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A2 ORGANIC CHEMISTRY
MECHANISMS AND
REAGENTS.
KETONE
Lithium
tetrahydridoaluminate LiAlH4
[H
]
Sodium tetrahydridoborate
NaBH4
PRIMARY
ALCOHOL
SECONDARY
ALCOHOL
5m
in
Mechanism
Nucleophilic addition
The reducing agents produce the H- ion (the nucleophile).
The carbonyl bond is polar, due to oxygen being more
electronegative.
First Step is the hydride ion being attracted to the + carbon.
Second step, the product of first step gains a proton.
AQA A2 text
book, p66
HYDROXYNITRILES FROM
ALDEHYDES & KETONES
ALDEHYDE
KETONE
HC
N
HYDROXYNITRILE
KCN/H2SO4
Mechanism
Similar to making alcohols!
Nucleophilic addition
The reducing agents produce the CN- ion (the nucleophile).
The carbonyl bond is polar, due to oxygen being more
electronegative.
First Step is the cyanide ion being attracted to the + carbon.
Second step, the product of first step gains a proton from the
solvent or hydrogen cyanide.
AQA A2 text
5m
in
book, p68
AQA A2 text
book, p69
ESTER
WATER
AQA A2 text
book, p71
ESTER HYDROLYSIS
Acid Catalysed Hydrolysis
Reverse of esterification.
Dilute sulfuric acid or
hydrochloric acid.
Heat under reflux.
ESTER
WATER
Base-Catalysed Hydrolysis
Form a salt
Dilute strong base, sodium
hydroxide.
Heat under reflux.
This method is quicker than acid
ESTER
catalysed.
SODIUM
HYDROXIDE
AQA A2 text
book, p74
CARBOXYLIC ACID
ALCOHOLS
Heat with excess
dilute acid to
produce carboxylic
acid
SODIUM
CARBOXYLATE
ALCOHOLS
AQA A2 text
book, p74-75
PROPANE-1,2,3TRIOL
SODIUM
CARBOXYLATE
Three moles
produced
BIODIESEL
No need for Mechanism
Base catalysed Transesterification.
Heating vegetable oil with methanol and sodium hydroxide.
Produces methyl esters with long chains and propane-1,2,3-triol.
TRIACYGLYCEROL
SODIUM
HYDROXIDE
METHANOL
PROPANE-1,2,3TRIOL
METHYL ESTER
Three moles
Three moles
AQA A2 text
book, p75
ACYL CHLORIDES
Mechanism
Nucleophilic Substitution reactions. (two steps addition +
elimination)
Greater + on carbon due to Cl and O bond.
1st Step (addition) nucleophile attacks carbon + . Pair of electrons
in C=O is transferred to oxygen.
2nd Step (elimination) lone pair of electrons on oxygen forms C=O,
chlorine is eliminated. Hydrogen attached to oxygen atom breaks.
alcohol
water
CARBOXYLIC ACID
ESTER
ACYL CHLORIDE
N-SUBSTITUTED
AMIDE
AQA A2 text
book, p76-81
Primary
amine
ammon
ia
5
AMIDEm
in
ACID ANHYDRIDE
Synthesis
Dehydrate a carboxylic acid (P4O10
cat)
Mechanism
Same as acyl chlorides.
Secondary product is a
carboxylic acid.
water
CARBOXYLIC ACID
alcohol
ACID ANYDRIDE
N-SUBSTITUTED
AMIDE
AQA A2 text
book, p76-81
Primary
amine
ammon
ia
ESTER
5
AMIDEm
in
BENZENE
UNSTABLE
POSITIVELY
CHARGED
INTERMEDIATE
5
min
NITROBENZE
NE
PHENYLAMI
NE
Sodium nitrate(III),
HCl
Ice bath (chilled)
DIAZONIUM
SALT
WATER
SODIUM
CHLORIDE
No need for mechanism but you need to be able to draw compounds.
