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Class Functionalgp Suffix Example Formula
Alkane C - C - ane ethane CnH2n+2
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H H
H
‫׀‬
H - C – H
‫׀‬
H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Number
carbon
Word IUPAC
name
Structure formula Molecular
formula
1 Meth Methane CH4 CH4
2 Eth Ethane CH3CH3 C2H6
3 Prop Propane CH3CH2CH3 C3H8
4 But Butane CH3(CH2)2CH3 C4H10
5 Pent Pentane CH3(CH2)3CH3 C5H12
6 Hex Hexane CH3(CH2)4CH3 C6H14
7 Hept Heptane CH3(CH2)5CH3 C7H16
8 Oct Octane CH3(CH2)6CH3 C8H18
9 Non Nonane CH3(CH2)7CH3 C9H20
10 Dec Decane CH3(CH2)8CH3 C10H22
methane ethane propane butane
Saturated hydrocarbon (C – C single bond)
Chemical rxn AlkaneReactivityfor Alkanes
Combustion rxn
Complete combustion – produce CO2 + H2O
• C2H6 + 7/2O2 → 2CO2 + 3H2O
Incomplete combustion – produce C, CO, CO2, H2O
• 2C3H8 + 7O2 → 2C + 2CO + 8H2O + 2CO2
Free Radical Substitution rxn
Free Radical Substitution Mechanism
- Homolytic fission- bond break by radical form.
- Covalent bond split, each atom obtain one electron (unpair e)
- UV needed
- Radical react with molecule
- Radical + radical → molecule
CH4 + CI2 → CH3CI + HCI
• Low reactivity - Strongstable bondbet C - C, C - H
• Low reactivity - Low polarity of C - H bond
• Saturatedhydrocarbon – Non polarbond
Initiation
Propagation
Radical (dot)
Termination
homolytic
fission
Radical recycle again
1
2
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
C = C – C - H
‫׀‬ ‫׀‬
H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C = C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Unsaturated hydrocarbon (C = C double bond)
H H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C = C – C – C – C - H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
ethene propene butene pentene
Reactivityfor Alkene
- High reactivity - Unstable bondbet C = C
- High reactivity – Weak pi bond overlapbet p orbital
- Unsaturated hydrocarbon – ᴨ bondoverlap
Combustion rxn
Chemicalrxn Alkane
Complete combustion – produce CO2 + H2O
C2H4 + 3O2 → 2CO2 + 2H2O
Incomplete combustion – produce C, CO, CO2, H2O
2C2H4 + 7/2O2 → 2C + CO + 4H2O + CO2
CH2 = CH2 + Br2 → CH2BrCH2Br
CH2 = CH2 + HCI → CH3CH2CI
CH2 = CH2 + H2O → CH3CH2OH
Addition rxn
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
CI CI
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
Br Br
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H CI
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H OH
1
2
Polymerization(Additionrxn)3
Polymers are long chains molecules (plastics)
• Join repeat units call monomers
• Addition and condensation polymerization
• Monomers double bond (unsaturated)
• Repeat units join together by covalent bond without loss of any molecule
ethene polyethene
add monomer
polymer
propene polypropylene
add monomer
H CH3 H CH3
monomer
monomer
chloroethene polychloroethene
(PVC)
tetrafluoroethene polytetrafluoroethene
(PTFE)
H CI H CI
F F
F F
F F
F F
polymerization
polymer
Alkene decolourize
brown liq Br2
Class Functional Suffix Example Formula
Alkene Alkenyl - ene ethene CnH2n
OH
‫׀‬
CH3-C– CH3 + [O] No product
‫׀‬
CH3
OH O
‫׀‬ ‖
CH3- C–CH3 + [O] CH3- C – CH3 + H2O
H
‫׀‬
CH3 – C – OH
‫׀‬
H
Class Functional Suffix Example Formula
Alcohol Hydroxyl - ol methanol CnH2n+1OH
Number
carbon
IUPAC name Structure formula Molecular
formula
1 Methanol CH3OH CH3OH
2 Ethanol CH3CH2OH C2H5OH
3 Propanol CH3CH2CH2OH C3H7OH
4 Butanol CH3(CH2)2CH2OH C4H9OH
methanol ethanol propanol butanol
H
‫׀‬
H - C – OH
‫׀‬
H
H H
‫׀‬ ‫׀‬
H - C – C – OH
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬
H H H
H H H H
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – C – OH
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
H H H H
Hydrocarbon skeleton Functional gp
Chemical rxn AlcoholReactivityfor Alcohol
Primary 1 0
1 alkyl /R gp bond to C attach to OH
CH3 H
‫׀‬ ‫׀‬
CH3 – C – C – OH
‫׀‬ ‫׀‬
CH3 H
Combustionrxn
Complete combustion–produceCO2 + H2O
C2H6OH + 3O2 → 2CO2 + 3H2O
Incomplete combustion-produceC, CO, CO2, + H2O
