NCEA Level 3 Organic Chemistry Reaction Schemes

H2/Ni or H2/Pt and heat

Alkene → Alkane

Br2

Alkene → dibromoalkane

HX

Alkene → Haloalkane

H2O/H+ and heat

Alkene → Alcohol

X2/UV slow

Alkane → Haloalkane

NH3 warm

Haloalkane → Aminoalkane

KOH(alc) reflux

Haloalkane → Alkene

KOH(aq) reflux

Haloalkane → Alcohol

cH2SO4

Alcohol → Alkene

SOCl2 or PCl3 or PCl5 reflux

Alcohol → Haloalkane

Cr2O72-/H+ reflux

Secondary Alcohol → Keytone

Cr2O72-/H+ distilled

Primary Alcohol → Aldehyde

Cr2O72-/H+ reflux

Primary Alcohol → Carboxylic acid

NaBH4 or LiAlH4

Keytone → Secondary Alcohol

NaBH4 or LiAlH4

Aldehyde → Primary Alcohol

Cr2O72-/H+ reflux

Aldehyde → Carboxylic acid

SOCl2

Carboxylic acid → Acid chloride

Alcohol and cH2SO4

Carboxylic acid → Ester

Base eg. NH3(aq)

Carboxylic acid → Carboxylate salt

H2O/H+ (acid hydrolysis)

Ester → Carboxylic acid + Alcohol

OH-(aq) (base hydrolysis)

Ester → Carboxylate salt + Alcohol

NH3(alc)

Ester → Primary Amide

Alcohol

Acid chloride → Ester

H2O

Acid chloride → Carboxylic acid

NH3(alc)

Acid chloride → Primary amide

Primary amine(alc)

Acid chloride → Secondary amide

Secondary amine(alc)

Acid chloride → Tertiary amide

Dibromoalkane

Alkene + Br2

Alkane

Alkene + H2/Ni and heat

Alcohol

Alkene + H2O/H+ and heat

Haloalkane

Alkene + HX

Haloalkane

Alkane + X2/UV (slow)

Alkene

Haloalkane + KOH(alc) reflux

Aminoalkane

Haloalkane + NH3 warm

Alcohol

Haloalkane + KOH(aq) reflux

Haloalkane

Alcohol + SOCl2 or PCl3 or PCl5 reflux

Alkene

Alcohol + cH2SO4

Keytone

Secondary alcohol + Cr2O72-/H+ reflux

Carboxylic acid

Primary alcohol + Cr2O72-/H+ reflux

Aldehyde

Primary alcohol + Cr2O72-/H+ distilled

Ester

Alcohol + Carboxylic acid + cH2SO4

Secondary alcohol

Keytone + NaBH4 or LiAlH4

Primary alcohol

Aldehyde + NaBH4 or LiAlH4

Carboxylate salt

Carboxylic acid + Base(aq)

Acid chloride

Carboxylic acid + SOCl2

Carboxylic acid

Acid chloride + H2O

Ester

Acid chloride + alcohol

Primary Amide

Acid chloride + NH3(alc)

Secondary Amide

Acid chloride + primary amine(alc)

Alcohol + Carboxylic acid

Ester + H2O/H+ (acid hydrolysis)

Amide

Ester + NH3(alc)

Carboxylate salt + alcohol

Ester + dil.OH- (base hydrolysis)

MnO4-(aq)

Alkene → Diol

Diol

Alkene + MnO4-