Synthetic Routes
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Alkane to haloalkane
Free radical substitution Br2, Cl2, etc UV light
Haloalkane to alcohol
Nucleophilic substitution Aqueous KOH or NaOH Heat under reflux
Haloalkane to nitrile
Nucleophilic substitution Heat under reflux with KCN dissolved in ethanol
Haloalkane to primary amine to secondary amine
Nucleophilic substitution Heat under reflux with (excess) NH3 dissolved in alcohol
Haloalkane to alkene
Elimination Heat under reflux with ethanolic KOH
Alkene to polyalkene
High pressure Catalyst
Alkene to haloalkane
Electrophilic addition HCl, HBr Room temp
Alkene to dihalogenoalkane
Electrophilic addition Cl2, Br2 Room temp
Dihalogenoalkane to diol
Nucleophilic substitution Aqueous KOH Heat under reflux
Alcohol to alkene
conc. H2SO4 or conc. H3PO4 Elimination, dehydration
Alkene to alcohol
Step 1: Electrophilic addition with H2SO4 Step 2: H2O warm hydrolysis
partial oxidation of primary alcohol
acidified potassium dichromate (VI) solution heat and distill aldehyde forms
complete oxidation of primary alcohol
acidified potassium dichromate (VI) solution heat under reflux carboxylic acid forms
oxidation of secondary alcohol
heat with acidified potassium dichromate (VI) solution forms ketone
why can’t tertiary alcohols not be oxidised
there is no H atom attached to the carbon with the -OH group
aldehyde to alcohol what type of alcohol forms
reduction with sodium borohydride (NaBH4) nucleophilic addition primary alcohol
ketone to alcohol what type of alcohol forms
reduction with sodium borohydride (NaBH4) nucleophilic addition secondary alcohol
alcohol to ester
carboxylic acid conc H2SO4 catalyst HCl gas used if benzene ring present
aldehyde to hydroxynitrile why does this form enantiomers
nucleophilic adition NaCN and H2SO4 Chiral carbon and planar C=O bond
Name the mechanism and reagent for ketone to hydroxynitrile when/why would this form enantiomers?
nucleophilic addition KCN If the ketone is asymmetrical, the C=O bond is planar and can be attacked by the nucleophile from either side
carboxylic acid to ester
heat with alcohol in the presence of H2SO4 catalyst Esterification
Acyl chloride/acid anhydride to ester
alcohol room temp nucleophilic addition-elimination
Acyl chloride/acid anhydride to carboxylic acid
H2O room temp nucleophilic addition-elimination
Acyl chloride/acid anhydride to secondary amide
primary amine room temp nucleophilic addition-elimination