chemistry - overview of aliphatic organic chemistry

OVERVIEW - ALIPHATIC ORGANIC CHEMISTRY

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Effect of NaOH(aq) on Phenol: ArOH(s) + NaOH(aq) → ArO–Na+(aq) + H2O(l) on Amine/Ammonium Salt + Warm: CH3NH3+(aq) + OH–(aq) → CH3NH2(g) + H2O(l) ArNH3+(aq) + OH–(aq) → ArNH2(l) + H2O(l) NH4+(aq) + OH–(aq) → NH3(g) + H2O(l) on Amide, heat strongly: CH3CON(CH3)2 + OH–(aq) → CH3COO– (aq) + NH(CH3)2 (g)

Amide

[R]

HCl(aq)

Amine [R]

NS excess conc NH3, sealed tube, ethanol, reflux

Acidification HCl(aq)

Basic hydrolysis NaOH(aq), heat

*cleaves double bond*

Alkoxide NS (SN1/SN2) KOH (aq), heat

(Alkyl Halides) Substitution Dry HX/ZnX2, reflux OR: SOCl2 (pyridine) OR: PX3 / PX5, reflux

EA HX(g)

Reduction H2/Ni

Elimination KOH (alc)

Acid-Metal Rxn Na(s)

Alcohol

Dehydration ex conc H2SO4, 170°C

Mild oxidation cold, alkaline KMnO4

EA X2/CCl4

C

Polymer Vicinal Dihalide

EA X2 (aq)

Halohydrin

Diol

R2

N

orange ppt

2,4-DNPH NA HCN with small amount of KCN/base

O 2N 2,4-DNPHydrazone

Fehling’s Solution RCHO + 2Cu2+ + 5OH– → RCOO– + Cu2O + 3H2O red ppt

Tollen’s Reagent RCHO + 2Ag(NH3)2+ + 3OH– → RCOO– + 2Ag + 2H2O + 4NH3 Important Distinguishing Tests

N

silver mirror

N

NO2

H O 2N

I2, OH- || H2O, I– 1222, 3433, 4655 CHI3 (yellow ppt)

NO2

H

H

Ketone

Iodoform

N

Aldehyde

Oxidation K2Cr2O7(aq)/H2SO4(aq) heat, immediate distilln [O]

H

R1

Hydrolysis water

[R]

EA cold, conc H2SO4

Alkene

Nucleophilic Acyl Substitution SOCl2 (pyridine) OR: PX3 / PX5, reflux

[R]

Iodoform Test I2(aq)/NaOH(aq) heat

Hydrolysis H2O, warm

Alcohol

Carboxylic Acid

[R]

Alkyl Hydrogensulphate(VI)

Strong oxidation hot, acidified KMnO4, heat Addition Polymerisation O2, heat

NS conc H2SO4, 140°C

Halogenoalkane

Alkane

Acidic hydrolysis HCl(aq), heat

Ether

Esterification Esterification conc H2SO4

Na(s)/NaOH(aq)/ Na2CO3(aq)

Nitrile

Acid Chloride

Ester

Acid Salt

NS / Step up Rxn KCN (alc), heat

FRS UV, X2

Nucleophilic Acyl Substn conc NH3/amine

2,4-DNPH

2,4-dinitrophenylhydrazone orange ppt

Cyanohydrin Acidic hydrolysis

Carboxylic Acid

[R]

Amine Basic hydrolysis

Acid Salt nh06