28 - Organic synthesis Flashcards
reagents for: Alkene to haloalkane
Hydrogen halide
RTP
addition
reagents for: alkene to primary alcohol
H20 (g) in the presence of phosphoric acid
addition
reagents for: primary alcohol to aldehyde
gentle heating with acidifies potassium dichromate (oxidation)
K2Cr3O7/H2SO4
distil the reaction
orange to green
reagents for: primary alcohol to carboxylic acid
heated strongly under reflux with excess K2Cr3O7/H2SO4
oxidation
reagents for: Primary alcohol to haloalkane
heat under reflux
H2SO4 and sodium halide
reagents for: secondary alcohol to ketone
K2Cr3O7/H2SO4
oxidation
reflux
reagents for: haloalkane to alkene
NaOH (aq)
reflux
reagents for: alkane to haloalkane
halogen/UV
substitution
reagents for: aldehyde toe carboxylic acid
reflux with acidified dichromate (VI) ions Cr2O7 3-/H+
K2Cr3O7/H2SO4
oxidation
reagents for: aldehydes to primary alcohols
NaBH4/H20
reduction
reagents for: ketone to secondary alcohol
NaBH4/H20
reduction
reagents for: aldehyde to hydroxyntrile
NaCN/H+
nucleophilic addition
alkene to haloalkane
REACTANTS: Alkene and Hydrogen Halide (HX) or X2
CONDITIONS: Hydrogen Halide Gas or (concentrated) Hydrohalide Acid or Halogen Liquid (pure Br2) or halogen Water (Br2(aq))
PRODUCT(S): Haloalkane
REACTION TYPE: Electrophilic Addition
alkene to alcohol
REACTANTS: Alkene and Steam (H2O(g))
CONDITIONS: Heat and Acid Catalyst (Phosphoric Acid,H3PO4)
PRODUCT(S): Alcohol
REACTION TYPE: Electrophilic Addition, (acid catalysed) Hydration
why do you use an acid catalyst in the hydration of an alkene
Acid catalyst is required to form hydroxonium ion (H3
O+) ion that is able to act as an electrophile to start the reaction.
how does an alkene react with Br2
Double bond in alkene polarises the bromine molecule to form an electrophile (Brδ+) that starts the
reaction.
how do you test for the presence of a carbon-carbon double bond
Reaction can be used to test for the presence of an alkene. A sample is mixed with bromine water, if
the bromine water turns colourless (from orange - brown) an alkene is present in the sample
alkene to alkane
REACTANTS: Alkene and Hydrogen, H2
CONDITIONS: Approximately 150oC and Nickel (solid) Catalyst
PRODUCT(S): Alkane
REACTION TYPE: Addition, Hydrogenation
nitriles to haloalkanes
- Sodium cyanide NaCN or potassium cyanide KCN
- in ethanol
- length of the chain is increased
aldehydes to nitriles
- reaction with hydrogen cyanide
- HCN is poisonous so a mixture of sodium cyanide and sulfuric acid
NaCN + H2SO4 -> HCN + Na2SO4
ketones to nitriles
nitriles to amines
- reduction reaction
- react with hydrogen with an acid catalyst
what does propanenitrile hydrogen and a nickel catalyst form
propylamine
- a reduction reaction
nitrile to carboxylic acid
react nitriles with dilute aqueous acid (HCl)and heat
- a hydrolysis reaction
how to form butanoic acid from a nitrile
butanenitrile and dilute aqueous acid like HCl
butanenitrile + H2O + HCl -> butanoic acid + ammonium chloride
what is alkylation (benzene)
- reaction that tranfers the alkyl group from haolalkane to benzene ring
- take place with AlCl3
benzene to ethylbenzene
react with AlCl3 and C2H5Cl chloroethane
- HCl is formed
acylation of benzene
- react with acyl chloride in the presence of aluminium chloride