2C2H5OH + 4O2 → C + 2CO + 6H2O + CO2
Oxidation rxn
Secondary 2 0
2 alkyl/R gp bond to C attach to OH
H
‫׀‬
CH3 – C – OH
‫׀‬
CH3
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H OH H
Tertiary 3 0
3 alkyl/R gp bond to C attach to OH
CH3
‫׀‬
CH3 – C – OH
‫׀‬
CH3
R
‫׀‬
R – C – OH
‫׀‬
R
H
‫׀‬
CH3-CH2-OH + [O] CH3- C = O + H2O
MnO4
-
/H+
K2Cr2O7/H+
Primary 10
– Oxidised to Aldehyde and Carboxylic acid
H OH
‫׀‬ ‫׀‬
CH3- C= O + [O] CH3-C=O
Secondary 20
- Oxidised to Ketone
Tertiary 30
- Cannot be Oxidised
MnO4
-
/H+
K2Cr2O7/H+
MnO4
-
/H+
K2Cr2O7/H+
MnO4
-
/H+
K2Cr2O7/H+
1
1
Esterificationrxn3
O H
‖ ‫׀‬
H - C – O – C – H + H2O
‫׀‬
H
H
‫׀‬
H- O – C – H
‫׀‬
H
O
‖
H - C – O-H +
Chemical rxn Alcohol
Oxidation rxn – oxidized carbon attach to OH
Primary 10
– Oxidised to Aldehyde and Carboxylic acid
Secondary 20
- Oxidised to Ketone Tertiary 30
- Cannot be Oxidised
OH
‫׀‬
CH3-C– CH3 + [O] No product
‫׀‬
CH3
MnO4
-
/H+
K2Cr2O7/H+
MnO4
-
/H+
K2Cr2O7/H+
MnO4
-
/H+
K2Cr2O7/H+
Alcohol to Aldehyde (Distillation)
1. Acidified dichromate(VI)/permanganate(VII)
2.Warm it , collect distillate (Distillation)
Aldehyde
Carboxylic acid
-1 + 1
ON carbon increase
Alcohol
H OH
‫׀‬ ‫׀‬
CH3- C= O + [O] CH3- C =O
H H
‫׀‬ ‫׀‬
CH3- C -O-H + [O] CH3- C = O
‫׀‬
H
+ 1 + 3
ON carbon increaseAldehyde
Primary 10
– Oxidised to Aldehyde and Carboxylic acid
Alcohol to Carboxylic acid (Reflux)
1. Acidified dichromate(VI)/permanganate(VII)
2.Warm it , collect distillate (Distillation)
Alcohol oxidize to Aldehyde
• MnO4
-
reduce from purple (Mn7+
) to pink (Mn2+
)
• Cr2O7
2-
reducefrom orange (Cr6+
) to green (Cr3+
)
OH O
‫׀‬ ‖
CH3- C – CH3 + [O] CH3- C – CH3 + H2O
0 + 2
ON carbon increase
Alcohol Ketone
Alcohol to Ketone (Reflux)
1. Acidified dichromate(VI)/permanganate(VII)
2.Warm it , collect distillate (Distillation)
Click here oxidation alcohol
RCH2OH + [O] → RCHO + H2O
RCH2OH + 2[O] → RCOOH + H2O
RCH(OH)R + [O] → RCOR + H2O
Oxidationeqn(additionof O)
AldehydeAlcohol
Alcohol
Alcohol
Carboxylic acid
Ketone
Alcohol oxidize to Carboxylic acid
• MnO4
-
reduce from purple (Mn7+
) to pink (Mn2+
)
• Cr2O7
2-
reducefrom orange (Cr6+
) to green (Cr3+
)
distillation
reflux
Aldehyde turn to carboxylic acid
Aldehyde
Alcohol
reflux
Alcohol turn to ketone
Class Functional Suffix Formula
Ester Ester - oate R –COO-R
Number
carbon
IUPAC name Structure formula Molecular
formula
1 Methyl methanoate HCOOCH3
R–COO-R
2 Methyl ethanoate CH3COOCH3
R–COO-R
3 Methyl propanoate CH3CH2COOCH3
R–COO-R
4 Methyl butanoate CH3CH2CH2COOCH3 R–COO-R
methyl methanoate methyl ethanoate methyl propanoate
O H
‖ ‫׀‬
H - C – O – C - H
‫׀‬
H
H O H
‫׀‬ ‖ ‫׀‬
H - C - C – O - C - H
‫׀‬ ‫׀‬
H H
H H O H
‫׀‬ ‫׀‬ ‖ ‫׀‬
H - C – C – C – O - C - H
‫׀‬ ‫׀‬ ‫׀‬
H H H
Hydrocarbon skeleton Functional gp
Esterification
O
‖
H - C – O-H
H
‫׀‬
H- O – C – H
‫׀‬
H
O H
‖ ‫׀‬
H - C – O – C – H + H2O
‫׀‬
H
Ester
Condensation rxn
↔+
Methanoic acid Methanol Methyl methanoate
Esterification (reversible rxn)
After reflux – reach equilibrium
Acid and alcohol (reflux)
Conc H2SO4 (catalyst) used
Water produced
condensation
reflux
Ester purified and distill
Click here ester preparation
H O H
‫׀‬ ‖ ‫׀‬
H - C - C – O - C – H + H2O
‫׀‬ ‫׀‬
H H
H
‫׀‬
H- O – C – H
‫׀‬
H
H O
‫׀‬ ‖
H - C - C – OH
‫׀‬
H
CH3COOH + CH3OH → CH3COOCH3 + H2O
H O H H
‫׀‬ ‖ ‫׀‬ ‫׀‬
H – C – C– O - C–C-H
‫׀‬ ‫׀‬ ‫׀‬
H H H
+
Ethanoic acid Methanol Methyl ethanoate
↔
H H
‫׀‬ ‫׀‬
H- O- C– C – H
‫׀‬ ‫׀‬
H H
H O
‫׀‬ ‖
H – C – C - OH
‫׀‬
H
condensation
CH3COOH + CH3CH2OH → CH3COOCH2CH3 + H2O
+
condensation
↔
Ethanoic acid Ethanol Ethyl ethanoate
+ H2O
H
‫׀‬
CH3 – C – CI
‫׀‬
H
H
‫׀‬
H - C – CI
‫׀‬
H
H H
‫׀‬ ‫׀‬
H - C – C – CI
‫׀‬ ‫׀‬
H H
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – CI
‫׀‬ ‫׀‬ ‫׀‬
H H H
Hydrocarbon skeleton Functional gp
Primary 1 0
1 alkyl /R gp bond to C attach to CI
Secondary 2 0
2 alkyl/R gp bond to C attach to CI
H
‫׀‬
CH3 – C – CI
‫׀‬
CH3
H H H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H CI H
Tertiary 3 0
3 alkyl/R gp bond to C attach to CI
CH3
‫׀‬
CH3 – C – CI
‫׀‬
CH3
R
‫׀‬
R – C – CI
‫׀‬
R
Reactivityfor Halogenoalkane
