6.2.4 Carbon-carbon Bond Formation
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what are some of the different reactions that involve formation of C-C bond
nucleophilic substitution of haloalkanes with cyanide ions addition of hydrogen cyanide to form hydroxynitriles preparing amines from nitriles preparing carboxylic acids from nitriles friedel crafts alkylation friedel crafts acylation
nucleophilic substitution of haloalkanes with cyanide ions
haloalkane -> nitrile reagent: KCN dissolved in ethanol/water mixture conditions: heat under reflux mechanism: nucleophilic substitution type of reagent: nucleophile, CN-
what does the nucleophilic substitution of a haloalkane with cyanide ions d o
increases the length of the carbon chain
how do you name a nitrile
nitrile group must be at the end of the chain start from numbering chain at the C with the CN “butanenitrile”
addition of hydrogen cyanide to carbonyls to form hydroxynitriles
carbonyl -> hydroxynitrile reagent: sodium cyanide and dilute sulfuric acid conditions: room temperature and pressure mechanism: nucleophilic addition
what do the NaCN and H2SO4 provide in the addition of hydrogen cyanide reaction
CN- ions and H+ ions needed in the second step of the mechanism
why not HCN
toxic gas that is difficult to contain KCN and NaCN are toxic due to the cyanide ion
preparing amines from nitriles
reduce nitrile to amine LiAlH4 in ether or reducing with H2 using nickel catalyst
preparing carboxylic acids from nitriles
hydrolysing nitriles by reacting them with strong acids will produce a carboxylic acid hydrolysis reaction
friedel crafts alkylation
benzene -> alkylbenzene reagents: chloroalkane in the presence of anhydrous aluminium chloride catalyst conditions: heat under reflux mechanism: electrophilic substitution
friedel crafts acylation
benzene -> phenyl ketone reagents: acyl chloride in presence of anhydrous aluminium chloride catalyst conditions: heat under reflux (50 degrees) mechanism : electrophilic substitution