Synthetic Routes Flashcards
How can an alcohol be converted to an alkene?
Conc. H2SO4 (dehydrating agent)
Reflux
(Dehydration reaction)
How can an alkene be converted to an alcohol?
Add water with a H2SO4 catalyst
How can an alcohol be converted to a ketone?
K2Cr2O7/H2SO4
Reflux
How can a ketone be converted to an alcohol?
React with NaBH4
In methanol
How can an alcohol be converted to an aldehyde?
K2Cr2O7/H2SO4
Distillation
How can an aldehyde be converted to an alcohol?
React with NaBH4
In methanol
How can an aldehyde/ketone be converted to a hydroxynitrile?
React with KCN and dilute HCl
How can a nitrile group be converted to a carboxylic acid group?
Water and dilute HCl
Reflux
How can an alkene be converted to an alkane?
H2/Ni
200°C
High pressure
How can alkenes be produced from alkanes?
High temperature
High pressure
(Thermal cracking)
How can haloalkanes be made from alkanes?
X2
UV light
(Free radical-substitution)
How can an alkene be converted to a haloalkane?
HX/X2
How can an alkene be formed from a haloalkane?
NaOH
Ethanolic
Reflux
How can a haloalkane be converted to an amine?
NH3
Heat
How can a haloalkane be converted to a nitrile?
KCN
Reflux
Aqueous/ethanolic
How can a nitrile be converted to an amine?
H2/Ni
200°C
High pressure
How are esters formed?
Alcohol + carboxylic acid
(Conc.) H2SO4 catalyst
Heated
How are esters hydrolysed?
NaOH
Reflux
OR
H2O
(dil.) H2SO4
Reflux
How can an aldehyde be converted into a carboxylic acid?
K2Cr2O7/H2SO4
Reflux
How can a carboxylic acid be converted into an alcohol?
React with LiAlH4
In dry ethoxyethane
How can an acyl chloride/acid anyhydride be converted to an amide?
NH3
Room temperature
How can an acyl chloride/acid anyhydride be converted to an ester?
Alcohol
Room temperature
How can an acyl chloride/acid anyhydride be converted to a carboxylic acid?
H2O
Room Temperature
How can a haloalkane be converted to an alcohol?
NaOH
Aqueous
Heat
Reflux
How can benzene be converted to a phenylketone or phenyl aldehyde?
RCOCl + AlCl3
Reflux
Non aqueous
(Friedel-Crafts acylation)
How can benzene be converted to nitrobenzene?
Concentrated HNO3
Concentrated H2SO4
How can nitrobenzene be converted to a phenyl amine?
Tin + HCl
Reflux
Then
React with NaOH
How do NaBH4 and LiAlH4 act as reducing agents?
Provide hydride (H-) ions
H+ ions are provided by the solvent
Which bond(s) do NaBH4 and LiAlH4 not reduce?
NaBH4:
- COOH
- CN
Both:
- C=C
What are the four stages in the synthesis of chloroalkanes?
- Initiation
- Propagation 1
- Propagation 2
- Termination
When reacting a haloalkane with ammonia how can the yield of the following be increased:
- Primary amine
- Quaternary ammonium salt
- Excess ammonia
- Excess haloalkane
What are the advantages of using an acid anhydride over an acyl chloride?
- Less corrosive
- Less vulnerable to hydrolysis
- Less vigorous reaction (more controllable)
- Does not produce toxic/corrosive fumes (HCl)
- Less volatile
What is the advantage of using an acyl chloride over an acid anhydride?
More reactive