Class Functional Prefix Example
Halogenoalkane F, CI, Br, I - chloro chloroethane
Number
carbon
IUPAC name Structure formula Molecular
formula
1 chloromethane CH3CI CH3CI
2 chloroethane CH3CH2CI C2H5CI
3 chloropropane CH3CH2CH2CI C3H7CI
4 chlorobutane CH3(CH2)2CH2CI C4H9CI
chloromethane chloroethane chloropropane
Reactivityfor halogenoalkane
• Carbon bond to halogen – F, CI, Br, I
• High electronegativityon halogengp
• High reactivity– due to polarity of C+
- Br -
Nucleophile
– species with lone pair electron
– donate electron pair (Lewis base)
Chemical rxn Halogenoalkane
C - Br
ᵟ+ ᵟ-
electron
Electron deficient
carbon
O–H
..
..
ᵟ- ᵟ+
C
ᵟ+
Substitution rxn
CH3CH2CI + OH-
→ CH3CH2OH + CI-
H H
‫׀‬ ‫׀‬
H - C – C – CI
‫׀‬ ‫׀‬
H H
+ OH-
ᵟ+ ᵟ-
H H
‫׀‬ ‫׀‬
H - C – C – OH + CI-
‫׀‬ ‫׀‬
H H
H Br H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
CH3CHBrCH3 + OH-
→ CH3CHOHCH3 + Br-
+ OH-
H OH H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H + Br-
‫׀‬ ‫׀‬ ‫׀‬
H H H
ᵟ+
ᵟ-
CH3 H
‫׀‬ ‫׀‬
CH3 – C – C – CI
‫׀‬ ‫׀‬
CH3 H
C - Br
Reactivityfor halogenoalkane
• Carbon bondto halogen – F, CI, Br, I
• High electronegativityon halogen gp
• High reactivity – due to polarity of C+
- CI -
C - Br
ᵟ+ ᵟ-
electron
Electron deficient carbon
OH
..ᵟ-ᵟ+
Nucleophilic Substitutionrxn
CH3CH2CI + OH-
→ CH3CH2OH + CI-
H H
‫׀‬ ‫׀‬
H - C – C – CI
‫׀‬ ‫׀‬
H H
+ OH-
ᵟ+ ᵟ-
H H
‫׀‬ ‫׀‬
H - C – C – OH + CI-
‫׀‬ ‫׀‬
H H
H Br H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
CH3CHBrCH3 + OH-
→ CH3CHOHCH3 + Br-
+ OH-
H OH H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H + Br-
‫׀‬ ‫׀‬ ‫׀‬
H H H
ᵟ+ ᵟ-
Nucleophile and Substitution
Electrophile
- Electron deficient
- Accept lone pair
- Positive charge
- Lewis Acid
ElectrophileandAddition
vs
Reactivityof Alkene
- High reactivity - Unstable bondbet C = C
- High reactivity – Weak pi bond overlapbet p orbital
- Unsaturated hydrocarbon – ᴨ bondoverlap
C = C
Electron rich π electron
ᵟ- ᵟ-
H
ᵟ+
C = C
ᵟ-ᵟ-
E
ᵟ+
E+ Electron deficient
Nu
ᵟ-
ᵟ-
Nucleophile
– Lone pair electron
– Donate electron pair
- Lewis Base
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
CH2=CH2 + Br2 → CH2BrCH2Br
+ Br – Br
ᵟ- ᵟ+
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
Br Br
vs
CH2=CH2 + HCI → CH3CH2CI
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
ᵟ-
+ H – CIᵟ+
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H CI
ElectrophilicAddition rxn
Electrophile
- Electron deficient
- Accept lone pair
- Positive charge
- Lewis Acid
ᵟ-
Electron rich region
ElectrophilicSubstitutionrxn
C6H6 + Br2 C6H5Br + HBr
+ Br-Br
ᵟ+
+ NO2
+
ᵟ+
Electrophileand SubstitutionElectrophileandAddition
vs
C = C
Electron rich π electron
ᵟ- ᵟ-
H
ᵟ+
C = C
ᵟ-ᵟ-
E
ᵟ+
E+ Electron deficient
E
ᵟ+
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
CH2=CH2 + Br2 → CH2BrCH2Br
+ Br – Br
ᵟ- ᵟ+
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
Br Br
vs
CH2=CH2 + HCI → CH3CH2CI
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
ᵟ- + H – CIᵟ+
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H CI
ElectrophilicAddition rxn
E
Electrophile
- Electron deficient
- Accept lone pair
- Positive charge
- Lewis Acid
ᵟ++
H E
+ H
Electron rich region
H
Br
+ HBr
C6H6 + HNO3 C6H5NO2 + HCI
AICI3 dry ether
warm/Conc H2SO4
H NO2
Reactivityof Alkene
- High reactivity - Unstable bondbet C = C
- High reactivity – Weak pi bond overlapbet p orbital
- Unsaturated hydrocarbon – ᴨ bondoverlap
Reactivityof Benzene (Unreactive)
- Delocalization ofelectron in ring
- Stabilitydue to delocalized π electron
- Substitution instead of Addition
C6H6 – no reaction
with brown Br2(I)
ethene decolourize
brown Br2(I)
benzene –stable (unreactive) toward addition rxn
C - Br OH
..ᵟ-ᵟ+
Nucleophile
Electrophile
- Electron deficient
- Accept lone pair
- Positive charge
- Lewis Acid
Electrophile
H
ᵟ+
C = C
ᵟ-
Nucleophile
– Lone pair electron
– Donate electron pair
- Lewis Base
Organic Rxn
Addition rxn
Substitution rxn
Nucleophilic Substitution
Free RadicalSubstitution
ElectrophilicSubstitutionElectrophilicAddition rxn
Free radicle
CI CI
CI CI. .
