1. IB Chemistry Power Points
Topics 10 & 20
Organic Chemistry
www.pedagogics.ca
Reaction Summary

2. Reactions and
Mechanisms
SL and HL

3. Conc OH-, ethanol, Δ (elimination)
1o or 2o R-X
3o R-X
Homolytic fission, UV light (substitution) KCN
SN1 H2, Ni catalyst,
NaOH, Δ (substitution)
Δ, pressure
H2, Ni catalyst, Δ (addition)
3o R-X
(reduction)
SN2
1o R-X
(addition)
X2 or HX, Δ
(condensation)
with R-COOH
(addition)
H2O, [H2SO4], Δ
polymerization
addition
(oxidation)
H+,Cr2O72-, Δ
reflux
(condensation)
with R-OH

4. SL Core
Pathways

5. Combustion reactions not
included in this summary. You
are still responsible for the
stoichiometry of these reactions,
problems using PV=nRT, and
empirical formula – combustion
analysis problems
Only two mechanisms are
required at SL
- Homolytic fission
- Nucleophilic substitution

6. Homolytic fission, UV light
Alkane Reactions
Making halogenoalkanes by
process of homolytic fission.
Know what a radical is
Understand and memorize the
the 3 steps – Initiation,
Propagation and Termination
This reaction REQUIRES light

7. Homolytic fission, UV light
Alkene Addition Reactions
With hydrogen gas to make
H2, Ni catalyst, Δ (addition)
alkanes

8. Homolytic fission, UV light
Alkene Addition Reactions
With hydrogen gas to make
H2, Ni catalyst, Δ (addition)
alkanes
With halogens or HX’s to make
halogenoalkanes (R-X)
(addition)
X2 or HX, Δ

9. Homolytic fission, UV light
Alkene Addition Reactions
With hydrogen gas to make
H2, Ni catalyst, Δ (addition)
alkanes
With halogens or HX’s to make
halogenoalkanes (R-X)
(addition)
X2 or HX, Δ
With water to make alcohols
(R-OH)
(addition)
H2O, [H2SO4], Δ

10. Homolytic fission, UV light
Alkene Addition Reactions
With hydrogen gas to make
H2, Ni catalyst, Δ (addition)
alkanes
With halogens or HX’s to make
halogenoalkanes (R-X)
(addition)
X2 or HX, Δ
With water to make alcohols
(R-OH)
(addition)
H2O, [H2SO4], Δ
Monomer subunits combine to
polymerization
make polymers
addition

11. Oxidation of Alcohols
Be able to recognize 1o, 2o and 3o
alcohols
Oxidizing agent is usually potassium
dichromate.
As dichromate ions are reduced
color changes from orange to green
Reflux – heated mixture is
2o R-OH are oxidized to (oxidation) condensed and re-reacted
ketones. 3o are resistant H+,Cr2O72-, Δ
reflux
to oxidation
1o R-OH are oxidized first to
aldehydes and then to carboxylic
acids

12. Nucleophilic Substitution
NaOH, Δ (substitution)
Be able to recognize 1o, 2o and 3o
halogenoalkanes

13. Nucleophilic Substitution SN1
NaOH, Δ (substitution)
3o R-X
3o halogenoalkanes react with
OH- to make alcohols by SN1
mechanism. (carbocation
intermediate)

14. Nucleophilic Substitution
NaOH, Δ (substitution)
1o halogenoalkanes react with
OH- to make alcohols by SN2
mechanism. (transition state) SN2
1o R-X

15. Homolytic fission, UV light
SN1
NaOH, Δ (substitution)
H2, Ni catalyst, Δ (addition)
3o R-X
SN2
1o R-X
(addition)
X2 or HX, Δ
(addition)
H2O, [H2SO4], Δ
polymerization
addition
(oxidation)
H+,Cr2O72-, Δ
reflux

16. HL
Pathways

17. Conc OH-, ethanol, Δ (elimination)
1o or 2o R-X
3o R-X
Homolytic fission, UV light (substitution) KCN
SN1 H2, Ni catalyst,
NaOH, Δ (substitution)
Δ, pressure
H2, Ni catalyst, Δ (addition)
3o R-X
(reduction)
SN2
1o R-X
(addition)
X2 or HX, Δ
(condensation)
with R-COOH
(addition)
H2O, [H2SO4], Δ
polymerization
addition
(oxidation)
H+,Cr2O72-, Δ
reflux
(condensation)
with R-OH

18. HL adds nucleophilic substitution
reactions with cyanide ion acting as
the nucleophile and
(substitution) KCN
SN1
3o R-X
SN2
1o R-X

19. HL adds nucleophilic substitution
reactions with cyanide ion acting as the
nucleophile and with ammonia
(substitution) KCN
SN1
3o R-X
SN2
1o R-X

20. Nitriles can be REDUCED to amines in different ways
H2, Ni catalyst,
Δ, pressure
(reduction)

21. Conc OH-, ethanol, Δ (elimination)
Elimination reaction mechanisms
compete with substitution when
halogenoalkanes react with some
nucleophiles
Product is an alkene
Which mechanism is favored depends
on the reaction conditions

22. Conc OH-, ethanol, Δ (elimination)
1o or 2o R-X
3o R-X
Elimination reaction mechanisms
compete with substitution when
halogenoalkanes react with some
nucleophiles
Product is an alkene
Which mechanism is favored depends
on the reaction conditions

23. Condensation reactions include
Esterification – where an ester and
water are formed by the reaction
between a carboxylic acid and an
alcohol
(condensation)
with R-OH

24. Condensation reactions include
– where an amide and water are
formed by the reaction between a
carboxylic acid and an amine
(condensation)
with R-COOH
(condensation)
with R-OH

25. Conc OH-, ethanol, Δ (elimination)
1o or 2o R-X
3o R-X
Homolytic fission, UV light (substitution) KCN
SN1 H2, Ni catalyst,
NaOH, Δ (substitution)
Δ, pressure
H2, Ni catalyst, Δ (addition)
3o R-X
(reduction)
SN2
1o R-X
(addition)
X2 or HX, Δ
(condensation)
with R-COOH
(addition)
H2O, [H2SO4], Δ
polymerization
addition
(oxidation)
H+,Cr2O72-, Δ
reflux
(condensation)
with R-OH