reactions

haloalkane to alcohol

substitution, H2O or HO-

haloalkane to ether

ROH or RO-, substitution

Haloalkane to Amine (RNHR’ or R2NR’)

RNH2 or R2NH, substitution

haloalkane to thioether

substitution, RSH or RS-

haloalkane to nitrile R’CN

NaCN, KCN, or LiCN, substitution

haloalkane to alkane R’-R

substitution, Grignard reagent RMgX

Alcohol (R’OH) to haloalkane

HX or PX3, substitution

alcohol to tosylate R’OT then R’Nu

TsCl the Nu (nucleophile), substitution

aryl halide (ArX) to aryl amine (Ar-NHR)

NH2R, Pd catalyst, substitution

aryl halide to Ar-Ar’

substitution, Ar’-M (organometallc reagent, Pd catalyst)

Alkene to alkane

addition, H2, Pd/C catalyst

alkene to haloalkane

HX, addition

alkene to 1,2, - dihaloalkane

addition, X2

alkene to 1-Alkoxy-2-haloalkane

X2, ROH, addition

alkene to 1-hydroxy-2-haloalkane

X2, H2O, addition

alkene to alcohol (markovnikov)

H2O, H+ catalyst, addition

alkene to alcohol (anti-markovnikov)

addition, BH3, then H2O2, NaOH

alkyne to alkane

H2, Pd/C catalyst, addition

alkyne to alkene (Z)

addition, H2, Pd/PbSO4/CaCO3 catalyst

alkyne to 2,2-dihaloalkane

HX (2 equiv.) , addition

alkyne to 1,1,2,2,-tetrahaloalkane

X2 (2 equiv.) , addition

alkyne to ketone

H2O, HgSO4, H+ catalyst, addition

aldehyde to alcohol (Secondary)

addition, Grignard reagent RMgX, then H3O+

aldehyde to alcohol (primary)

NaBH4, then H3O+, addition

ketone to alcohol (tertairy)

addition, Grignard reagent RMgX, then H3O+

ketone to alcohol (secondary)

addition, NaBH4, then H3O+

CO2 to carboxylic acid

addition, Grignard reagent RMgX, then H3O+

nitrile to carboxylic acid

addition, NaOH

nitrile to amine

addition, LiAlH4

carboxylic acid to alcohol

addition, LiAlH4

acid chloride to alcohol

addition, LiAlH4

ester to alcohol

addition, LiAlH4

amide to amine

addition, LiAlH4

alcohol to alkene

H+, Δ, elimination

haloalkane to alkene

Base, Δ, elimination

amide to nitrile

P2O5, elimination

alcohol (primary) to carboxylic acid

KMnO4, or CrO3, or K2Cr2O7,

• redox (oxidation)

alcohol (primary) to aldehyde

PCC, or Oxidoreductase and NAD+/NADP+,

• redox (oxidation)

alcohol (secondary) to ketone

KMnO4, or CrO3, or K2Cr2O7, or PCC

Oxidoreductase and NAD+/NADP

• redox (oxidation)

aldehyde to carboxylic acid

KMnO4, or CrO3, or K2Cr2O7,

• redox (oxidation)

aldehyde to alcohol (primary)

NaBH4, LiAlH4, Enzyme and NADH/NADPH

• redox (reduction)

ketone to alcohol (secondary)

NaBH4, LiAlH4, Enzyme and NADH/NADPH

• redox (reduction)

carboxylic acid to alcohol (primary)

LiAlH4

• redox (reduction)

ester to alcohol (primary)

LiAlH4

• redox (reduction)

amide to amine

LiAlH4

• redox (reduction)

nitrile to amine (primary)

LiAlH4

• redox (reduction)