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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:
Amide Nucleophilic Acyl Substn
conc NH3/amine
CH3NH3+(aq) + OH–(aq) → CH3NH2(g) + H2O(l) [R]
ArNH3+(aq) + OH–(aq) → ArNH2(l) + H2O(l)
NH4+(aq) + OH–(aq) → NH3(g) + H2O(l) Acid Chloride
on Amide, heat strongly: HCl(aq) Acid Salt Ester Esterification
CH3CON(CH3)2 + OH–(aq) → Amine Acidification
CH3COO– (aq) + NH(CH3)2 (g) Basic hydrolysis HCl(aq)
[R] NaOH(aq), heat Esterification
Na(s)/NaOH(aq)/ conc H2SO4
Na2CO3(aq) Alcohol Nucleophilic
NS
excess conc NH3, Nitrile Acyl Substitution
SOCl2 (pyridine)
sealed tube, ethanol, reflux Acidic hydrolysis OR: PX3 / PX5, reflux
Ether
NS / Step up Rxn
KCN (alc), heat NS
HCl(aq), heat
Carboxylic Acid
conc H2SO4, 140°C
Hydrolysis
[R] water
FRS Halogenoalkane Alkoxide
[R]
UV, X2 (Alkyl Halides) NS (SN1/SN2)
Acid-Metal Rxn
Substitution
KOH (aq), heat
Na(s) Oxidation Aldehyde
Dry HX/ZnX2, reflux K2Cr2O7(aq)/H2SO4(aq)
heat, immediate distilln
Alkane OR: SOCl2 (pyridine)
OR: PX3 / PX5, reflux Alcohol [O]
H H

EA [R] N N NO2
*cleaves Elimination
double HX(g) KOH (alc)
Dehydration
Ketone H

Reduction O 2N
bond* ex conc H2SO4, 170°C Hydrolysis Iodoform Test
H2/Ni I2(aq)/NaOH(aq) 2,4-DNPH
H2O, warm 2,4-DNPH
heat
Strong oxidation Alkyl Hydrogensulphate(VI) NA
hot, acidified KMnO4, heat HCN with
small amount of 2,4-dinitrophenylhydrazone
EA
Addition Polymerisation
Alkene cold, conc H2SO4 KCN/base orange ppt

O2, heat
Mild oxidation
EA
X2/CCl4 cold, alkaline KMnO4 R1 H Iodoform Cyanohydrin
I2, OH- || H2O, I–
C N N NO2
Acidic hydrolysis [R]
1222, 3433, 4655
Polymer Diol R2 orange ppt
CHI3 (yellow ppt)
EA O 2N 2,4-DNPHydrazone Amine
Vicinal Dihalide X2 (aq) Fehling’s Solution Carboxylic Acid Basic hydrolysis
RCHO + 2Cu2+ + 5OH– → RCOO– + Cu2O + 3H2O
red ppt
Halohydrin Acid Salt
Tollen’s Reagent
RCHO + 2Ag(NH3)2+ + 3OH– → RCOO– + 2Ag + 2H2O + 4NH3
silver mirror nh06
Important Distinguishing Tests