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Organic Chemistry: Functional Groups and Acidity

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  • What is the approximate pKa of hydrochloric acid (HCl)?

    The pKa of HCl is approximately \(-7\), indicating it is a very strong acid.

  • Order of acidity for α-protons in carbonyl compounds

    α-protons acidity order: aldehydes > ketones > esters > amides.

  • What is the pKa range for water (H2O)?

    The pKa of water is approximately \(0\).

  • Define a primary alcohol functional group

    A primary alcohol has the structure OH attached to a carbon bonded to one other carbon (R-CH2-OH).

  • What is the pKa range for phenol (Ar-OH)?

    Phenol has a pKa around \(9-11\), making it more acidic than typical alcohols.

  • Identify the functional group: R-CO-R'

    This is a ketone, characterized by a carbonyl group bonded to two carbon atoms.

  • What is the pKa range for carboxylic acids?

    Carboxylic acids have a pKa around \(4-5\), indicating moderate acidity.

  • Describe a tertiary amine

    A tertiary amine has a nitrogen atom bonded to three carbon groups and no hydrogen atoms (R3N).

  • What is the pKa range for alkynes (terminal)?

    Terminal alkynes have a pKa around \(25\), showing relatively acidic C-H bonds.

  • Name the functional group: R-COOH

    This is a carboxylic acid, containing a carbonyl and hydroxyl group on the same carbon.

  • What is the pKa range for amides?

    Amides have a pKa approximately \(15-16\), less acidic than carboxylic acids.

  • Define an ether functional group

    An ether has an oxygen atom bonded to two alkyl or aryl groups (R-O-R').

  • What is the pKa range for thiols (R-SH)?

    Thiols typically have pKa values around \(10-12\), similar to phenols.

  • Identify the functional group: R-C≡N

    This is a nitrile, characterized by a carbon triple-bonded to nitrogen.

  • What is the pKa range for aldehydes α-protons?

    α-protons of aldehydes have pKa values around \(17-20\), more acidic than ketones.

  • Describe a quaternary ammonium ion

    A nitrogen atom bonded to four alkyl groups carrying a positive charge (R4N+).

  • What is the pKa range for alkanes (sp3 C-H bonds)?

    Alkanes have very high pKa values, typically > \(60\), indicating very weak acidity.

  • Name the functional group: R-COOR'

    This is an ester, with a carbonyl adjacent to an ether oxygen.

  • What is the pKa range for secondary amines?

    Secondary amines have pKa values around \(33-40\), indicating weak acidity.

  • Define an anhydride functional group

    An anhydride consists of two acyl groups bonded to the same oxygen atom (R-CO-O-CO-R').

  • What is the pKa range for ketones α-protons?

    Ketones have α-proton pKa values around \(20-25\), less acidic than aldehydes.

  • Describe a primary halide

    A primary halide has a halogen atom bonded to a carbon attached to only one other carbon (R-CH2-X).

  • What is the pKa range for secondary thiols?

    Secondary thiols have pKa values similar to primary thiols, generally around \(10-12\).

  • Identify the functional group: R-NO2

    This is a nitro group, with nitrogen bonded to two oxygens and one carbon.

  • What is the pKa range for primary amines?

    Primary amines have pKa values around \(33-40\), indicating weak acidity.

  • Define a thioether (sulfide)

    A sulfur atom bonded to two alkyl or aryl groups (R-S-R').

  • What is the pKa range for esters α-protons?

    Esters have α-proton pKa values around \(25-30\), less acidic than ketones.

  • Describe a tertiary alcohol

    A tertiary alcohol has the hydroxyl group attached to a carbon bonded to three other carbons (R3C-OH).