Organic Chemistry pKa Values

Vocabulary flashcards covering common organic and inorganic functional groups and compounds along with their corresponding pKa values.

Protonated Carbonyl

A carbonyl compound that has been protonated, having an approximate $\text{p}K_a$ value of $-7$.

Hydronium Ion / Protonated Alcohol or Ether

A protonated water molecule ($\text{H}_3\text{O}^+$) or protonated alcohol/ether ($\text{ROH}_2^+$), having an approximate $\text{p}K_a$ value of $\sim 0$.

Carboxylic Acid

An organic compound containing a carboxyl group ($\text{RCOOH}$), having an approximate $\text{p}K_a$ value of $5$.

Phenol

An aromatic compound with a hydroxyl group directly bonded to a benzene ring, having an approximate $\text{p}K_a$ value of $10$.

Alcohol

An organic compound containing a hydroxyl group ($\text{ROH}$), having an approximate $\text{p}K_a$ value of $16$.

Water

An inorganic chemical compound ($\text{H}_2\text{O}$), having an approximate $\text{p}K_a$ value of $16$.

Alpha Proton (Adjacent to Carbonyl)

A proton attached to a carbon atom directly adjacent to a carbonyl group, having an approximate $\text{p}K_a$ value of $20$.

Proton Between Two Carbonyls

An acidic proton situated on a carbon bonded between two carbonyl groups, having an approximate $\text{p}K_a$ value of $10$.

Terminal Alkyne

A hydrocarbon containing a carbon-carbon triple bond at the end of the carbon chain, having an approximate $\text{p}K_a$ value of $25$.

Amine

A neutral organic nitrogen compound, having an approximate $\text{p}K_a$ value of $35$.

Protonated Amine

An ammonium species formed by protonating an amine ($\text{RNH}_3^+$), having an approximate $\text{p}K_a$ value of $10$.

Aryl Proton / Vinyl Proton

A proton directly attached to an aromatic ring carbon or an $sp^2$ alkenic carbon, having an approximate $\text{p}K_a$ value of $40$.

Alkane

A saturated hydrocarbon containing only single bonds, having an approximate $\text{p}K_a$ value of $50$.

Hydroiodic Acid (HI)

A strong inorganic acid ($\text{HI}$) with a $\text{p}K_a$ value of $-10$.

Hydrobromic Acid (HBr)

A strong inorganic acid ($\text{HBr}$) with a $\text{p}K_a$ value of $-8$.

Hydrochloric Acid (HCl)

A strong inorganic acid ($\text{HCl}$) with a $\text{p}K_a$ value of $-7$.

Sulfuric Acid (H2SO4)

A strong inorganic acid ($\text{H}_2\text{SO}_4$) with a $\text{p}K_a$ value of $-3$.

Carbocations

Positively charged carbon intermediates whose adjacent protons have an approximate $\text{p}K_a$ value of $-3$.

Nitric Acid (HNO3)

An inorganic acid ($\text{HNO}_3$) with an approximate $\text{p}K_a$ value of $\sim 0$.

Hydrofluoric Acid (HF)

An inorganic acid ($\text{HF}$) with a $\text{p}K_a$ value of $3$.

Hydrogen Nitride (HN3)

Hydrazoic acid ($\text{HN}_3$) with a $\text{p}K_a$ value of $5$.

Hydrogen Cyanide (HCN)

An inorganic acid ($\text{HCN}$) with a $\text{p}K_a$ value of $9$.