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Organic synthesis

CHEM2 and CHEM4 organic pathways
by

Jolene Taylor

on 20 December 2012

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Transcript of Organic synthesis

Alkene Alkane Dihaloalkane Alcohol Haloalkane Ketone Hydroxynitrile Aldehyde Carboxylic acid Nitrile Amine Acyl chloride N-substituted Amide Ester Amide Halogen (X )
room temp 2 Electrophilic addition H + Ni catalyst
high temp > 150oC 2 Reduction HX, room temp Elimination Electrophilic addition Dehydration Electrophilic
addition Free radical
Substitution Nucleophilic substitution Nucleophilic
addition-elimination Nucleophilic
addition-elimination Nucleophilic
addition-elimination Nucleophilic
addition-elimination Nucleophilic
addition-elimination Nucleophilic
substitution Nucleophilic substitution Reduction Reduction Oxidation Oxidation Oxidation Reduction Nucleophilic
addition Nucleophilic
addition Hydrolysis Esterification NaOH (ethanolic)
Heat / reflux H SO then
add H O 2 2 4 Conc. H SO
reflux 2 4 Electrophilic addition Alkene + Br 2 Halogen (X )
UV light 2 conc. NH
Heat in a sealed vessel 3 Potassium dichromate
H SO , reflux 2 4 Potassium dichromate
H SO , distillation Potassium dichromate
H SO , reflux 2 4 4 2 HCN (in situ)
KCN + H SO
room temp HCN (in situ)
KCN + H SO
room temp 2 2 4 4 NaBH
(selective reduction) H + Ni catalyst
high temp > 150oC H + Ni catalyst
high temp > 150oC Nucleophilic addition Nucleophilic addition 2 2 NaBH
(selective reduction) 4 4 Alcohol, reflux
conc. H SO (catalyst) 2 4 (Acid) H O, H SO , reflux
(Base) NaOH, heat 2 2 4 H O, room temp 2 Alcohol
room temp NH
room temp 3 Amine
room temp Acyl chloride
room temp NaOH (aq)
room temp KCN (ethanolic)
Heat / reflux H + Ni catalyst
high temp > 150oC OR LiAlH
(selective reduction) 2 4 Electrophilic addition Alkene + H SO 2 4 Electrophilic addition Alkene + HBr Free radical substitution Alkane + Cl 2 Oxidation of alcohols 1 alcohol --> aldehyde 1 alcohol --> carboxylic acid 2 alcohol --> ketone o o o CH CH OH + [O] --> CH CHO + H O CH CH OH + 2[O] --> CH COOH + H O CH CH(OH)CH + [O] --> CH COCH + H O 3 3 3 3 3 3 3 3 2 2 2 2 2 Reduction of aldehydes and ketones aldehyde --> 1 alcohol 2 alcohol --> ketone o o CH CHO + 2[H] --> CH CH OH CH COCH + 2[H] --> CH CH(OH)CH 3 3 3 3 3 3 2 2 2 CH CHO + H --> CH CH OH 3 3 2 CH COCH + H --> CH CH(OH)CH 3 3 3 3 Nucleophilic addition Aldehyde (or ketone) + H 2 Nucelophilic addition Aldehyde (or ketone) + HCN (in situ) Nucleophilic substitution Haloalkane + NaOH (aq) Nucleophilic substitution Haloalkane + KCN Elimination Haloalkane + NaOH
(ethanolic) Nucleophilic substitution Haloalkane + NH 3 Reduction of nitriles nitrile --> amine CH CN + 4[H] --> CH CH NH 3 3 2 2 2 CH CN + 2H --> CH CH NH 3 3 2 2 Nucleophilic addition-elimination Acyl chloride + H O 2 Nucleophilic addition-elimination Acyl chloride + alcohol Nucleophilic addition-elimination Acyl chloride + amine Nucleophilic addition-elimination Acyl chloride + NH 3 Esterification carboxylic acid + alcohol --> ester + water 3 CH COOH + CH OH <=> CH COOCH + H O 3 3 2 3 Esters can also be made by reacting alcohols with acyl chlorides or acid anhydrides, these reactions have a higher yield, do not require an acid catalyst and have a faster rate of reaction. + conc. sulphuric acid catalyst Hydrolysis of esters Acid hydrolysis 3 CH COOCH + H O --> CH COOH + CH OH 3 3 2 3 + dil. sulphuric acid catalyst Base hydrolysis CH COOCH + NaOH --> CH COONa + CH OH 3 3 3 3
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