ORGANIC REAGENTS Flashcards by Sagana Baskar

Alkane to Haloalkane

UV light or heat
gaseous halogen (Cl2)

free radical substitution
homolytic fission

Cl₂ ➜ 2Cl

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Alkane to Combustion Products

Oxygen 2 Heat

Combustion/incomplete

CₓH₂ₓ₊₂ + O₂ ➜ CO₂ + H₂O

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Alkene to Alkane

Nickel catalyst, H₂ gas

Hydrogenation

C=C + H₂ ➜ C-C

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Alkene to Haloalkane (one halogen)

Hydrogen halides, room temp

electrophilic addition
heterolytic fission
carbocation

CH₂=CH₂ + HCL ➜ CH₃CH₂Cl

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Alkene to Haloalkane (dihalo-)

aqueous halogen, room temp

Electrophilic addition
Heterolytic fission
Carbocation

CH₂=CH₂ + Cl₂ ➜ CH₃CHCl₂

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Alkene to Alcohol

phosphoric acid catalyst, steam

Hydration

CH₂ = CH₂ + H₂O ⇌ CH₃CH₂OH

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Alkene to Polymer

H2 gas and Ni catalyst

Free radical addition

nCH₂ = CH₂ ➜ [CH₂-CH₂]ₙ & Ra* + CH₂ = CH₂ ➜ RaCH₂CH₂ *

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Haloalkane

Haloalkane to Alcohol (alkali)

dilute NaOH or KOH

Nucleophilic sub
hydrolysis

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Haloalkane

Haloalkane to Alcohol (water)

heat warmly, use H₂O

nucleophilic sub
hydrolysis

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Haloalkane

Haloalkane to Amine

heat with NH3 in ethanol

nucleophilic sub

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Haloalkane

Haloalkane to Nitrile

warm NaCN/KCN, dilute ethanol (CN- + HCl)

Nucleophilic sub

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Alcohols

Alcohol to Combustion Products

oxygen 2 heat

combustion/incomplete

CH₃OH + 3/2O₂ ➜ CO₂ + 2H₂O

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Alcohols

Alcohol to Aldehyde

Acidified (H₂SO₄) Potassium Dichromate (K₂Cr₂O₇) to be used to distill at temp to collect aldehyde

primary alcohol

CH₃CH₂OH + [O] ➜ CH₃CHO + H₂O

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Alcohols

Alcohol to Ketone

Heat under reflux + H2SO4 and potassium dichromate

secondary alcohol

CH₃CH(OH)CH₃ + [O] ➜ CH₃COCH₃ + H₂O

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Alcohols

Alcohol to Carboxylic Acid

heat under reflux + acidified potassium dichromate

Primary alcohol

CH₃CH₂OH + 2[O] ➜ CH₃COOH + H₂O

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Alcohols

Alcohol to Alkene

Heat + conc H2SO4

Any alcohol
Dehydration

CH₃CH₂OH –(H₂SO₄)–> C=C

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Alcohols

Alcohol to Haloalkane

sodium halide + H₂SO₄

Any alcohol
halide substitution

CH₃CH₂OH + NaBr ➜ CH₃CH₂Br + Na⁺

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Alcohols

Alcohol to ester

heat with conc H₂SO₄ and carboxylic acid OR ACID ANYHYDRIDE

condensation - esterfication

R - OH + H-O - C = O - R
reflux

OH from carboxylic acid and H from alcohol make H₂O

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Carbonyls

Aldehyde to carboxylic acid

H₂SO₄ + potassium dichromate and heat under reflux

Oxidation

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Carbonyls

Aldehyde or ketone to alcohol

NaBh₄ (H- attacks C), aq or alcoholic solution

Nucleophilic addition - reduction
1°or 2° alcohol

Carbonyls

Aldehyde or ketone to hydroxynitrile

HCN [i.e. NaCN(aq)/H+(aq)]

nucleophilic addition HCN

Carboxylic acids and derivatives

Carboxylic to ester

Alcohol + carboxylic acid + conc H₂SO₄
condensation

Carboxylic acids and derivatives

Carboxylic to salts

Any metal in solution

neutralisation

Carboxylic acids and derivatives

Carboxylic to Acyl chloride

thionyl chloride SOCL2
acylation

# Carboxylic acids and derivatives Acid Anhydride to ester

`alcohol + acid an = ester` condensation

# Carboxylic acids and derivatives Acyl chloride to Ester

`alcohol at room temp` condensation

# Carboxylic acids and derivatives Acyl chloride to Amide

`conc ammonia (prim) or primary amine(sec)` condensation

# Carboxylic acids and derivatives Ester to carboxylic acid and Alcohol

`dilute HCL or H2SO4 and heat` acid hydrolysis

# Carboxylic acids and derivatives Ester to carboxylate and Alcohol

`NaOH and heat` alkaline hydrolysis

# Amines, Amino acids and Amides Amine to salt

`HCl at rtp` neutralisation

# Amines, Amino acids and Amides Amino acid to Ester

`Alcohol with conc H₂SO₄ under reflux or acyl chloride at rtp` condensation

# Amines, Amino acids and Amides Amino acid to salt

`HCl at rtp` neutralisation

# Amines, Amino acids and Amides Amino acid to salt

`NaOH at rtp` neutralisation

# Nitriles Hydroxynitrile to Amine

`(H2 gas and Ni catalyst)` Reduction

# Nitriles Nitrile to Amine

`LiAlH₄, H2 gas and Ni catalyst` Reduction

# Nitriles Hydroxynitrile to Carboxylic acid

`dilute HCl and H2SO4 and heat` Oxidation, acid hydrolysis

# Condensation Polymers Polyester to Carboxylic acid & Alcohol

`dilute HCl under reflux` acid hydrolysis

# Condensation Polymers Polyester to Carboxylate & Alcohol

`dilute NaOH under reflux` alkaline hydrolysis

# Condensation Polymers Polyamide to Carboxylic acid & Alcohol

`dilute HCl + reflux` acid hydrolysis

# Condensation Polymers Polyamide to Carboxylate & Alcohol

`dilute NaOH with heat` alkaline hydrolysis

# Aromatic Benzene to Nitrobenezene

`conc H₂SO₄ & conc HNO₃ at reflux` Electrophilic substitution | HNO3 + H2SO4 ➜ NO2⁺ + HSO4⁻ + H2O

# Aromatic Benzene to Halobenzene

`Bromobenzene = Br2 & FeBr3 and Chlorobenzene = Cl2 and AlCl3` Electrophilic substitution | Br2 + FeBr3 ➜ Br⁺ + Febr4⁻

# Aromatic Benzene to Alkylbenzene

`AlCl₃ & under reflux` Electrophilic substitution - alkylation | AlCl3 + CH3Cl ➜ AlCl4⁻ + CH3⁺

# Aromatic Benzene to Acylbenzene

`AlCl₃ and CH3COCl` Electrophilic substitution - acylation - carbo acid ion attached to benzene and then becomes ketone | AlCl3 + CH3COCl ➜ AlCl4⁻ + CH3CO⁺

# Aromatic Benzene to Cyclohexane

`Nickel catalyst, H₂ gas` Hydrogenation

# Aromatic Nitrobenzene to Phenylamine

`Sn and conc HCl and heated under reflux, then NaOH is used to neutralise` Reduction then Neutralisation

# Aromatic Phenol to Bromophenol

`2,4 directing!` Electrophilic substitution bromine water - Br2

# Aromatic Phenol to Nitrophenol

`2,4 directing` Electrophilic substitution Dilute HNO3

# Aromatic Phenol to Phenoxide

`Acid & Base = add water or Neutralisation = add metal`