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Amines are derivatives of

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Ammonia

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Ammonia (symbol)

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NH3

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IUPAC names for amines

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-e in corresponding alkane name is replaced with -amine number chain to show position of amine groups and substituents alkyl groups attached to N is indicated with the prefix N- and the alkyl name (put in front of amine name)

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IUPAC Name: CH3-CH3

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Ethane

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IUPAC Name: CH3-CH2-NH2

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Ethanamine

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IUPAC Name: CH4

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Methane

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IUPAC Name: CH3-NH2

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Methanamine

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IUPAC Name: CH3-CH2-CH2-NH2

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1-Propanamine

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IUPAC Name: CH3 -- CH -- CH3 | NH2

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2-Propanamine

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IUPAC Name: CH3 -- CH -- CH2 -- CH3 | NH2

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2-Butanamine

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IUPAC Name: CH3 | CH3 -- CH -- CH2 -- CH2 -- NH

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3-Methyl-1-butanamine

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IUPAC Name: H | CH3 -- N -- CH2 -- CH2 -- CH2 -- CH3

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N-methyl-1-butanamine

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Common Name of amines

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List names of alkyl groups in ABC order in front of "amine"

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CN: CH3-CH2-NH2

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Ethylamine

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CN: CH3-NH-CH3

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Dimethylamine

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CN: CH3 -- N -- CH2 -- CH3 | CH3

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Ethyldimethylamine

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CN: CH3-CH2-CH2-NH2

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Propylamine

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IUPAC Name: CH3 -- CH2 -- N -- CH2 | CH3

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N,N-Dimethylethanamine

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CN: CH3 -- CH2 -- N -- CH2 | CH3

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Ethyldimethylamine

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Primary, secondary, or tertiary: CH3-CH2-CH2-NH2

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Primary

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Primary, secondary, or tertiary: CH3 -- CH2 -- N -- CH2 | CH3

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Tertiary

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Draw the condensed structural formula: 2-pentanamine

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NH2 | CH3--CH--CH2--CH2--CH3

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Draw the condensed structural formula: N-methlyl-1-butanamine

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CH3--CH2--CH2--CH2--NH--CH3

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IUPAC names with 2 functional groups

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Oxygen-containing group has priority over an NH group NH group is named as "amino"

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IUPAC name: NH2 | CH3 -- CH -- CH2 -- OH

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2-Amino-1-propanol

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IUPAC name: NH2 O | || CH3--CH--CH2--C--CH3

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4-Amino-2-pentanone

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IUPAC name: NH2 O | || CH3--CH--CH2--C--OH

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3-Aminobutanoic acid

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Name as a substituent: Amide

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Amino

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Name as a substituent: Aldehyde

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Formyl

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Name as a substituent: Ketone

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Oxo

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Name as a substituent: Alcohol

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Hydroxy

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Name as a substituent: Amine

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Amino

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Name as a substituent: Alkane

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Alkyl

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Name as a substituent: Halide

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Halo

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Amine of benzene

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Aniline

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Common name: CH3-N-CH2-CH3 | H

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Ethylmethylamine

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IUPAC name: CH3-N-CH2-CH3 | H

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N-methylethanamine

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Common name: CH3 | CH3-CH2-N-CH2-CH2-CH3

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Butylethylmethylamine

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IUPAC name: CH3 | CH3-CH2-N-CH2-CH2-CH3

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N-ethyl-N-methyl-1-butanamine

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What bonds do amine contain? What does this allow?

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N-H bonds Primary and secondary amines form hydrogen bonds with water

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What forms hydrogen bonds with water?

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Primary and secondary amines

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What bonds do primary and secondary amines form?

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Hydrogen bonds with water

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What is more electronegative? Oxygen or Nitrogen?

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Oxygen

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What amines are soluble?

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Soluble in water if they have 1 to 6 carbon atoms

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What is more soluble? Primary or tertiary amines?

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Primary amines are more soluble tertiary amines are least soluble

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Which has the highest boiling point? Which are soluble in water? A. CH3-CH2-CH2-NH2 B. CH3-CH2-NH-CH3 C. CH3-CH2-CH2-CH3

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Highest boiling point: A. CH3-CH2-CH2-NH2 Soluble in water: B. CH3-CH2-NH-CH3 A. CH3-CH2-CH2-NH2

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Amines react as _______ in water

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Bases

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H atom from H2O is attracted to what atom?

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The N atom

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H-N-H + HOH | H

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H | H - N+ - H + OH- | H

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When are amine salts formed?

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When an amine is neutralized by an acid

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How are amine salts named?

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Replace the -amine with -ammonium, followed by the name of the negative ion

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Methylamine + H-Cl ---> (neutralization)

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Methylammonium chloride

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Dimethylamine + H-Cl ---> (neutralization)

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Dimethylammonium chloride

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Amine salts: Liquid/Solid at room temp

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Solids

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Amine salts: Soluble or insoluble

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Soluble

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What are amine salts used for ?

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Drugs (Sudafed, Benadryl)

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Amine salts are ________ ___________.

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Ionic compounds

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Cocaine is a

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Amine salt

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Cocaine reacted with NaOH produces

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Crack

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CH3-CH2-NH2 + H2O

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CH3-CH2-NH3+OH-

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CH3-CH2-NH2 + HCl

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CH3-CH2-NH3+Cl-

CH18 – Chemistry – Flashcards

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