:
Radical (unpair electron)
uv radiation
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
+ Br – Br
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
Br Br
ᵟ+
ᵟ-
H H
‫׀‬ ‫׀‬
H - C – C – CI
‫׀‬ ‫׀‬
H H
+ OH-
H H
‫׀‬ ‫׀‬
H - C – C – OH + CI-
‫׀‬ ‫׀‬
H H
ᵟ-ᵟ+
H
E+ + H
Eᵟ+
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
CI CI
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H CI
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H OH
Add HCI
CI2 / UV
H H
‫׀‬ ‫׀‬
H - C – C – CI
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – OH + CI-
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – NH2 + CI-
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – CN + CI-
‫׀‬ ‫׀‬
H H
NH3
OH-
CN-
H
‫׀‬
H - C – H
‫׀‬
H
H
‫׀‬
H - C – CI + H
‫׀‬
H
CI2 → 2 CI•
CH3• + CI2 → CH3CI + CI•
CI• + CH4 → HCI + CH3•
C - Br OH
..ᵟ-ᵟ+
Nucleophile
Electrophile
- Electron deficient
- Accept lone pair
- Positive charge
- Lewis Acid
Electrophile
H
ᵟ+
C = C
ᵟ-
Nucleophile
– lone pair electron
– donate electron pair
- Lewis Base
Free radicle
CI CI
CI CI. .
:
Radical (unpair electron)
uv radiation
H H
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
CI CI
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H CI
H H
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H OH
Add HCI
CI2 / UV
H H
‫׀‬ ‫׀‬
H - C – C – CI
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – OH + CI-
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – NH2 + CI-
‫׀‬ ‫׀‬
H H
H H
‫׀‬ ‫׀‬
H - C – C – CN + CI-
‫׀‬ ‫׀‬
H H
NH3
OH-
CN-
H
‫׀‬
H - C – H
‫׀‬
H
H
‫׀‬
H - C – CI + H
‫׀‬
H
CI2 → 2 CI•
CH3• + CI2 → CH3CI + CI•
CI• + CH4 → HCI + CH3•
Alkene – Addition rxn Halogenoalkane – Substitution rxn Alkane - Radical substitution
H OH
‫׀‬ ‫׀‬
H - C – C – H
‫׀‬ ‫׀‬
H H
H O
‫׀‬ ‖
H - C – C – H
‫׀‬
H
H O
‫׀‬ ‖
H - C – C – OH
‫׀‬
H
H O H
‫׀‬ ‖ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬
H H
H OH H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H H H
H OH H
‫׀‬ ‫׀‬ ‫׀‬
H - C – C – C – H
‫׀‬ ‫׀‬ ‫׀‬
H CH3 H
Alcohol – Oxidation rxn
10 alcohol 20 alcohol 30 alcohol
carboxylic acid aldehyde ketone
no reaction
‫׀‬ ‫׀‬
C - C –OH
‫׀‬ ‫׀‬
O
‖
C – C – C
O
‖
C – C – H
O
‖
C – C – OH
O
‖
C –C – C – O – C – C
O H
‖ ‫׀‬
C – C – N – C – C
No
reaction
1o
alcohol
[O]/Cr2O7/H+
Aldehyde
Ketone Carboxylic Acid
Free radical substitution
CI2/ UV
Halogenoalkane
Alkane
3o
alcohol
[O]/ Cr2O7/H+
Substitution
warm / OH-
Alcohol
Substitution / CN-
Amine
Nitrile
Alcohol
Condensation
Amide
Amine
Carboxylic Acid
Alkene
Elimination
100C /Conc alcoholic OH-
Alkane Halogenoalkane Dihalogenoalkane
Condensation
Ester
Addition
Polymerisation
X
‫׀‬ ‫׀‬
C – C – CI
‫׀‬ ‫׀‬
‫׀‬ ‫׀‬
C = C
‫׀‬ ‫׀‬
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C – C – C – C
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
‫׀‬ ‫׀‬
C – C
‫׀‬ ‫׀‬
H CI
‫׀‬ ‫׀‬
C – C
‫׀‬ ‫׀‬
CI CI
‫׀‬ ‫׀‬
C – C
‫׀‬ ‫׀‬
Br Br
‫׀‬ ‫׀‬
C – C
‫׀‬ ‫׀‬
‫׀‬ ‫׀‬
C – C – OH
‫׀‬ ‫׀‬
‫׀‬ ‫׀‬
C – C – CN
‫׀‬ ‫׀‬
‫׀‬ ‫׀‬
C – C – NH2
‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬
C – C – C –NH2
‫׀‬ ‫׀‬ ‫׀‬
‫׀‬ ‫׀‬
C – C – COOH
‫׀‬ ‫׀‬
Start here
PolyAlkene
‫׀‬ ‫׀‬
C – C
‫׀‬ ‫׀‬
H H

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IB Chemistry on Free radical substitution, Addition and Nucleophilic substitution

