Functional Groups Transformations Flashcards
Alkane -> Halogenoalkane
X2 + UV light
X2 = for example Cl2 or Br2
Alkene -> Alkane
H2 + Nickel catalyst
Alkene -> Halogenoalkane
HX
HX = for example HCl or HBr
Halogenoalkane -> Alkene
KOH + Ethanol + Reflux
Halogenoalkane -> Alcohol
Aqueous KOH + Reflux
Alcohol -> Chloroalkane
PCl5 or HCl
Alcohol -> Bromoalkane
KBr + H2SO4
Alcohol -> Alkene
Conc H3PO4
Alkene -> Alcohol
Steam + H3PO4
Alkene -> Dihalogenoalkane
X2
X2 = for example Cl2 or Br2
Alcohol -> Iodoalkane
I2 + Red phosphorus + Reflux
Alkene -> Diol
Acidified KMnO4
Alcohol -> Aldehyde
Potassium Dichromate + H2SO4 + Distillation
Alcohol -> Ketone
Potassium Dichromate + H2SO4 + Reflux
Aldehyde/Ketone -> Hydroxynitrile
HCN + Ethanol + Reflux
Aldehyde -> Carboxylic acid
Potassium Dichromate + H2SO4 + Reflux
Alcohol -> Ester
Carboxylic acid + acid catalyst
OR
Acyl chloride
Ester -> Alcohol + Carboxylic acid
Reflux + dilute acid or alkali
Carboxylic acid -> Ester
Alcohol + acid catalyst
Acyl chloride -> Ester
Alcohol
Carboxylic acid -> Acyl chloride
PCl5
Acyl chloride -> Carboxylic acid
Cold H2O
Halogenoalkane -> Primary amine
Excess ammonia in ethanol + heat in sealed tube
Halogenoalkane -> Nitrile
KCN + Ethanol + Reflux
Halogenoalkane -> Carboxylic acid
Mg + dry ether (grignard)
Then + CO2 and dilute acid
Acyl chloride -> Primary amide
NH3
Acyl chloride -> Secondary amide
Primary amine
Acyl chloride -> Tertiary amide
Secondary amine
Nitrile -> Primary amine
LiAlH4 + dilute acid
Benzene -> Alkyl benzene
Halogenoalkane + AlCl3 catalyst + Reflux
Benzene -> Phenylketone
Acyl chloride + AlCl3 catalyst + Reflux
Benzene -> Nitrobenzene
Conc HNO3 + Conc H2SO4 catalyst
below 55C to stop further nitros from attaching
Nitrobenzene -> Phenylamine
Tin + Conc HCl + reflux
Then NaOH
Benzene -> Bromobenzene
Br2 + Iron filings
Benzene -> Halobenzene
X2 + Halogen carrier (e.g AlCl3)
Phenol + Bromine water ->
Tribromophenol
What are the four ways of extending the carbon chain?
- RX + KCN
- Friedel-Crafts
- HCN + Carbonyl
- Grignard
How can you use RX (halogenoalkane) and CN- to extend the carbon chain?
Use CH3Br as the halogenoalkane example
CH3Br + KCN -> CH3CN + KBr
What are the two types of Friedel-Crafts?
Alkylation
Acylation
How does alkylation work?
Benzene + Halogenoalkane (with AlCl3 catalyst) -> Alkylbenzene + HX
Use CH3Cl as the halogenoalkane example for Friedel-Crafts alkylation
Benzene + CH3Cl -> Methylbenzene + HCl
What does the reaction between HCN and carbonyls form?
Hydroxynitriles
CH3CHO + HCN ->
CH3CH(OH)CN 2-hydroxypropanenitrile
How do you make grignard reagents?
Halogenoalkane + Mg + Dry ether solvent + Reflux
CH3Br + Mg ->
CH3MgBr
CH3MgBr + H2O ->
CH3CH3
How do you get from grignard to carboxylic acid?
Grignard + CO2 Then hydrolysed (+ H2O) in the presence of dilute acid
How do you get from grignard to alcohol?
Grigard + Carbonyl Then hydrolysed (+ H2O) in the presence of dilute acid