Diazonium salt reacts with phenylamine or other aromatic compounds to
produce azo dyes. HCl is also produced.
AQA A2 text
book, p92-93
TRINITROTOLUENE, TNT
No need for mechanism but need to be able to draw compounds.
METHYLBENZE
NE
AQA A2 text
book, p93
conc. HNO3
conc. H2SO4
2-METHYL-1,3,5TRINITROBENZENE
FIEDEL-CRAFTS ACYLATION
Mechanism
Generate the electrophile. Aluminium chloride and acyl chloride.
Electrophilic substitution(addition then elimination).
Electrophile is attracted to the delocalized electron.
C-H bond breaks and restores the stable delocalized electron
structure.
Aluminium chloride is regenerated whren [AlCl4]- reacts with H+.
BENZENE
AQA A2 text
book, p94
UNSTABLE
POSITIVELY
CHARGED
INTERMEDIATE
5
min
PHENYLETHANON
E
HYDROGEN
CHLORIDE
nucleophil
e
NH3
base
NH3
AMMONIUM
SALT
HALIDE
ION
AMINE
HALOALKA
AMMONIUM
NE
HALIDE
Mechanism
If you can do this you can describe
Amine acting as a nucleophile
Amine acting as a base
How to make secondary, tertiary amines and quarternary
ammonium salts
From Nitrile
Amine can be made by reducing nitrile
5
min
NITRILE
AQA A2 text
book, p100-107
4[H
]
LiAlH4
H2/Ni
AMINE
WATER
AMINE
6[H
]
NaOH
conc.HCl/Sn
or
conc.
HCl/Fe
AQA A2 text
book, p101
NH3+
INTERMEDIA
TE
ZWITTERIONS
Acting as a Base
Accepting protons.
NITROGEN IS
PROTONATED
AMINO ACID
H+
With Acid
HC
l
SALT
OH
NEGATIVE CHARGE ON
OXYGEN
SALT
WATE
R
Acting as an Acid
Donating protons.
AMINO ACID
With Base
AQA A2 text
book, p108-109
NaO
H
AQA A2 text
book, p110
DIPEPTIDE
WATER
Heat
Water
AMINO ACID
6 moldm-3 HCl
for 24 hours
AMINO ACID
DIPEPTIDE
AQA A2 text
book, p112
ADDITION POLYMERS
Mechanism
Addition ploymerisation
Involves one functional groups.
Carbon, carbon double bond.
Need to be able to identify repeating units
Taught in AS Chemistry Unit 2.
ALKENE
Monomer
AQA A2 text
book, p114-115
AQA AS text
book, p218-219
POLY(ALKENE
)
Polymer
POLYESTERS
Mechanism
Condensation ploymerisation
Involves two functional groups.
Polyesters are formed from a dicarboxylic acid and a diol.
Carboxyl group forms an ester link with the hydroxy group.
Need to identify ester link.
Identify the repeating units.
DICARBOXYLI
C ACID
POLYESTER
DIOL
WATER
AQA A2 text
book, p116-117
POLYAMIDES
Mechanism
Condensation ploymerisation
Involves two functional groups.
Polyamide are formed from a dicarboxylic acid and a diamines.
Hydroxyl group from dicarboxylic acid reacts with hydrogen
attached to nitrogen of polyamide.
Forms an amide link.
Need to identify amide link.
Identify the repeating units.
DICARBOXYLI
C ACID
POLYAMIDE
DIAMINE
WATER
AQA A2 text
book, p118-119
BIODEGRADABLE POLYMERS
Esters and amides can be hydrolysed by water, acids, alkalis and
enzymes.
This is the same for polyesters and polyamides.
Break ester link or amide link!
DICARBOXYLIC
DIAMIN
r
Wate
ACID
E
NaOH
SODIUM SALT
POLYAMIDE
DIAMIN
OF
E
DICARBOXYLIC
ACID
DICARBOXYLIC
DIAMIN
ACID
ACID
E
With polyesters the secondary product is a diol.