Amines & Amides: Reactions

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Last updated 8:36 AM on 4/25/26
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9 Terms

1
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Reduction of nitrobenzene to produce amine

RnCs:

  1. Sn, concnetrated HCl, heat

  2. (after salt is formed) NaOH(aq)

Note:

  • product first forms the salt C6H5NH3+Cl-, then excess NaOH is added to liberate phenylamine

<p>RnCs: </p><ol><li><p>Sn, concnetrated HCl, heat</p></li><li><p>(after salt is formed) NaOH(aq)</p></li></ol><p></p><p>Note: </p><ul><li><p>product first forms the salt C<sub>6</sub>H<sub>5</sub>NH<sub>3</sub><sup>+</sup>Cl<sup>-</sup>, then excess NaOH is added to liberate phenylamine</p></li></ul><p></p>
2
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Reaction of amines with acids

RnCs: mineral acids or carboxylic acids, room temperature

Note:

  • soluble ionic salts are formed through acid-base reactions involving the insoluble amines

<p>RnCs: mineral acids or carboxylic acids, room temperature</p><p>Note:</p><ul><li><p>soluble ionic salts are formed through acid-base reactions involving the insoluble amines</p></li></ul><p></p>
3
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Regenerating amine through acid-base reactions

  • in an organic solvent in a separating funnel, first react with mineral acid/carboxylic acid

  • and obtain soluble ionic salt as it is insoluble in the solvent

  • react salt with strong base eg NaOH

<ul><li><p>in an organic solvent in a separating funnel, first react with mineral acid/carboxylic acid</p></li><li><p>and obtain soluble ionic salt as it is insoluble in the solvent </p></li><li><p>react salt with strong base eg NaOH</p></li></ul><p></p>
4
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Nucleophilic substitution to form primary, secondary and tertiary amines

RnCs: NH3 OR amine in ethanol, halogenoalkane heated under high pressure

Note:

  • lone pair on nitrogen(amine acts as a nucleophile) causes further reactions ot occur to form more substituted amines

<p>RnCs: <u>NH<sub>3</sub> OR amine</u> in ethanol, halogenoalkane heated under high pressure</p><p>Note: </p><ul><li><p>lone pair on nitrogen(amine acts as a nucleophile) causes further reactions ot occur to form more substituted amines </p></li></ul><p></p>
5
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Condensation to form amides

RnCs: acyl chlorides, primary/secondary amines in excess

Note:

  • in excess to ensure complete reaction as amines can react with HCl in acid-base reaction

<p>RnCs: acyl chlorides, primary/secondary amines in excess</p><p>Note:</p><ul><li><p>in excess to ensure complete reaction as amines can react with HCl in acid-base reaction</p></li></ul><p></p>
6
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Electrophilic substitution of phenylamine to form 2,4,6-tribromophenylamine

RnCs: aqueous bromine, room temperature

Observation: yellow-orange solution declourise, white ppt formed (white fumes of HBr may nto be observed as HBr aqueous solution)

Notes:

  • -NH2 group is 2,4-directing

<p>RnCs: aqueous bromine, room temperature</p><p>Observation: yellow-orange solution declourise, white ppt formed (white fumes of HBr may nto be observed as HBr aqueous solution)</p><p></p><p>Notes:</p><ul><li><p>-NH<sub>2</sub> group is 2,4-directing </p></li></ul><p></p>
7
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Reduction of amides

RnCs: LiAlH4 in dry ether

<p>RnCs: LiAlH<sub>4</sub> in dry ether</p>
8
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acidic hydrolysis of amides

RnCs: dilute H2SO4, heat under reflux

<p>RnCs: dilute H<sub>2</sub>SO<sub>4</sub>, heat under reflux </p>
9
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alkaline hydrolysis (followed by acidification)

RnCs: dilute NaOH, heat under reflux, followed by acidification with dilute H2SO4 (to yield caroxylic acid)

Note:

  • distinguishing test for amines as ammonia will be produced upom undergoing alkalin hydrolysis