All Organic Chem Flashcards
Alkenes to Alcohols
Electrophilic Addition
A) Cold conc. H2SO4, followed by H2O and heat
B) H2O(g), heat in the presence of conc. H3PO4 catalyst at high temperature and pressure
Alkenes to Diols
Oxidation
Cold KMnO4 in KOH
Alkenes to CO2, H2O and Carbonyl compounds/ Carboxylic Acids
KMnO4 in H2SO4, heat under reflux
Alcohols to Alkenes
Elimination
1) Excess conc. H2SO4, heat
2) Conc. H3PO4, heat
3) Al2O3, heat
Halogenoalkanes to Alkenes
Elimination
KOH in ethanol, heat under reflux
Benzene to Halogenoarenes
Electrophilic Substitution
X2 with anydrous FeX3 or AlX3
Benzenes to Nitroarenes
Electrophilic Substitution
Conc. HNO3 and conc. H2SO4, heat under reflux at 55degC
Methylbenzenes to Nitromethylbenzenes
Conc. HNO3 and conc. H2SO4, 30degC
Benzenes to Alkylarenes
Ch3Cl with anhydrous FeCl3/AlCl3
What is that equation in the formation of nitrobenzenes from Benzenes? (HNO3 and H2SO4)
Reversible reaction, where products are NO2+ + HSO4- + H3O+
Methylbenzenes to benzoic acids
Side chain Oxidation
KMnO4 in dilute H2SO4(AQ), heat under reflux
Alcohols to Halogenoalkanes
Nucleophilic Substitution
1) HX(g), heat (anhydrous ZnCl2 catalyst used with HCl)
—–Product: H2O
2) PX3 (l or s), heat
—–Product: H3PO3
3) PCl5(s)
—–Product: POCl3 + HCl(g)
4) SOCl2 in pyridine, heat
—–Product: SO2(g), HCl(g)
Halogenoalkanes to Alcohols
Nucleophilic Substitution
NaOH/KOH, heat under reflux
Halogenoalkanes to Nitriles
Nucleophilic Substitution
KCN or NaCN in ethanol, heat under reflux
Nitriles to Carboxylic Acids
Acidic Hydrolysis
HCl, heat under reflux
Halogenoalkanes to Primary Amines
Excess NH3 in ethanol, heat in sealed tube
Nitriles to Carboxylate Salts
Alkaline Hydrolysis
NaOH, heat under reflux
Carbonyl Compounds -> Cyanohydrins
Nucleophilic Addition
1) HCN and trace amount of NaCN as catalyst, cold
2) HCN and trace amount of NaOH to generate catalyst in-situ, cold
Carboxylic Acids -> Acyl Chlorides
Nucleophilic Substitution
1) PX3 (l or s), heat
—–Product: H3PO3
2) PCl5(s)
—–Product: POCl3 + HCl (g)
3) SOCl2 in pyridine, heat
—–Product: SO2(g), HCl(g)
Acyl Chlorides to Carboxylic Acids
Hydrolysis
H2O
Carboxylic Acids to Esters
Condensation
Alcohol, conc. H2SO4 catalyst, heat under reflux
Acyl Chlorides to Esters
Condensation
1) Alcohol
2) Phenol, NaOH
Acyl Chlorides to Amides
Condensation
NH3(g) or RNH2
Esters to Carboxylic Acids/Salts and Alcohols
Hydrolysis
H2SO4/NaOH, heat under reflux
Nitrobenzenes to Phenylamines
Reduction
Sn in excesss conc. HCl, heat under reflux, followed by addition of NaOH
Amines to Amides
Condensation
Anhydrous acyl chloride
When to use SN1 mechanism (two-step)
There is a stable tertiary carbocation intermediate as electron-donating alkyl groups disperse the positive charge on the carbocation intermediate
When to use the SN2 mechanism
There are no, or only one alkyl group, allowing easy approach of the nucleophile
Equation for Iodoform test
RCOCH3 + 3I2 + 4NaOH → RCOONa+ + CHI3 +3NaI + 2H2O
Equation for Tollens’ test
Aldehyde + 2[Ag(NH3)2]+ + 3OH— → Carboxylate salt + 2Ag + 4NH3 + 2H2O
Equation for Fehling’s Test
Aldehyde + 2Cu2+ + 5OH— → Carboxylate salt + Cu2O + 3H2O
Primary alcohol to Aldehyde
K2Cr2O7 in dilute H2SO4, heat with immediate distillation