Electrophilic Addition
Nucleophilic Substitution
Electrophilic Substitution
Nucleophilic Addition
Alkylation
Acylation
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Heterolytic
Nitration
Free Radical Addition
Homolytic
Br2
SN1
SN2
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Edexcel organic reaction mechanisms презентация
Содержание
- 1. Edexcel organic reaction mechanisms
- 2. CH4 + Cl2 CH3Cl + HCl Overall
- 3. initiation step two propagation steps termination step
- 4. CH3Cl + Cl2 CH2Cl2 + HCl Overall
- 5. n H2C=CH2 Overall reaction equation polyethene
- 6. initiation step Addition of H2C=CH2 repeats the
- 7. Electrophilic addition CH3CH=CH2 + Br2 CH3CHBrCH2Br bromine
- 8. Electrophilic addition mechanism carbocation 1,2-dibromopropane bromine with propene reaction equation
- 9. Electrophilic addition mechanism carbocation 2-bromobutane hydrogen bromide with trans but-2-ene reaction equation
- 10. hydroxide ion with bromoethane ethanol CH3CH2Br +
- 11. hydroxide ion with bromoethane (SN2) Nucleophilic
- 12. OH- ion with 2-bromo,2-methylpropane (SN1) Nucleophilic
- 13. Nucleophilic substitution propanenitrile CH3CH2I (ethanol) + CN-(aq)
- 14. cyanide ion with iodoethane (SN2) Nucleophilic substitution
- 15. CN- ion with 2-bromo,2-methylpropane (SN1)
- 16. Electrophilic Substitution Nitration of benzene C6H6
- 17. electrophilic substitution mechanism (nitration) 2. Electrophilic attack
- 18. Bromination of benzene C6H6
- 19. Electrophilic substitution mechanism 1. Formation of the
- 20. Alkylation of benzene C6H6
- 21. Alkylation example Three steps in electrophilic substitution
- 22. Alkylation electrophilic substitution mechanism 2 2. Electrophilic
- 23. Acylation of benzene C6H6
- 24. Acylation example Three steps in electrophilic substitution
- 25. Acylation electrophilic substitution mechanism 2 2. Electrophilic
- 26. Nucleophilic Addition RCHO +
- 27. Nucleophilic Addition Mechanism hydrogen cyanide with propanone
- 28. Advice
- 29. Steve Lewis for the Royal Society of Chemistry References
CH4 + Cl2 CH3Cl + HCl Overall reaction equation Conditions ultra violet light excess methane i.e. homolytic breaking of covalent bonds to reduce further substitution Free radical substitution chlorination of methane
Слайд 1Free Radical Substitution
Edexcel organic reaction mechanisms
Click a box below to go
to the mechanism
Слайд 2CH4 + Cl2
CH3Cl + HCl
Overall reaction equation
Conditions
ultra violet light
excess methane
i.e. homolytic
breaking of covalent bonds
to reduce further substitution
Free radical substitution
chlorination of methane
Слайд 3initiation step
two propagation steps
termination step
ultra-violet
minor
termination step
Free radical substitution mechanism
Слайд 4CH3Cl + Cl2
CH2Cl2 + HCl
Overall reaction equations
Conditions
ultra-violet light
CH2Cl2 + Cl2
CHCl3 +
HCl
CHCl3 + Cl2
CCl4 + HCl
excess chlorine
Further free radical substitutions
Слайд 5n H2C=CH2
Overall reaction equation
polyethene
free radical source
i.e. homolytic breaking of covalent
bonds
(a species that generates free radicals
that allow the polymerisation of ethene molecules)
Free radical addition
addition polymerisation of ethene
Conditions
ethene
Слайд 6initiation step
Addition of H2C=CH2 repeats the same way until:
polyethene
Free radical addition
mechanism
chain propagation steps
termination step
Слайд 7Electrophilic addition
CH3CH=CH2
+ Br2
CH3CHBrCH2Br
bromine with propene
hydrogen bromide with but-2-ene
CH3CH=CHCH3
+ HBr
CH3CH2CHBrCH3
2-bromobutane
1,2-dibromopropane
mechanism
mechanism
Слайд 8Electrophilic addition mechanism
carbocation
1,2-dibromopropane
bromine with propene
reaction equation
Слайд 9Electrophilic addition mechanism
carbocation
2-bromobutane
hydrogen bromide with trans but-2-ene
reaction equation
Слайд 10hydroxide ion with bromoethane
