All Organic Chem

Question 1

Alkenes to Alcohols

Answer 1

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

Question 2

Alkenes to Diols

Answer 2

Oxidation
Cold KMnO4 in KOH

Question 3

Alkenes to CO2, H2O and Carbonyl compounds/ Carboxylic Acids

Answer 3

KMnO4 in H2SO4, heat under reflux

Question 4

Alcohols to Alkenes

Answer 4

Elimination
1) Excess conc. H2SO4, heat
2) Conc. H3PO4, heat
3) Al2O3, heat

Question 5

Halogenoalkanes to Alkenes

Answer 5

Elimination
KOH in ethanol, heat under reflux

Question 6

Benzene to Halogenoarenes

Answer 6

Electrophilic Substitution
X2 with anydrous FeX3 or AlX3

Question 7

Benzenes to Nitroarenes

Answer 7

Electrophilic Substitution
Conc. HNO3 and conc. H2SO4, heat under reflux at 55degC

Question 8

Methylbenzenes to Nitromethylbenzenes

Answer 8

Conc. HNO3 and conc. H2SO4, 30degC

Question 9

Benzenes to Alkylarenes

Answer 9

Ch3Cl with anhydrous FeCl3/AlCl3

Question 10

What is that equation in the formation of nitrobenzenes from Benzenes? (HNO3 and H2SO4)

Answer 10

Reversible reaction, where products are NO2+ + HSO4- + H3O+

Question 11

Methylbenzenes to benzoic acids

Answer 11

Side chain Oxidation
KMnO4 in dilute H2SO4(AQ), heat under reflux

Question 12

Alcohols to Halogenoalkanes

Answer 12

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)

Question 13

Halogenoalkanes to Alcohols

Answer 13

Nucleophilic Substitution
NaOH/KOH, heat under reflux

Question 14

Halogenoalkanes to Nitriles

Answer 14

Nucleophilic Substitution
KCN or NaCN in ethanol, heat under reflux

Question 15

Nitriles to Carboxylic Acids

Answer 15

Acidic Hydrolysis
HCl, heat under reflux

Question 16

Halogenoalkanes to Primary Amines

Answer 16

Excess NH3 in ethanol, heat in sealed tube

Question 17

Nitriles to Carboxylate Salts

Answer 17

Alkaline Hydrolysis
NaOH, heat under reflux

Question 18

Carbonyl Compounds -> Cyanohydrins

Answer 18

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

Question 19

Carboxylic Acids -> Acyl Chlorides

Answer 19

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)

Question 20

Acyl Chlorides to Carboxylic Acids

Answer 20

Hydrolysis
H2O

Question 21

Carboxylic Acids to Esters

Answer 21

Condensation
Alcohol, conc. H2SO4 catalyst, heat under reflux

Question 22

Acyl Chlorides to Esters

Answer 22

Condensation
1) Alcohol
2) Phenol, NaOH

Question 23

Acyl Chlorides to Amides

Answer 23

Condensation
NH3(g) or RNH2

Question 24

Esters to Carboxylic Acids/Salts and Alcohols

Answer 24

Hydrolysis
H2SO4/NaOH, heat under reflux

Question 25

Nitrobenzenes to Phenylamines

Answer 25

Reduction
Sn in excesss conc. HCl, heat under reflux, followed by addition of NaOH

Question 26

Amines to Amides

Answer 26

Condensation
Anhydrous acyl chloride

Question 27

When to use SN1 mechanism (two-step)

Answer 27

There is a stable tertiary carbocation intermediate as electron-donating alkyl groups disperse the positive charge on the carbocation intermediate

Question 28

When to use the SN2 mechanism

Answer 28

There are no, or only one alkyl group, allowing easy approach of the nucleophile

Question 29

Equation for Iodoform test

Answer 29

RCOCH3 + 3I2 + 4NaOH → RCOONa+ + CHI3 +3NaI + 2H2O

Question 30

Equation for Tollens’ test

Answer 30

Aldehyde + 2[Ag(NH3)2]+ + 3OH— → Carboxylate salt + 2Ag + 4NH3 + 2H2O

Question 31

Equation for Fehling’s Test

Answer 31

Aldehyde + 2Cu2+ + 5OH— → Carboxylate salt + Cu2O + 3H2O

Question 32

Primary alcohol to Aldehyde

Answer 32

K2Cr2O7 in dilute H2SO4, heat with immediate distillation