  • 1. Class Functionalgp Suffix Example Formula Alkane C - C - ane ethane CnH2n+2 H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H H H ‫׀‬ H - C – H ‫׀‬ H H H H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ H H H H H H H ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ H H H H Number carbon Word IUPAC name Structure formula Molecular formula 1 Meth Methane CH4 CH4 2 Eth Ethane CH3CH3 C2H6 3 Prop Propane CH3CH2CH3 C3H8 4 But Butane CH3(CH2)2CH3 C4H10 5 Pent Pentane CH3(CH2)3CH3 C5H12 6 Hex Hexane CH3(CH2)4CH3 C6H14 7 Hept Heptane CH3(CH2)5CH3 C7H16 8 Oct Octane CH3(CH2)6CH3 C8H18 9 Non Nonane CH3(CH2)7CH3 C9H20 10 Dec Decane CH3(CH2)8CH3 C10H22 methane ethane propane butane Saturated hydrocarbon (C – C single bond) Chemical rxn AlkaneReactivityfor Alkanes Combustion rxn Complete combustion – produce CO2 + H2O • C2H6 + 7/2O2 → 2CO2 + 3H2O Incomplete combustion – produce C, CO, CO2, H2O • 2C3H8 + 7O2 → 2C + 2CO + 8H2O + 2CO2 Free Radical Substitution rxn Free Radical Substitution Mechanism - Homolytic fission- bond break by radical form. - Covalent bond split, each atom obtain one electron (unpair e) - UV needed - Radical react with molecule - Radical + radical → molecule CH4 + CI2 → CH3CI + HCI • Low reactivity - Strongstable bondbet C - C, C - H • Low reactivity - Low polarity of C - H bond • Saturatedhydrocarbon – Non polarbond Initiation Propagation Radical (dot) Termination homolytic fission Radical recycle again 1 2
  • 2. H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H H H H ‫׀‬ ‫׀‬ ‫׀‬ C = C – C - H ‫׀‬ ‫׀‬ H H H H H H ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C = C – C – C - H ‫׀‬ ‫׀‬ ‫׀‬ H H H Unsaturated hydrocarbon (C = C double bond) H H H H H ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C = C – C – C – C - H ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ H H H H ethene propene butene pentene Reactivityfor Alkene - High reactivity - Unstable bondbet C = C - High reactivity – Weak pi bond overlapbet p orbital - Unsaturated hydrocarbon – ᴨ bondoverlap Combustion rxn Chemicalrxn Alkane Complete combustion – produce CO2 + H2O C2H4 + 3O2 → 2CO2 + 2H2O Incomplete combustion – produce C, CO, CO2, H2O 2C2H4 + 7/2O2 → 2C + CO + 4H2O + CO2 CH2 = CH2 + Br2 → CH2BrCH2Br CH2 = CH2 + HCI → CH3CH2CI CH2 = CH2 + H2O → CH3CH2OH Addition rxn H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ CI CI H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ Br Br H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H CI H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H OH 1 2 Polymerization(Additionrxn)3 Polymers are long chains molecules (plastics) • Join repeat units call monomers • Addition and condensation polymerization • Monomers double bond (unsaturated) • Repeat units join together by covalent bond without loss of any molecule ethene polyethene add monomer polymer propene polypropylene add monomer H CH3 H CH3 monomer monomer chloroethene polychloroethene (PVC) tetrafluoroethene polytetrafluoroethene (PTFE) H CI H CI F F F F F F F F polymerization polymer Alkene decolourize brown liq Br2 Class Functional Suffix Example Formula Alkene Alkenyl - ene ethene CnH2n
  • 3. OH ‫׀‬ CH3-C– CH3 + [O] No product ‫׀‬ CH3 OH O ‫׀‬ ‖ CH3- C–CH3 + [O] CH3- C – CH3 + H2O H ‫׀‬ CH3 – C – OH ‫׀‬ H Class Functional Suffix Example Formula Alcohol Hydroxyl - ol methanol CnH2n+1OH Number carbon IUPAC name Structure formula Molecular formula 1 Methanol CH3OH CH3OH 2 Ethanol CH3CH2OH C2H5OH 3 Propanol CH3CH2CH2OH C3H7OH 4 Butanol CH3(CH2)2CH2OH C4H9OH methanol ethanol propanol butanol H ‫׀‬ H - C – OH ‫׀‬ H H H ‫׀‬ ‫׀‬ H - C – C – OH ‫׀‬ ‫׀‬ H H H H H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – OH ‫׀‬ ‫׀‬ ‫׀‬ H H H H H H H ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – C – OH ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ H H H H Hydrocarbon skeleton Functional gp Chemical rxn AlcoholReactivityfor Alcohol Primary 1 0 1 alkyl /R gp bond to C attach to OH CH3 H ‫׀‬ ‫׀‬ CH3 – C – C – OH ‫׀‬ ‫׀‬ CH3 H Combustionrxn Complete combustion–produceCO2 + H2O C2H6OH + 3O2 → 2CO2 + 3H2O Incomplete combustion-produceC, CO, CO2, + H2O 2C2H5OH + 4O2 → C + 2CO + 6H2O + CO2 Oxidation rxn Secondary 2 0 2 alkyl/R gp bond to C attach to OH H ‫׀‬ CH3 – C – OH ‫׀‬ CH3 H H H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ H OH H Tertiary 3 0 3 alkyl/R gp bond to C attach to OH CH3 ‫׀‬ CH3 – C – OH ‫׀‬ CH3 R ‫׀‬ R – C – OH ‫׀‬ R H ‫׀‬ CH3-CH2-OH + [O] CH3- C = O + H2O MnO4 - /H+ K2Cr2O7/H+ Primary 10 – Oxidised to Aldehyde and Carboxylic acid H OH ‫׀‬ ‫׀‬ CH3- C= O + [O] CH3-C=O Secondary 20 - Oxidised to Ketone Tertiary 30 - Cannot be Oxidised MnO4 - /H+ K2Cr2O7/H+ MnO4 - /H+ K2Cr2O7/H+ MnO4 - /H+ K2Cr2O7/H+ 1 1 Esterificationrxn3 O H ‖ ‫׀‬ H - C – O – C – H + H2O ‫׀‬ H H ‫׀‬ H- O – C – H ‫׀‬ H O ‖ H - C – O-H +
