenol are commonly used chemical agents for germinal nail matrix destruction.
  • Evaluating the efficacy of different chemical agents in CM is crucial for optimal patient outcomes.

Purpose of the Study:

  • To compare the recurrence and reoperation rates of chemical matrixectomy using sodium hydroxide (NaOH) versus phenol.
  • To determine if there is a statistically significant difference in outcomes between NaOH and phenol CM.
  • To provide evidence-based insights for selecting chemical agents in CM procedures.

Main Methods:

  • Retrospective review of 192 patient medical records over a 2-year period.
  • Analysis of partial nail avulsions performed using either phenol or NaOH.
  • Standardized CM procedure performed by three podiatric physicians.

Main Results:

  • A total of 46 nail borders were treated with phenol and 258 with NaOH.
  • The reoperation rate per border for phenol CM was 6.5%, compared to 7.8% for NaOH (P = .89).
  • The recurrence rate per border for phenol CM was 10.9%, compared to 8.1% for NaOH (P = .58).

Conclusions:

  • This study found no statistically significant difference in reoperation or recurrence rates between sodium hydroxide and phenol for chemical matrixectomy.
  • Both chemical agents appear to be equally effective in the long-term management of ingrown toenails.
  • The choice between NaOH and phenol may not significantly impact patient outcomes regarding recurrence and reoperation.