[PDF] [PDF] Mechanism Summary for A-level AQA Chemistry : - chemrevise

[PDF] Detailed Notes - Topic 33 Halogenoalkanes - AQA Chemistry A-level

Halogenoalkanes contain polar bondsas the halogens are more electronegative than carbon atoms This means electron density is drawn towards the halogen forming ∂+ and ∂- regions They must be shown with the lone electron pair and often a negative signindicating they are nucleophiles

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[PDF] Mechanism Summary for A-level AQA Chemistry : - chemrevise

with cyanide ions Elimination of Halogenoalkanes with ethanolic hydroxide ions Electrophilic Addition of Alkenes with Bromine Electrophilic Addition of 

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The halogen atom in a halogenoalkane molecule can be replaced by an –OH, – CN or –NH2 group These reactions are examples of nucleophilic substitution 

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CH3CH

HBrCH3CH

HOH-HO:+:Br-δ+δ-

CH3CHHCNCH3CH

HBr-NC:+:Br-δ+δ-

:OH-CCH

HCH3Br

HHCCHCH3HH

CCHCH3HHCH3Br

CCCH3HHCH3δ+δ-:Br-HBr

HOSO2OH

CCHHHCH3δ+δ--:OSO2OHC+CHHHCH3H

CCHHHCH3HOSO2OH

STEP ONE InitiationBr22Br.Essential condition: UV lightCH3CH3+ Br.HBr+CH3CH2.STEP TWO PropagationCH3CH2.+ Br2CH3CH2Br+ Br.STEP THREE TerminationCH3CH2.+ Br.CH3CH2BrCH3CH2.+CH3CH2.CH3CH2CH2CH3

Mechanism Summary for A-level AQA Chemistry

:CH3CCH3OH

HCH3CCH3O+H

H

HCC+CH3H

CH3CHHBr3HN:CH3CHHNH3+Br-

CH3CH

HNH2+H:NH3CH3CH

HNH2+ NH4Br

CH3CH2N+CH2CH3CH2CH3

H

Reaction 3 forming a tertiary amine

Reaction 4 forming a quaternary ammonium salt

CH3CH2NH+CH2CH3H

Reaction 2 forming secondary amineThe amine formed in the first reaction has a lone pair of electrons on thenitrogen and will react further with the haloalkane.CH3CHHBrCH3CH2NH2:CH3CH2NH2+CH2CH3Br-:NH3CH3CH2NHCH2CH3+ NH4BrDiethylamine

CH3CHHBr:CH3CH2NHCH2CH3

CH3CH2NCH2CH3CH2CH3

CH3CH2NH+CH2CH3CH2CH3

:NH3

CH2CH3Tetraethylammonium ion

triethylamine

Reaction 1 with ammonia forming primary amine

Nucleophilic Addition-Elimination Mechanism

CClCH3OCH2CH3O

H

CClCH3NHCH2CH3O

H CHCH3CH3ONucleophilic Addition MechanismH+fromwater or weak acid

CH3CCH3O:H-δ+δ-:H+

CHCH3CH3OH-Nucleophilic Addition MechanismH+fromsulphuricacid

CH3CCH3O:CN-δ+δ-:H+-CCNCH3CH3O

CCNCH3CH3OH

CClCH3OHO

HCH3COCl

CH3COOH:δ+δ-:-

OHH+CH3COCl:δ+δ-+

OCH2CH3H-:

CH3COCH2CH3O-CClCH3NH2O

HCH3COCl:δ+δ-+:NH3CH3CNH2O

CH3COCl:δ+δ-+:

NHCH2CH3HCH3CNHCH2CH3OElectrophilic Substitution

+H+HNO2 NO2 Equation for Formation ofelectrophileHNO3+ 2H2SO4NO2++ 2HSO4-+ H3O+

H++HSO4-H2SO4COCH3

CH3C+OHCCH3OEquation for Formation of the electrophile.AlCl3+ CH3COClCH3CO+AlCl4-Electrophilic Substitution

Nucleophilic Addition-Elimination Mechanism

Nucleophilic Addition-Elimination MechanismNucleophilic Addition-Elimination Mechanism-

Mechanism Summary for A-Level AQA Chemistry

NuSub NuSub ester

Nu AddNu Add

Nu Add

NuSub Esters andamides can behydrolysed byNaOH and acids

ReactionSummary for A-level AQA Chemistry

NO2conc nitric acid +conc sulphuric acidElectrophilicsubstitution COCH3 acyl chloride in the presenceof anhydrous aluminiumchloride catalystElectrophilic substitution

NH2Sn and HClreduction

NHCOCH3CH3COClNucleophilic add-el

CHOCH3

HNu Add

NHCH3CH3ClNu sub

CO CH3

HCNNu Add

COH

CH3CH2NH2

Aromatic synthetic routes

CHCH3OCOCH3

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