Organic synthesis

Alkene → Haloalkane

* ELECTROPHILIC ADDITION
* HX / X2
* 20ºC

Alkene → Alkane

* HYDROGENATION (ADDITION)
* H2
* Ni catalyst
* 150ºC

Alkene → Alcohol

* HYDRATION (ELECTROPHILIC ADDITION)
* Steam
* H3PO4
* 300ºC
* 60atm

Haloalkane → Alkene

* ELIMINATION
* KOH in ethanol
* Heat under reflux

Alcohol → Alkene

* ELIMINATION (DEHYDRATION)
* Conc. H2SO4
* Heat

Alkane → Haloalkane

* FREE RADICAL SUBSTITUTION
* X2
* UV light

Haloalkane → Alcohol

* NUCLEOPHILIC SUBSTITUTION
* Warm aq. NaOH
* Reflux

Alcohol → Haloalkane

* NUCLEOPHILIC SUBSTITUTION
* NaX
* H2SO4
* 20ºC

Haloalkane → 1º amine

* NUCLEOPHILIC SUBSTITUTION
* NH3 in ethanol
* Heat

Haloalkane → Nitrile

* NUCLEOPHILIC SUBSTITUTION
* KCN in ethanol
* Reflux

Alcohol → Aldehyde

* OXIDATION
* 1º alcohol
* H2SO4 + K2Cr2O7
* Distillation

Alcohol → Aldehyde → Carboxylic acid

* OXIDATION
* 1º alcohol
* H2SO4 + K2Cr2O7
* Reflux

Alcohol → Ketone

* OXIDATION
* 2º alcohol
* K2Cr2O7
* Reflux

Aldehyde → Alcohol

* REDUCTION
* NaBH4 in methanol + water

Carboxylic acid → Aldehyde → Alcohol

* REDUCTION
* NaBH4 in methanol + water

Ketone → Alcohol

* REDUCTION
* NaBH4 in methanol + water

Nitrile/Hydroxynitrile → Amine

* REDUCTION
* H2
* Ni catalyst
* High T + P

Aldehyde/Ketone → Hydroxynitrile

* NUCLEOPHILIC ADDITION
* aq. KCN + H2SO4
* 20ºC

Carboxylic acid → Acyl chloride

* NUCLEOPHILIC ADDITION-ELIMINATION
* SOCl2

Acyl chloride → Carboxylic acid

* NUCLEOPHILIC ADDITION-ELIMINATION
* H2O
* 20ºC

Acyl chloride → 1º amide

* NUCLEOPHILIC ADDITION-ELIMINATION
* NH3
* 20ºC

Acyl chloride → 2º amide

* NUCLEOPHILIC ADDITION-ELIMINATION
* 1º amine
* 20ºC

Acyl chloride → Ester

* NUCLEOPHILIC ADDITION-ELIMINATION
* Alcohol
* 20ºC

Carboxylic acid → Ester

* ESTERIFICATION
* Alcohol
* conc. H2SO4
* Heat

Ester → Carboxylic acid

* HYDROLYSIS
* Dil. H2SO4
* Reflux

Ester → Carboxylate ion

* HYDROLYSIS
* Dil. NaOH
* Reflux