3.3.14 Organic synthesis Flashcards
How do you produce a haloalkane from an alkane?
mechanism and conditions
Free radical substitution
Halogen and UV light
How do you produce an alcohol from a haloalkane?
mechanism and conditions
Nuc sub.
Warm aqueous NaOH, ethanol
How do you produce an amine from a haloalkane?
mechanism and conditions
Nuc sub
NH3 and heat
(excess if making primary amine)
How do you produce an alkene from a haloalkane?
mechanism and conditions
Elimination
Hot KOH, ethanol
How do you produce a nitrile from a haloalkane?
mechanism and conditions
Nuc sub
KCN with ethanol, heat
How do you produce an amine from a nitrile?
type of reaction and conditions
Reduction
LiAlH4, in dry ether
How do you produce an amide from an amine?
mechanism and conditions
Nuc add elim, acylation
Acid chloride/anhydride
How do you produce an alkene from an alcohol?
mechanism and conditions
Elimination
Dehydration
Conc H2SO4 at 180°C
How do you produce an aldehyde/ketone from an alcohol?
conditions
K2Cr2O7 and sulfuric acid
Heat and distill if primary alcohol/aldehyde
How do you produce an alkane from an alkene?
type of reaction and conditions
Reduction
H2 and Ni, 200°C
How do you produce an alcohol from an alkene?
conditions
Conc H3PO4
High temp, high pressure and steam
How do you produce an alkyl hydrogensulphate from an alkene?
mechanism and conditions
Elec add
Conc H2SO4
How do you produce a haloalkane from an alkene?
mechanism and conditions
Elec Add
HX (like HBr)
How do you produce an alcohol from an alkyl hydrogensulphate?
Dilute and warm
How do you produce a 2-hydroxynitrile from a ketone/aldehyde?
mechanism and conditions
Nuc add
KCN, followed by HCl (aq)
How do you produce an alcohol from an aldehyde/ketone?
mechanism and conditions
Nuc add
Reduction
NaBH4 (aq) and acidic solvent
How do you produce a carboxylic acid from an aldehyde?
reagents and conditions
K2Cr2O7 and H2SO4
heat
or Fehling’s solution/Tollen’s reagent
How do you produce an ester from a carboxylic acid and alcohol?
conditions
Conc H2SO4 catalyst
How do you produce a carboxylic acid and alcohol from an ester?
conditions
conc. H2SO4
How to produce cyclohexane from benzene?
type of reaction and conditions
Reduction
H2 and Ni catalyst
How do you produce nitrobenzene from benzene?
mechanism and conditions
Elec sub
Conc HNO3, conc H2SO4
How do you produce phenylamine from nitrobenzene?
type of reaction and conditions
Reduction
HCl and Sn, then NaOH
How do you produce an N-substituted phenylamide from phenylamine?
mechanism, type of reaction and conditions
Nuc add elim
Acylation
Acid chloride/anhydride
How do you produce benzaldehyde from benzene?
Elec sub
(Freidel crafts) acylation
Acid chloride/anhydride, AlCl3
How do you produce a benzyl alcohol from a benzaldehyde?
Nuc Add
NaBH4 (aq) and acidic solvent
