OCR A 6.2.4 Carbon Carbon Bond Formation

extending C chain

-uses C-C bond formation

-carbon chains cant be added tgthr in their simple hydrocarbon form

-issue as extending C chain to synthesis organic products is important

-we use reactants and reagents that have C atom which acts as nucleophile/electrophile

cyanide

-negatively charged atom

-nucleophile

cyanide w/ haloalkane

-halogen more electronegative than C; pull e towards themselves in covalent bond; polar bond

-C ca be attached by cyanide nucleophile

-extend C chain as -CN substitutes halogen

-produces C-C bond between d+ C and C on cyanide

haloalkane reaction w/ cyanide

-make nitrile

-nucleophilic substitution

-conditions; warm ethanoic potassium cyanide, under reflux

-nucleophile attacks d+ C and replaced halogen

-C-X breaks, both e move from bond to halogen

-new bond formed between CN ion and C

cyanide mechanism reaction w/ ethane

KCN reaction w/ carbonyl compound

-produces hydroxynitrile

-mixture of KCN and H₂SO₄ used

-nucleophilic addition

-CN- ion attacks d+ C; lone pair of e donated from CN ion

-2 e in dbl bond transferred to O

-as KCN is acidified there is supply of H+ ion in sol

-H+ ion accept lone pair of e from O

why HCN not used

-too poisonous

how to make amine

-reduce nitrile using H₂ gas and Ni/Pt catalyst used, w/ high temp and pressure

hydrolysis of nitriles

-form carboxylic acids by heating w/ dilute aq acid (HCl)

alkylation

-reaction that transfers an alkyl group from haloalkane to benzene ring

-AlCl₃ catalyst

acylation

-when benzene reacts w/ acyl chloride to form ketone

-AlCl₃ catalyst