SUMMARY OF ORGANIC REACTIONS wSUMMARY OF ORGANIC REACTIONS
SECTION 1 - ALIPHATIC
Aldehydes and ketones
Type of reaction
Mechanism
1. oxidation (aldehydes only): aldehyde ( carboxylic acid
reagents: potassium dichromate (K2Cr2O7) in sulphuric acid (H2SO4)
conditions: warm under reflu...
wSUMMARY OF ORGANIC REACTIONS
SECTION 1 - ALIPHATIC
Aldehydes and ketones
Type of reaction
Mechanism
1. oxidation (aldehydes only): aldehyde ( carboxylic acid
reagents: potassium dichromate (K2Cr2O7) in sulphuric acid (H2SO4)
conditions: warm under reflux
equation: R-CHO + [O] ( R-COOH
observation: orange to green
to distinguish between aldehydes and ketones:
either:
add Fehling’s solution and heat
observation: blue solution to brick red precipitate
equation: R-CHO + 4OH- + 2Cu2+ ( R-COOH + Cu2O + 2H2O
or:
add Tollen’s reagent and heat
observation: colourless solution to silver mirror
equation: R-CHO + 2[Ag(NH3)2]+ + H2O ( RCOOH + 2Ag + 4NH3 + 2H+
n/a
2. reduction: carbonyl ( alcohol
reagents: NaBH4(aq)
conditions: room temperature
equation: R1-CO-R2 + 2[H] ( R1-CH(OH)-R2
Nucleophilic addition (required)
3. addition of HCN: carbonyl ( hydroxynitrile
reagents: NaCN and HCl(aq)
conditions: room temperature
equation: R1-CO-R2 + HCN ( R1-C(CN)(OH)-R2
Nucleophilic addition (required)
Carboxylic acids and their salts
Type of reaction
Mechanism
1. acid-base
a) carboxylic acids with sodium hydroxide
reagent: NaOH
conditions: room temperature
equation: R-COOH(aq) + NaOH(aq) ( R-COO-Na+(aq) + H2O(l)
b) carboxylic acids with sodium carbonate
reagent: Na2CO3
conditions: room temperature
equation: 2R-COOH(aq) + Na2CO3(aq) ( 2R-COO-Na+(aq) + CO2(g) + H2O(l)
observations: colourless gas evolved which turns limewater milky
c) carboxylate salts with acids
reagent: HCl(aq)
conditions: room temperature
equation: R-COO-(aq) + H+(aq) ( R-COOH(aq)
n/a
2. esterification
reagents: any alcohol, concentrated sulphuric acid catalyst
conditions: heat and reflux
equation: R1-COOH + R2OH == R1-COOR2 + H2O
Nucleophilic addition/
Elimination
(not required)
Esters
Type of reaction
Mechanism
hydrolysis
a) acid hydrolysis
reagent: concentrated H2SO4
conditions: heat under reflux
equation: R1-COOR2 + H2O == R1-COOH + R2OH
b) alkaline hydrolysis (saponification)
reagent: NaOH(aq)
conditions: heat under reflux
equation: R1-COOR2 + NaOH == R1-COO-Na+ + R2OH
n/a
Acyl chlorides and acid anhydrides
Type of reaction
Mechanism
1. acylation using acyl chlorides
a) with water (to make carboxylic acids)
conditions: room temperature
equation: R-COCl + H2O ( R-COOH + HCl
observation: white misty fumes
b) with ammonia (to make amides)
conditions: room temperature
equation: R-COCl + NH3 ( R-CONH2 + HCl
observation: white misty fumes
c) with alcohols (to make esters)
conditions: room temperature
equation: R1-COCl + R2-OH ( R1-COOR2 + HCl
observation: white misty fumes
d) with primary amines (to make N-substituted amides)
conditions: room temperature
equation: R1-COCl + R2-NH2 ( R1-CONHR2 + HCl
observation: white misty fumes
Nucleophilic addition-elimination
(required)
2. acylation using acid anhydrides
a) with water (to make carboxylic acids)
conditions: room temperature
equation: R1-COOCO-R2 + H2O ( R1-COOH + R2-COOH
observation: white misty fumes
b) with ammonia (to make amides)
conditions: room temperature
equation: R1-COOCO-R2 + NH3 ( R1-CONH2 + R2-COOH
observation: white misty fumes
c) with alcohols (to make esters)
conditions: room temperature
equation: R1-COOCO-R2 + R3-OH ( R1-COO-R3 + R2-COOH
observation: white misty fumes
d) with primary amines (to make N-substituted amides)
conditions: room temperature
equation: R1-COOCO-R2 + R3-NH2 ( R1-CONH-R3 + R2-COOH
observation: white misty fumes
Nucleophilic addition-elimination
