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    L1Org Lec1B Amines Annotated

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    Amines have basic and nucleophilic properties. They have higher boiling points than alcohols due to hydrogen bonding. Amines are commonly found in biological systems and pharmaceutical drugs. They can be synthesized through alkylation of ammonium salts or reduction of nitrogen-containing compounds to form primary, secondary, or tertiary amines.

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    L1Org Lec1B Amines Annotated

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    maddie.jng
    3 views18 pages
    Amines have basic and nucleophilic properties. They have higher boiling points than alcohols due to hydrogen bonding. Amines are commonly found in biological systems and pharmaceutical drugs. They can be synthesized through alkylation of ammonium salts or reduction of nitrogen-containing compounds to form primary, secondary, or tertiary amines.

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    annotated lecture notes

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    L1Org_Lec1B_amines_annotated (3)

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    Amines have basic and nucleophilic properties. They have higher boiling points than alcohols due to hydrogen bonding. Amines are commonly found in biological systems and pharmaceutical drugs. They can be synthesized through alkylation of ammonium salts or reduction of nitrogen-containing compounds to form primary, secondary, or tertiary amines.

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    3 views18 pages

    L1Org Lec1B Amines Annotated

    Uploaded by

    maddie.jng
    Amines have basic and nucleophilic properties. They have higher boiling points than alcohols due to hydrogen bonding. Amines are commonly found in biological systems and pharmaceutical drugs. They can be synthesized through alkylation of ammonium salts or reduction of nitrogen-containing compounds to form primary, secondary, or tertiary amines.

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    of 18

    Amines

    Properties

    Basicity and nucleophilicity

    Examples

    Synthesis
    A Note on Arrows

    ‘Arrow pushing’ shows the movement of electrons

    Arrows must start where there are electrons!

    Arrows end where a bond or charge is formed!


    Amines

    primary secondary tertiary quaternary


    amine amine amine ammonium
    salt
    Amines

    Amines are basic:

    pKa 10.5

    Good water solubility


    Amines

    Amines are nucleophilic:


    Amines

    Non-nucleophilic bases: hindered lone pair


    Amines

    Weak hydrogen bond donors and acceptors

    Lower boiling points than alcohols


    Amines

    Coordination of transition metals


    Amines

    Generally smell bad…

    cadaverine putrescine

    …or really bad


    Amines

    A common group in ‘energetic materials’

    Stability of N2
    Amines

    Ubiquitous in biology

    adrenaline serotonin
    Amines

    Common in pharmaceuticals: ‘alkaloid’ drugs

    morphine
    Amines
    Common in pharmaceuticals: ‘alkaloid’ drugs

    serotonin

    bufotenin
    Amines

    Preparation by alkylation of ammonium:

    Over-alkylation is a problem:
    Amines

    Preparation by reduction of nitrogen compounds:

    Primary amines
    Amines

    Preparation by reduction of nitrogen compounds:

    Primary amines
    Amines

    Preparation by reduction of nitrogen compounds:

    Primary, secondary and tertiary amines


    Amines

    Reductive amination: reduction of an imine to an amine

    Secondary amines

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