  • 4. Chemical rxn Alcohol Oxidation rxn – oxidized carbon attach to OH Primary 10 – Oxidised to Aldehyde and Carboxylic acid Secondary 20 - Oxidised to Ketone Tertiary 30 - Cannot be Oxidised OH ‫׀‬ CH3-C– CH3 + [O] No product ‫׀‬ CH3 MnO4 - /H+ K2Cr2O7/H+ MnO4 - /H+ K2Cr2O7/H+ MnO4 - /H+ K2Cr2O7/H+ Alcohol to Aldehyde (Distillation) 1. Acidified dichromate(VI)/permanganate(VII) 2.Warm it , collect distillate (Distillation) Aldehyde Carboxylic acid -1 + 1 ON carbon increase Alcohol H OH ‫׀‬ ‫׀‬ CH3- C= O + [O] CH3- C =O H H ‫׀‬ ‫׀‬ CH3- C -O-H + [O] CH3- C = O ‫׀‬ H + 1 + 3 ON carbon increaseAldehyde Primary 10 – Oxidised to Aldehyde and Carboxylic acid Alcohol to Carboxylic acid (Reflux) 1. Acidified dichromate(VI)/permanganate(VII) 2.Warm it , collect distillate (Distillation) Alcohol oxidize to Aldehyde • MnO4 - reduce from purple (Mn7+ ) to pink (Mn2+ ) • Cr2O7 2- reducefrom orange (Cr6+ ) to green (Cr3+ ) OH O ‫׀‬ ‖ CH3- C – CH3 + [O] CH3- C – CH3 + H2O 0 + 2 ON carbon increase Alcohol Ketone Alcohol to Ketone (Reflux) 1. Acidified dichromate(VI)/permanganate(VII) 2.Warm it , collect distillate (Distillation) Click here oxidation alcohol RCH2OH + [O] → RCHO + H2O RCH2OH + 2[O] → RCOOH + H2O RCH(OH)R + [O] → RCOR + H2O Oxidationeqn(additionof O) AldehydeAlcohol Alcohol Alcohol Carboxylic acid Ketone Alcohol oxidize to Carboxylic acid • MnO4 - reduce from purple (Mn7+ ) to pink (Mn2+ ) • Cr2O7 2- reducefrom orange (Cr6+ ) to green (Cr3+ ) distillation reflux Aldehyde turn to carboxylic acid Aldehyde Alcohol reflux Alcohol turn to ketone
  • 5. Class Functional Suffix Formula Ester Ester - oate R –COO-R Number carbon IUPAC name Structure formula Molecular formula 1 Methyl methanoate HCOOCH3 R–COO-R 2 Methyl ethanoate CH3COOCH3 R–COO-R 3 Methyl propanoate CH3CH2COOCH3 R–COO-R 4 Methyl butanoate CH3CH2CH2COOCH3 R–COO-R methyl methanoate methyl ethanoate methyl propanoate O H ‖ ‫׀‬ H - C – O – C - H ‫׀‬ H H O H ‫׀‬ ‖ ‫׀‬ H - C - C – O - C - H ‫׀‬ ‫׀‬ H H H H O H ‫׀‬ ‫׀‬ ‖ ‫׀‬ H - C – C – C – O - C - H ‫׀‬ ‫׀‬ ‫׀‬ H H H Hydrocarbon skeleton Functional gp Esterification O ‖ H - C – O-H H ‫׀‬ H- O – C – H ‫׀‬ H O H ‖ ‫׀‬ H - C – O – C – H + H2O ‫׀‬ H Ester Condensation rxn ↔+ Methanoic acid Methanol Methyl methanoate Esterification (reversible rxn) After reflux – reach equilibrium Acid and alcohol (reflux) Conc H2SO4 (catalyst) used Water produced condensation reflux Ester purified and distill Click here ester preparation H O H ‫׀‬ ‖ ‫׀‬ H - C - C – O - C – H + H2O ‫׀‬ ‫׀‬ H H H ‫׀‬ H- O – C – H ‫׀‬ H H O ‫׀‬ ‖ H - C - C – OH ‫׀‬ H CH3COOH + CH3OH → CH3COOCH3 + H2O H O H H ‫׀‬ ‖ ‫׀‬ ‫׀‬ H – C – C– O - C–C-H ‫׀‬ ‫׀‬ ‫׀‬ H H H + Ethanoic acid Methanol Methyl ethanoate ↔ H H ‫׀‬ ‫׀‬ H- O- C– C – H ‫׀‬ ‫׀‬ H H H O ‫׀‬ ‖ H – C – C - OH ‫׀‬ H condensation CH3COOH + CH3CH2OH → CH3COOCH2CH3 + H2O + condensation ↔ Ethanoic acid Ethanol Ethyl ethanoate + H2O