(not required)
Amines
Type of reaction
Mechanism
1. haloalkane ( primary amine
reagents: haloalkane and excess ammonia
conditions: heat
equation: R-X + 2NH3 ( R-NH2 + NH4X
or
reagent: haloalkane and ammonia (1:1 ratio)
conditions: heat
equation: R-X + NH3 ( R-NH2 + HX
2. haloalkane ( secondary amine
reagents: haloalkane and ammonia (2:1 ratio)
conditions: heat
equation: 2R-X + NH3 ( R-NH-R + HX
or
reagents: haloalkane and primary amine
conditions: heat
equation: R1-X + R2-NH2 ( R1-NH-R2 + HX
3. haloalkane ( tertiary amine
reagents: haloalkane and ammonia (3:1 ratio)
conditions: heat
equation: 3R-X + NH3 ( R3N + HX
or
reagents: haloalkane and secondary amine
conditions: heat
equation: R1-X + R2-NH-R3 ( R1R2R3N + HX
4. haloalkane ( quartenary ammonium salt
reagents: haloalkane and ammonia (4:1 ratio)
conditions: heat
equation:
4R-X + NH3 ( [R4N]+X-
or
reagents: haloalkane and secondary amine
conditions: heat
equation: R1-X + R2R3R4N ( [R1R2R3R4N]+X-
Nucleophilic substitution (required)
2. reduction: nitrile ( primary amine
reagents: LiAlH4 in dry ether
conditions: room temperature
equation: R-CN + 4[H] ( R-CH2NH2
n/a
3. acid-base:
a) amines with acids
equations: R1-NH2 + HCl ( R1-NH3Cl
R1R2-NH + HCl ( R1R2-NH2Cl
R1R2R3-N + HCl ( R1R2R3-NHCl
b) alkyl ammonium salts with alkalis
equations: R1-NH3Cl + NaOH ( R1-NH2 + NaCl + H2O
R1R2-NH2Cl + NaOH ( R1R2-NH + NaCl + H2O
R1R2R3-NHCl + NaOH ( R1R2R3-N + NaCl + H2O
n/a
Amino Acids
Type of reaction
Mechanism
1. acid-base reactions of amino acids
a) with acids
reagents: HCl
conditions: room temperature
equation: R-CH(NH2)-COOH + HCl ( R-CH(NH3+Cl-)-COOH
b) with alkalis
reagents: NaOH
conditions: room temperature
equation: R-CH(NH2)-COOH + NaOH (R-CH(NH2)-COO-Na+ + H2O
2. condensation reactions of amino acids
conditions: DNA
equation: n R-CH(NH2)-COOH ( H-(NHCRHCO)n-OH + (n-1) H2O
3. hydrolysis of proteins
reagents: 6 moldm-3 HCl
conditions: heat, reflux
equation: H-(NHCRHCO)n-OH + (n-1) H2O + n HCl ( n R-CH(NH3+Cl-)-COOH
Nucleophilic addition-elimination
(not required)
Polymers
Type of reaction
Mechanism
1. Addition polymerisation (alkenes ( polyalkenes)
conditions: high temperature, Ziegle-Natte catalyst
equation:
2. Condensation polymerisation
a) polyesters
dicarboxylic acid + diol ( polyester
conditions: H2SO4, heat under reflux
equation:
or
diacyl chloride + diol ( polyester
conditions: room temperature
equation:
b) polyamides
dicarboxylic acid + diamine ( polyamide
conditions: warm, reflux
equation:
or
diacyl chloride + diamine ( polyamide
conditions: room temperature
equation:
Free radical addition
(not required)
Nucleophilic addition-elimination
(not required)
3. Hydrolysis of condensation polymers
a) polyesters
reagents: NaOH(aq)
conditions: heat
equation:
b) polyamides
reagents: HCl(aq)
conditions: heat
equation:
n/a
n/a
SECTION 2 – AROMATIC
Type of reaction
Mechanism
1. nitration (benzene ( nitrobenzene)
Reagent: conc HNO3 in conc H2SO4
Conditions: 50-55oC under reflux
Equation: C6H6 + HNO3 ( C6H5NO2 + H2O
Electrophilic substitution
(required)
2. alkylation (benzene ( alkylbenzene)
Reagent: R-Cl with anyhdrous AlCl3
Conditions: 50oC under reflux
Equation: C6H6 + R-Cl ( C6H5-R + HCl
OR
Reagent: alkene with anhydrous AlCl3 and HCl
Equation: C6H6 + R1R2C=CR1R2 ( C6H5CR1R2CR3R4
Electrophilic substitution
(required)
3. acylation (benzene ( phenylketone)
Reagent: R-COCl with anydrous AlCl3
Conditions: 50oC under reflux
Equation: C6H6 + R-COCl ( C6H5COR + HCl
Electrophilic substitution
(required)
4. reduction (nitrobenzene ( phenylamine)
Reagents: Sn in conc HCl
Conditions: heat under reflux
Equation: C6H5NO2 + 6[H] ( C6H5NH2 + 2H2O
n/a
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