Synthetic Routes Flashcards

1
Q

Alkane to haloalkane

A
  • radical substitution
  • homolytic fission
  • Cl2, UV light
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2
Q

Alkene to dihaloalkane

A
  • electrophilic addition
  • heterolytic fission
  • halogenation
  • Br2
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3
Q

Alkene to alcohol

A
  • electrophilic addition
  • heterolytic fission
  • hydration
  • steam >100’C, H3PO4 catalyst
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4
Q

Alkene to haloalkane

A
  • electrophilic addition
  • heterolytic fission
  • halogenation
  • HBr
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5
Q

Alkene to alkane

A
  • electrophilic addition
  • heterolytic fission
  • hydration
  • H2, Ni catalyst
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6
Q

Haloalkane to alcohol

A
  • nucleophilic substitution
  • heterolytic fission
  • hydrolysis
  • NaOH(aq), reflux
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7
Q

Alcohol to alkene

A
  • heterolytic fission
  • dehydration
  • conc. H2SO4 or conc. H3PO4
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8
Q

Alcohol to haloalkane

A
  • heterolytic fission
  • halogenation
  • HBr from NaBr/H2SO4
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9
Q

Alcohol to ester **

A
  • heterolytic fission
  • esterification
  • carboxylic acid, conc. H2SO4
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10
Q

Primary alcohol to aldehyde

A
  • heterolytic fission
  • oxidation
  • H2SO4/K2Cr2O7
  • distillation (heat)
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11
Q

Primary alcohol to carboxylic acid

A
  • heterolytic fission
  • oxidation
  • H2SO4/K2Cr2O7
  • reflux (heat)
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12
Q

Aldehyde to carboxylic acid

A
  • heterolytic fission
  • oxidation
  • H2SO4/K2Cr2O7
  • reflux (heat)
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13
Q

Secondary alcohol to ketone

A
  • heterolytic fission
  • oxidation
  • H2SO4/K2Cr2O7
  • reflux (heat)
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14
Q

Tertiary alcohol…

A

… resistant to oxidation

no reaction

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15
Q

List all the possible mechanisms

A
  • radical substitution (alkanes)
  • electrophilic addition (alkenes)
  • nucleophilic substitution (haloalkanes)
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16
Q

List all the types of bond breaking

A
  • homolytic fission (forms radicals)

- heterolytic fission (forms ions)

17
Q

List all the types of reactions (synthetic routes)

A
  • hydration (alkene to alkane/alcohol)
  • halogenation (alkene/alcohol to di/haloalkane)
  • hydrolysis (haloalkane to alcohol)
  • dehydration (alcohol to alkene)
  • esterification (alcohol to ester)
  • oxidation (alcohol to aldehyde/ carboxylic acid/ketone)
18
Q

Radical

A

an unpaired electron

19
Q

Nucleophile

A

donates a lone pair of electrons

20
Q

Electrophile

A

accepts a pair of electrons