  • 6. H ‫׀‬ CH3 – C – CI ‫׀‬ H H ‫׀‬ H - C – CI ‫׀‬ H H H ‫׀‬ ‫׀‬ H - C – C – CI ‫׀‬ ‫׀‬ H H H H H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – CI ‫׀‬ ‫׀‬ ‫׀‬ H H H Hydrocarbon skeleton Functional gp Primary 1 0 1 alkyl /R gp bond to C attach to CI Secondary 2 0 2 alkyl/R gp bond to C attach to CI H ‫׀‬ CH3 – C – CI ‫׀‬ CH3 H H H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ H CI H Tertiary 3 0 3 alkyl/R gp bond to C attach to CI CH3 ‫׀‬ CH3 – C – CI ‫׀‬ CH3 R ‫׀‬ R – C – CI ‫׀‬ R Reactivityfor Halogenoalkane Class Functional Prefix Example Halogenoalkane F, CI, Br, I - chloro chloroethane Number carbon IUPAC name Structure formula Molecular formula 1 chloromethane CH3CI CH3CI 2 chloroethane CH3CH2CI C2H5CI 3 chloropropane CH3CH2CH2CI C3H7CI 4 chlorobutane CH3(CH2)2CH2CI C4H9CI chloromethane chloroethane chloropropane Reactivityfor halogenoalkane • Carbon bond to halogen – F, CI, Br, I • High electronegativityon halogengp • High reactivity– due to polarity of C+ - Br - Nucleophile – species with lone pair electron – donate electron pair (Lewis base) Chemical rxn Halogenoalkane C - Br ᵟ+ ᵟ- electron Electron deficient carbon O–H .. .. ᵟ- ᵟ+ C ᵟ+ Substitution rxn CH3CH2CI + OH- → CH3CH2OH + CI- H H ‫׀‬ ‫׀‬ H - C – C – CI ‫׀‬ ‫׀‬ H H + OH- ᵟ+ ᵟ- H H ‫׀‬ ‫׀‬ H - C – C – OH + CI- ‫׀‬ ‫׀‬ H H H Br H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ H H H CH3CHBrCH3 + OH- → CH3CHOHCH3 + Br- + OH- H OH H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H + Br- ‫׀‬ ‫׀‬ ‫׀‬ H H H ᵟ+ ᵟ- CH3 H ‫׀‬ ‫׀‬ CH3 – C – C – CI ‫׀‬ ‫׀‬ CH3 H
  • 7. C - Br Reactivityfor halogenoalkane • Carbon bondto halogen – F, CI, Br, I • High electronegativityon halogen gp • High reactivity – due to polarity of C+ - CI - C - Br ᵟ+ ᵟ- electron Electron deficient carbon OH ..ᵟ-ᵟ+ Nucleophilic Substitutionrxn CH3CH2CI + OH- → CH3CH2OH + CI- H H ‫׀‬ ‫׀‬ H - C – C – CI ‫׀‬ ‫׀‬ H H + OH- ᵟ+ ᵟ- H H ‫׀‬ ‫׀‬ H - C – C – OH + CI- ‫׀‬ ‫׀‬ H H H Br H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ H H H CH3CHBrCH3 + OH- → CH3CHOHCH3 + Br- + OH- H OH H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H + Br- ‫׀‬ ‫׀‬ ‫׀‬ H H H ᵟ+ ᵟ- Nucleophile and Substitution Electrophile - Electron deficient - Accept lone pair - Positive charge - Lewis Acid ElectrophileandAddition vs Reactivityof Alkene - High reactivity - Unstable bondbet C = C - High reactivity – Weak pi bond overlapbet p orbital - Unsaturated hydrocarbon – ᴨ bondoverlap C = C Electron rich π electron ᵟ- ᵟ- H ᵟ+ C = C ᵟ-ᵟ- E ᵟ+ E+ Electron deficient Nu ᵟ- ᵟ- Nucleophile – Lone pair electron – Donate electron pair - Lewis Base H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H CH2=CH2 + Br2 → CH2BrCH2Br + Br – Br ᵟ- ᵟ+ H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ Br Br vs CH2=CH2 + HCI → CH3CH2CI H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H ᵟ- + H – CIᵟ+ H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H CI ElectrophilicAddition rxn
  • 8. Electrophile - Electron deficient - Accept lone pair - Positive charge - Lewis Acid ᵟ- Electron rich region ElectrophilicSubstitutionrxn C6H6 + Br2 C6H5Br + HBr + Br-Br ᵟ+ + NO2 + ᵟ+ Electrophileand SubstitutionElectrophileandAddition vs C = C Electron rich π electron ᵟ- ᵟ- H ᵟ+ C = C ᵟ-ᵟ- E ᵟ+ E+ Electron deficient E ᵟ+ H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H CH2=CH2 + Br2 → CH2BrCH2Br + Br – Br ᵟ- ᵟ+ H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ Br Br vs CH2=CH2 + HCI → CH3CH2CI H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H ᵟ- + H – CIᵟ+ H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H CI ElectrophilicAddition rxn E Electrophile - Electron deficient - Accept lone pair - Positive charge - Lewis Acid ᵟ++ H E + H Electron rich region H Br + HBr C6H6 + HNO3 C6H5NO2 + HCI AICI3 dry ether warm/Conc H2SO4 H NO2 Reactivityof Alkene - High reactivity - Unstable bondbet C = C - High reactivity – Weak pi bond overlapbet p orbital - Unsaturated hydrocarbon – ᴨ bondoverlap Reactivityof Benzene (Unreactive) - Delocalization ofelectron in ring - Stabilitydue to delocalized π electron - Substitution instead of Addition C6H6 – no reaction with brown Br2(I) ethene decolourize brown Br2(I) benzene –stable (unreactive) toward addition rxn
