Nitrogen compounds Flashcards

1
Q

Synthesis of amines/phenylamines

A
  1. Nucleo sub of RX
  2. Reduction of amides
  3. Reduction of nitriles
    $. Reduction of nitrobenzene to phenylamine (ONLY WAY!)
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2
Q

R&C for nucleo sub of RX

A

Mono-sub: Excess NH3 in ethanol, heat in sealed tube

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3
Q

R&C for reduction of amides to amines

A

LiAlH4 in dry ether

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4
Q

R&C for reduction of nitriles to amines

A

LiAlH4 in dry ether OR H2, Ni, heat

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5
Q

Reactions of amines/ phenylamines

A
  1. Condensation of amines to amides
  2. Acid-base reaction
  3. Phenylamines: Electo-sub
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5
Q

Distinguishing test for phenylamines

A

Electro-sub
Observations:
1. Orange Br2 decolourises
2. White ppt of 2.4.6-tribromophenylamine formed
3. White fumes of HBr

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5
Q

R&C for nitrobenzene to phenylamine

A
  1. Sn, conc HCl. heat under reflux
  2. NaOH (aq)
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6
Q

R&C for acid-base rxn for amines

A

HCl(aq)
* All amines are lewis bases

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7
Q

R&C for condensation of amines to amides

A

anhydrous acyl chloride, rtp

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8
Q

Why are phenylamines more reactive towards electrosub than phenols?

A
  1. N is less EN than O
  2. LP of electrons on N delocalises into benzene ring to a larger extent than LP of electrons on O
  3. Benzene in phenylamine more electron rich than in phenol
  4. Phenylamines more reactive
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9
Q

Synthesis of amides

A
  1. Condensation of amines to amides (ONLY ONE WAY)
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10
Q

Reactions of amides

A
  1. Hydrolysis
  2. Reduction
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11
Q

Explain the basicity of nitrogen compounds

A
  • electron-donating –> electron density on N increases –> LP of electrons more available for donation –> Strong base
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12
Q

R&C for hydrolysis of amides and products

A

Acidic Hydrolysis:
R&C: H2SO4, heat
Basic Hydrolysis:
R&C: NaOH, heat

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