final reagent & catalyst

Carboxylic Acid

Synthesis

SOCl2

Carboxylic Acid

Alcoholysis

ROH, HCl

Carboxylic Acid

Aminolysis

NH3 / RNH2 / R2NH. /DCC

Carboxylic Acid

Reduction

LiAlH4, H3O

Carboxylic Acid

Acid Halide to Acid Anhydride

Acid Halide

Hydrolysis

H2O

Acid Halide

Alcoholysis

ROH, Pyridine

Acid Halide

Aminolysis

2NH3/RNH2/R2NH

Acid Halide

Grignards Reaction

2RMgX, H3O

Acid Halide

Reduction

LiAlH4, H3O+

Acid Anhydride

Hydrolysis

H2O

Acid Anhydride

Alcoholysis

ROH, Pyridine

Acid Anhydride

Aminolysis

NH3/RNH2/R2NH. in DCC

Acid Anhydride

Grignards Reaction

2RMgX, H3O+

Acid Anhydride

Reduction

LiAlH4/ H3O+

Ester

Hydrolysis

H2O

Ester

Aminolysis

NH3 / RNH2 / R2NH

Ester

Grignards Reaction

RMgX, H3O+

Ester

Reductions

LiAlH4/H3O

Amide

Reduction

LiAlH4, H3O+

Amide

Hydrolysis

H2O

Nitriles

Hydrolysis

H2O/ NaOH or H3O+

Nitriles

Grignards Reactions

RMgX, H3O+

Nitriles

Reduction

LiAlH4/H3O+

Ae

Alkynes

H20, H2SO4/HgSO4

Oxidation

Primary & Secondary Alcohol

KMnO4 / Acid

SN FC Acylation

Benzene

Acyl Halide + AlCl3 or AlBr3

An basic

aldehyde or ketone

+Nu[3] = Acid

An acidic

aldehyde or ketone

+Acid ⇄ +NuH

Alcohol Formation

An Reduction

Aldehyde & Ketone

NaBH4, ethanol/ H3O

Alcohol Formation

An Carbanion

Aldehyde & Ketone

RMgX, ether/ H3O

Hydrate Formation

Aldehyde & Ketone

H2O

Acetal Formation

Aldehyde & Ketone

ROH

Imine Formation

Aldehyde & Ketone

Amine

Conjugate An

unsaturated aldehyde & ketone

Nu, H3O

Oxidation

Alkyl Benzene

KMnO4, H+

Oxidation

Primary Alcohol & Aldehyde

KMnO4, H+

SN2

Haloalkane

NaCN

SN2

Nitrile

H2O/ NaOH or H3O

SR

X2 (Cl2 or Br2)/ hv or heat

X2 (Cl2 or Br2)/ hv or heat

SR

AE

• HX/ Ether

• X2/ DCM/CCl4

• HX/ Ether

• X2/ DCM/CCl4

AE

Bromination (Linear)

Br2, NBS/ hv/CCl4

Bromination (Cyclic)

Br2, NBS/ Ph(CO2)2/CCl4

SN1

HX/ Ether

HX/ Ether

SN1

SN2

• PBr3/ Ether

• SOCl2/ Pyridine

• PBr3/ Ether

• SOCl2/ Pyridine

SN2

Grignards Reagent (SN)- RX

Mg/ Ether / THF

Mg/ Ether / THF

Grignards Reagent (SN)- RX

Bimolecular Elimination (E2), Unimolecular Elimination (E1) & Unimolecular elimination conjugate base (E1cB)

KOH/ Ethanol

KOH/ Ethanol

Bimolecular Elimination (E2), Unimolecular Elimination (E1) & Unimolecular elimination conjugate base (E1cB)

AE Hydration Alkene/Alkynes

H20/H2SO4

SN Reactions Haloalkanes

H2O

Carbonyl Reduction

Aldehyde/Ketone

NaBH4, ethanol or water/ Weak acid (H3O+)

Carbonyl Reduction

Carboxylic Acid/ Ester

LiAlH4, ether/ Weak acid (H3O+)

Grignards Reaction RMgX

Carbonyl Groups

RMgX, ether/ Weak acid (H3O+)

Grignards Reaction RMgX

Carbonyl Groups; Ester

2RMgX, ether/ H3O+

E1 Dehydration of Alcohol

Secondary & Tertiary Alcohol

H2SO4/ H2O

Oxidation of Alcohol

Primary & Secondary Alcohol

CrO3/NaCr2O7/KMnO4

Periodinane/ DCM

SN2 Williamson’s Ether Rxn

NaX & RX

AE Alkenes

ROH/ H+

Peroxy Acids (mCPBA)

Acidic Ether Cleavage

HX (HBr or I)

Epoxide

HX

H3O+

Dow Process

Benzene

NaOH,H2O/35Odeg & H+

NaOH/H2O & NaOH/350deg & H+

Oxidation-Reduction

Phenols

Na2Cr2O7/ H3O & SnCl2, H2O

Oxidation-Reduction

Hydroquinone

Na2Cr2O7/H3O

SN1

Primary & Secondary Haloalkanes

Thiol ion (-SH)

SN 1

RSH (Oxidation)

RSH, I2 or Br2

SN1

Disulfides

Zn in CH3COOH

SN2 Sulfide Synthesis

Thiol

NaH & RI

SE Nitrobenzene Reduction

H2/ Pd

SN2 Reduction of Nitriles

NaCN to LiAlH4/ ether or H2O

SN Acyl of Carboxylic Acids and Derivatives and Reduction of Amides

• RCOOH

SOCl2 or DCC/ NH3 to LiAlH4/ ether/H2O

SN Acyl of Carboxylic Acids and Derivatives and Reduction of Amides

• RCOX

x’ss NH3, RNH2, R2NH in Pyridine to LiAlH4/ ether/H2O

SN Acyl of Carboxylic Acids and Derivatives and Reduction of Amides

• RCOOCOR

NH3, RNH2, R2NH in Pyridine to LiAlH4/ ether/H2O

SN2 Alkylation of RX and Amines

NH3, RNH2, R2NH, R3N/ NaOH

SN2 Alkylation of RX and Azide Ions (N3 -)

NaN3/ethanol to LiAlH4/ ether/H2O

Reductive Amination

NH3,RNH2,R2NH to H2 or Ni/ NaBH