  • 9. C - Br OH ..ᵟ-ᵟ+ Nucleophile Electrophile - Electron deficient - Accept lone pair - Positive charge - Lewis Acid Electrophile H ᵟ+ C = C ᵟ- Nucleophile – Lone pair electron – Donate electron pair - Lewis Base Organic Rxn Addition rxn Substitution rxn Nucleophilic Substitution Free RadicalSubstitution ElectrophilicSubstitutionElectrophilicAddition rxn Free radicle CI CI CI CI. . : Radical (unpair electron) uv radiation H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H + Br – Br H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ Br Br ᵟ+ ᵟ- H H ‫׀‬ ‫׀‬ H - C – C – CI ‫׀‬ ‫׀‬ H H + OH- H H ‫׀‬ ‫׀‬ H - C – C – OH + CI- ‫׀‬ ‫׀‬ H H ᵟ-ᵟ+ H E+ + H Eᵟ+ H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ CI CI H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H CI H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H OH Add HCI CI2 / UV H H ‫׀‬ ‫׀‬ H - C – C – CI ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – OH + CI- ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – NH2 + CI- ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – CN + CI- ‫׀‬ ‫׀‬ H H NH3 OH- CN- H ‫׀‬ H - C – H ‫׀‬ H H ‫׀‬ H - C – CI + H ‫׀‬ H CI2 → 2 CI• CH3• + CI2 → CH3CI + CI• CI• + CH4 → HCI + CH3•
  • 10. C - Br OH ..ᵟ-ᵟ+ Nucleophile Electrophile - Electron deficient - Accept lone pair - Positive charge - Lewis Acid Electrophile H ᵟ+ C = C ᵟ- Nucleophile – lone pair electron – donate electron pair - Lewis Base Free radicle CI CI CI CI. . : Radical (unpair electron) uv radiation H H ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ CI CI H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H CI H H ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H OH Add HCI CI2 / UV H H ‫׀‬ ‫׀‬ H - C – C – CI ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – OH + CI- ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – NH2 + CI- ‫׀‬ ‫׀‬ H H H H ‫׀‬ ‫׀‬ H - C – C – CN + CI- ‫׀‬ ‫׀‬ H H NH3 OH- CN- H ‫׀‬ H - C – H ‫׀‬ H H ‫׀‬ H - C – CI + H ‫׀‬ H CI2 → 2 CI• CH3• + CI2 → CH3CI + CI• CI• + CH4 → HCI + CH3• Alkene – Addition rxn Halogenoalkane – Substitution rxn Alkane - Radical substitution H OH ‫׀‬ ‫׀‬ H - C – C – H ‫׀‬ ‫׀‬ H H H O ‫׀‬ ‖ H - C – C – H ‫׀‬ H H O ‫׀‬ ‖ H - C – C – OH ‫׀‬ H H O H ‫׀‬ ‖ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ H H H OH H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ H H H H OH H ‫׀‬ ‫׀‬ ‫׀‬ H - C – C – C – H ‫׀‬ ‫׀‬ ‫׀‬ H CH3 H Alcohol – Oxidation rxn 10 alcohol 20 alcohol 30 alcohol carboxylic acid aldehyde ketone no reaction
  • 11. ‫׀‬ ‫׀‬ C - C –OH ‫׀‬ ‫׀‬ O ‖ C – C – C O ‖ C – C – H O ‖ C – C – OH O ‖ C –C – C – O – C – C O H ‖ ‫׀‬ C – C – N – C – C No reaction 1o alcohol [O]/Cr2O7/H+ Aldehyde Ketone Carboxylic Acid Free radical substitution CI2/ UV Halogenoalkane Alkane 3o alcohol [O]/ Cr2O7/H+ Substitution warm / OH- Alcohol Substitution / CN- Amine Nitrile Alcohol Condensation Amide Amine Carboxylic Acid Alkene Elimination 100C /Conc alcoholic OH- Alkane Halogenoalkane Dihalogenoalkane Condensation Ester Addition Polymerisation X ‫׀‬ ‫׀‬ C – C – CI ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C = C ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C – C – C – C ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C – C ‫׀‬ ‫׀‬ H CI ‫׀‬ ‫׀‬ C – C ‫׀‬ ‫׀‬ CI CI ‫׀‬ ‫׀‬ C – C ‫׀‬ ‫׀‬ Br Br ‫׀‬ ‫׀‬ C – C ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C – C – OH ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C – C – CN ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C – C – NH2 ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C – C – C –NH2 ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ ‫׀‬ C – C – COOH ‫׀‬ ‫׀‬ Start here PolyAlkene ‫׀‬ ‫׀‬ C – C ‫׀‬ ‫׀‬ H H