ethanol
CH3CH2Br
+ OH-
CH3CH2OH + Br-
(aqueous)
Nucleophilic substitution
mechanism
hydroxide ion with 2-bromo,2-methylpropane
2-methylpropan-2-ol
(CH3)3CBr
+
OH-
(CH3)3COH + Br-
(aqueous)
mechanism
Слайд 11hydroxide ion with bromoethane (SN2)
Nucleophilic substitution mechanism
ethanol
reaction equation
2(species reacting
in
the slowest step)
SN2
S (substitution)
N(nucleophilic)
Слайд 12OH- ion with 2-bromo,2-methylpropane (SN1)
Nucleophilic substitution mechanism
2-methylpropan-2-ol
reaction equation
1(species reacting
in the
slowest step)
SN1
S (substitution)
N(nucleophilic)
Слайд 13Nucleophilic substitution
propanenitrile
CH3CH2I (ethanol)
+ CN-(aq)
CH3CH2CN + I-
cyanide ion with iodoethane
mechanism
cyanide ion with
2-bromo,2-methylpropane
2,2-dimethylpropanenitrile
(CH3)3CBr
(ethanol) + CN-
(CH3)3CCN + Br-
(aqueous)
mechanism
Слайд 14cyanide ion with iodoethane (SN2)
Nucleophilic substitution mechanism
propanenitrile
reaction equation
2(species reacting
in the
slowest step)
SN2
S (substitution)
N(nucleophilic)
Слайд 15CN- ion with 2-bromo,2-methylpropane (SN1)
Nucleophilic substitution mechanism
2,2-dimethyl
propanenitrile
1(species reacting
in the
slowest step)
SN1
S (substitution)
N(nucleophilic)
reaction equation
Слайд 16Electrophilic Substitution
Nitration of benzene
C6H6
+ HNO3
C6H5NO2
+ H2O
Conditions / Reagents
concentrated HNO3
and concentrated H2SO4
50oC
mechanism
Where an H atom attached to an aromatic ring
is replaced by an NO2 group of atoms
Слайд 17electrophilic substitution mechanism (nitration)
2. Electrophilic attack on benzene
3. Forming the product
the
nitronium ion
HNO3
+ 2H2SO4
+ 2HSO4-
+ H3O+
reaction equation
and re-forming the catalyst
Слайд 18Bromination of benzene
C6H6
+ Br2
C6H5Br
+ HBr
Conditions / Reagents
Br2
and anhydrous AlBr3
25oC
Where an H atom attached to an aromatic ring
is replaced by a Br atom
electrophilic substitution
R = alkyl group
Слайд 19Electrophilic substitution mechanism
1. Formation of the electrophile
AlBr3
2. Electrophilic
attack on benzene
3. Forming the products
AlBr3
and re-forming the catalyst
bromobenzene
Слайд 20Alkylation of benzene
C6H6
+ RCl
C6H5R
+ HCl
Conditions / Reagents
RCl (haloakane)
and anhydrous AlCl3
0 - 25oC
Where an H atom attached to an aromatic ring
is replaced by a C atom
electrophilic substitution
to prevent further substitution
R = alkyl group
Слайд 21Alkylation example
Three steps in electrophilic substitution mechanism
1. Formation of
the electrophile (a carbocation)
AlCl3
With chloroethane
overall reaction equation
C6H6 + CH3CH2Cl
C6H5CH2CH3
+ HCl
Слайд 22Alkylation electrophilic substitution mechanism 2
2. Electrophilic attack on benzene
ethylbenzene
3. Forming the
product
AlCl3
and re-forming the catalyst
Слайд 23Acylation of benzene
C6H6
+ RCOCl
C6H5COR
+ HCl
Conditions / Reagents
RCOCl (acyl chloride)
and anhydrous AlCl3
50 oC
An H atom attached to an aromatic ring
is replaced by a C atom where C is part of C=O
electrophilic substitution
Слайд 24Acylation example
Three steps in electrophilic substitution mechanism
1. Formation
of the electrophile (an acylium ion)
AlCl3
With ethanoyl chloride
overall reaction equation
C6H6 + CH3COCl
C6H5COCH3
+ HCl
Слайд 25Acylation electrophilic substitution mechanism 2
2. Electrophilic attack on benzene
phenylethanone
AlCl3
3. Forming the products
and re-forming the catalyst
Слайд 26Nucleophilic Addition
RCHO
+ HCN
RCH(OH)CN
Conditions / Reagents
NaCN (aq)
and H2SO4(aq)
Room temperature and pressure
RCOR
+ HCN
RC(OH)(CN)R
supplies the CN- nucleophile
supplies H+
addition of hydrogen cyanide to carbonyls
to form hydroxynitriles
Слайд 27Nucleophilic Addition Mechanism
hydrogen cyanide with propanone
H+
NaCN (aq) is a source of
cyanide ions
CH3COCH3
+ HCN
CH3C(OH)(CN)CH3
H+
2-hydroxy-2-methylpropanenitrile
from H2SO4 (aq)
