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Mechanism Summary For AS AQA Chemistry: HO: NC

1. The document summarizes several different reaction mechanisms for organic chemistry including nucleophilic substitution, elimination, electrophilic addition, free radical substitution, and nucleophilic addition reactions. 2. Key reaction mechanisms include nucleophilic substitution of haloalkanes with hydroxide ions, cyanide ions, and ammonia. Elimination reactions of haloalkanes are also summarized. 3. Electrophilic addition reactions of alkenes using bromine, hydrogen bromide, and sulfuric acid are outlined. Free radical substitution of alkanes using bromine and UV light is described as a three step process. 4. Nucleophilic addition mechanisms involving addition of hydroxide/

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0% found this document useful (0 votes)
256 views4 pages

Mechanism Summary For AS AQA Chemistry: HO: NC

1. The document summarizes several different reaction mechanisms for organic chemistry including nucleophilic substitution, elimination, electrophilic addition, free radical substitution, and nucleophilic addition reactions. 2. Key reaction mechanisms include nucleophilic substitution of haloalkanes with hydroxide ions, cyanide ions, and ammonia. Elimination reactions of haloalkanes are also summarized. 3. Electrophilic addition reactions of alkenes using bromine, hydrogen bromide, and sulfuric acid are outlined. Free radical substitution of alkanes using bromine and UV light is described as a three step process. 4. Nucleophilic addition mechanisms involving addition of hydroxide/

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john m
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Mechanism Summary for AS AQA Chemistry

Nucleophilic Substitution of Haloalkanes Nucleophilic Substitution of Haloalkanes


with aqueous hydroxide ions. with cyanide ions.
H H H H
δ+ δ- δ+ δ-
H3C C Br H3C C OH + :Br - H3C C Br H3C C CN + :Br -

-HO: -NC:
H H H
H

Nucleophilic Substitution of Haloalkanes with ammonia


H H Elimination of Haloalkanes with ethanolic
H :Br -
hydroxide ions
δ+ δ- +
CH3 CH2 C Br CH3 CH2 C N H H H H H
3HN:
H H CH3 C C H CH3 C C H
H
:NH3
+ Br - + H2O
Br H
H
:OH-
CH3 CH2 C NH2 + NH Br
4
H

Electrophilic Addition of Alkenes with Bromine Electrophilic Addition of Alkenes with hydrogen
bromide
H H H H H H H H
H H
+
C C H C C H H C C H H3C C C CH3 +
H3C C C CH3
H H Br δ+
Br δ+ Br Br H H
:Br - δ- :Br -
Br
Br
δ-
H H

Electrophilic Addition of Alkenes with sulphuric acid H3C C C CH3

H H H Br H
H
+
H3C C C H H3C C C H

δ+ H Free Radical Substitution of Alkanes with Bromine


H -:OSO
2OH
OSO 2OH STEP ONE Initiation
δ- H Essential condition: UV light
H
Br2  2Br
.
H3C C C H
H STEP TWO Propagation
OSO 2OH . .
CH3CH3 + Br  HBr + CH3CH2
.
CH3CH2 + Br2  CH3CH2Br + Br
.

STEP THREE Termination


.
CH3CH2 + Br  CH3CH2Br
.
.
CH3CH2 + CH3CH2  CH3CH2CH2CH3
.

N Goalby chemrevise.org 1
Mechanism Summary for A2 AQA Chemistry
Nucleophilic Addition Mechanism Nucleophilic Addition Mechanism
H+ from water or weak acid
O
δ-
O:
- H+ δ-
H+ from sulphuric acid

+
O
O: - H+
Cδ H3C C CH3
H3C CH3 C δ+ H3C C CH3
H
:H- H3C CH3
CN
O H :CN- O H
H3C C CH3 H3C C CH3
H CN

Nucleophilic Addition –Elimination Mechanism Nucleophilic Addition –Elimination Mechanism


