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    Nitrogen Compounds

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    ahumanbeinginearth
    This document summarizes key concepts about nitrogen compounds for A-level Chemistry. It discusses the formation and structure of primary amines from halogenoalkanes and ammonia. It also describes how nitriles can be formed from halogenoalkanes and cyanide, and how they hydrolyze to form carboxylic acids. Hydroxynitriles form through nucleophilic addition of HCN to carbonyl groups.

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    Nitrogen Compounds

    Uploaded by

    ahumanbeinginearth
    38 views3 pages
    This document summarizes key concepts about nitrogen compounds for A-level Chemistry. It discusses the formation and structure of primary amines from halogenoalkanes and ammonia. It also describes how nitriles can be formed from halogenoalkanes and cyanide, and how they hydrolyze to form carboxylic acids. Hydroxynitriles form through nucleophilic addition of HCN to carbonyl groups.

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    A level chemistry

    Original Title

    19. Nitrogen Compounds

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    This document summarizes key concepts about nitrogen compounds for A-level Chemistry. It discusses the formation and structure of primary amines from halogenoalkanes and ammonia. It also describes how nitriles can be formed from halogenoalkanes and cyanide, and how they hydrolyze to form carboxylic acids. Hydroxynitriles form through nucleophilic addition of HCN to carbonyl groups.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    38 views3 pages

    Nitrogen Compounds

    Uploaded by

    ahumanbeinginearth
    This document summarizes key concepts about nitrogen compounds for A-level Chemistry. It discusses the formation and structure of primary amines from halogenoalkanes and ammonia. It also describes how nitriles can be formed from halogenoalkanes and cyanide, and how they hydrolyze to form carboxylic acids. Hydroxynitriles form through nucleophilic addition of HCN to carbonyl groups.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
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    CAIE Chemistry A-level

    19: Nitrogen Compounds


    Notes

    This work by PMT Education is licensed under https://bit.ly/pmt-cc


    https://bit.ly/pmt-edu-cc CC BY-NC-ND 4.0

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    Primary Amines
    ​
    Primary amines have the formula ​RNH​2​ where R is an alkyl group. The structure of
    ethylamine​ is shown below:

    Formation of Alkyl Amines


    Alkyl amines​ can be made from ​halogenoalkanes​:
    ○ Heat the halogenoalkane in a sealed tube with ​concentrated ammonia​ in an
    ethanol solvent (reflux cannot be used as ammonia is too volatile). To ensure
    that a ​primary amine​ is formed, rather than an ammonium salt, an ​excess of
    ammonia​ must be used.
    ○ E.g. Using 1-chloroethane:
    CH​3​CH​2​Cl + NH​3​ → CH​3​CH​2​NH​3​+​Cl​-
    CH​3​CH​2​NH​3​+​Cl​-​ + NH​3​ → CH​3​CH​2​NH​2​ + NH​4​+​Cl​-

    Nitriles and Hydroxynitriles

    Formation of Nitriles
    Nitriles are formed when a halogenoalkane reacts with ​cyanide​. The reaction requires
    warm, ethanolic​ ​potassium cyanide​ (ethanolic means dissolved in ethanol).

    Nucleophilic Addition
    When aldehydes and ketones react with HCN to form ​hydroxynitriles​, a​ nucleophilic
    addition​ reaction occurs.

    The ​carbonyl bond​ (C=O) is ​highly polar​. The negative​ cyanide ion​ acts as a
    nucleophile​ and attacks the slightly positive carbon atom. The C=O bond breaks, leaving
    only a ​single bond ​between the ​carbon and oxygen ​atoms. The negatively charged
    oxygen then bonds to a ​hydrogen ion​ (from HCN or any added acid).

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    Hydrolysis
    Nitriles​ can undergo ​hydrolysis​ to form ​carboxylic acids​. The C≡N nitrile bond reacts with
    water to produce the carboxylic acid.

    ● Acid hydrolysis
    The nitrile is heated under ​reflux​ with a dilute acid (such as ​hydrochloric acid​). A
    carboxylic acid​ and a ​salt​ are produced.
    The reaction of propanenitrile with a dilute acid:

    CH​3​CH​2​CN + 2H​2​O + HCl → CH​3​CH​2​COOH + NH​4​Cl

    ● Alkaline hydrolysis
    The nitrile is heated under​ reflux​ with an alkali (such as ​sodium hydroxide​). This
    produces a ​carboxylic acid​ and ​ammonia​. The reaction takes place in two stages.
    First, carboxylate ions are produced (e.g.​ sodium carboxylate​ forms if sodium
    hydroxide is used). A ​strong acid​ must then be added to provide hydrogen ions to
    liberate the carboxylic acid. Hydrochloric acid is commonly used.

    The formation of propanoic acid from propanenitrile:

    Stage 1: CH​3​CH​2​CN + NaOH + H​2​O → CH​3​CH​2​COONa + NH​3

    Stage 2: CH​3​CH​2​COONa + HCl → CH​3​CH​2​COOH + NaCl

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