This document describes various classes of organic compounds including alkanes, alkenes, alcohols, esters, and their properties. Alkanes are saturated hydrocarbons with the general formula CnH2n+2. Alkenes are unsaturated hydrocarbons containing carbon-carbon double bonds with the general formula CnH2n. Alcohols contain an -OH functional group and have the general formula CnH2n+1OH. Esters are formed from the condensation reaction between carboxylic acids and alcohols, producing water as a byproduct. Common chemical reactions for each class are also outlined such as combustion, addition, oxidation, and esterification
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1. List and explain the physical properties of aldehydes
2. Differentiate application areas of various Aldehydes
3. Explain methods of various aldehyde preparation methods by using chemical reactions
4. Recognize preparation reactions of Aldehydes
Aldehydes physical properties and preparationKamran Mammadli
1. List and explain the physical properties of aldehydes
2. Differentiate application areas of various Aldehydes
3. Explain methods of various aldehyde preparation methods by using chemical reactions
4. Recognize preparation reactions of Aldehydes
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The third part consists of hydroboration oxidation in alkenes and alkynes by Anti-Markovnikov rule and CSIR questions.
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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