O δ- :O- δ- :O
-
O
CH3 C δ+ + +
H3C C OH CH3 C δ+
H3C C OCH2CH3
Cl Cl
:OH Cl H
Cl H
: OCH CH
O 2 3
H O
CH3 C H
C
OH H3C OCH2CH3

Nucleophilic Addition –Elimination Mechanism Nucleophilic Addition –Elimination Mechanism


δ- : O- δ-
O : O-
O
+ CH3 Cδ+ +
CH3 C δ+ H3C C NH2 H3C C NHCH2CH3
Cl
Cl Cl H :NHCH 2CH3 Cl H
: NH3 O O
H
C C
H3C NH2 H3C NHCH2CH3

Electrophilic Substitution Electrophilic Substitution


Equation for Formation of electrophile Equation for Formation of the electrophile.
HNO3 + 2H2SO4  NO2+ + 2HSO4- + H3O+ AlCl3 + CH3COCl  CH3CO+ AlCl4-

NO 2 O O
NO2+
+ C CH3
H C CH3
+
H
+

NO 2 O
C
+ H+ CH3

H+ + HSO4- H2SO4 H+ + AlCl4-  AlCl3 + HCl

N Goalby chemrevise.org 2
Nucleophilic Substitution reactions of ammonia/amines

Reaction 1 with ammonia forming primary amine


H H
+
H3C C Br H3C C NH3 Br -
H
H
3HN:

H H
+
H3C C NH2 H3C C NH2 + NH4Br
:NH3
H H H

Reaction 2 forming secondary amine

The amine formed in the first reaction has a lone pair of electrons on the
nitrogen and will react further with the haloalkane.
H
+
H3C CH2 NH2 CH2 CH3
H3C C Br Br -
H
:

CH3CH2NH2
+
H3C CH2 NH CH2 CH3 H3C CH2 NH CH2 CH3 + NH4Br
:NH3
H Diethylamine

Reaction 3 forming a tertiary amine

H CH3
CH2
H3C C Br +
H3C CH2 NH CH2 CH3
H
:

H3C CH2 NH CH2 CH3


CH3
CH2 CH3
+ CH2
H3C CH2 N CH2 CH3
:NH3 H3C CH2 N CH2 CH3
H triethylamine

Reaction 4 forming a quaternary ammonium salt


H

H3C C Br CH3
CH2
H +
H3C CH2 N CH2 CH3
:

H3C CH2 N CH2 CH3 CH2


CH2 CH3
CH3
Tetraethylammonium ion

N Goalby chemrevise.org 3
KOH aqueous
heat under reflux
Nu Sub
dihaloalkane diol
poly(alkene)
high pressure
catalyst Br2, Cl2 room temp
EAdd
alkane
alkene
Br2, Cl2
Step 1 H2SO4 UV light
EAdd Fr Sub
conc. H2SO4 or
Step 2 H2O warm
conc. H3PO4
hydrolysis Elimination,
dehydration
KOH aqueous
heat under reflux
NuSub
alcohol haloalkane
NaBH4
NaBH4 Alcoholic NH3
Red Nu Add KCN in ethanol/
Red Nu Add heat under
water mixture heat pressure
under reflux NuSub
NuSub
If secondary
If primary Na2Cr2O7/H+ LiAlH4 in ether
Na2Cr2O7/H+ heat nitrile reduction 1o amine
heat and distill oxidation
partial ox haloalkane
Caboxylic acid + NuSub
H2SO4
heat
aldehyde ketone esterification 2o amine Acyl chloride
room temp
3o amine Nu add/elim
NaCN + H2SO4 Quaternary salt
Nu Add
(If primary) Na2Cr2O7/H+
heat under reflux + excess Esters and secondary
oxidising agent hydroxynitrile amides can be
amide
Oxidation hydrolysed by
NaOH and acids

Alcohol + H2SO4 ester 1o amine


carboxylic acid heat room temp
esterification Nu add/elim

Alcohol
room temp Primary
H2O room temp Nu add/elim
Nu add/elim amide
Acyl chloride/ NH3 room temp
Nu add/elim
acid anhydride

N Goalby chemrevise.org
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