WHOLE ORGANIC SYNTHESIS (LOL) Flashcards
How to perform reflux and when is it used
if you need to heat volatile liquids so that reactants or products are not lost as they will evaporate and condense back into the flask
use a heating mantle if liquids are flammable to heat a round bottom flask that is attached to a condenser with water flowing upwards
How to perform distillation and when is it used
used to separate substances with different boiling points, or to extract a chemical before it reacts any further
gently heat mixture using a heating mantle with a thermometer to control temperature, product will evaporate out and condense using a water condenser into a flask on the other side
When is filtration used and how
used to separate solids from liquids
place a filter paper disc in a Buchner funnel and wet it to create a seal, place funnel on top of flask, then pour the mixture into the funnel with a vacuum line on to thoroughly separate the liquid out
vacuum creates reduced pressure which pulls the liquid through
solid can be recrystallized to purify further
When is recrystallisation used and how to do it
used to purify solids using a very carefully chosen solvent
add just enough hot solvent to dissolve impure solid to give a SATURATED SOLUTION of impure product
allow solution to cool down which causes crystal formation
the impurities will remain dissolved in solution as they take longer to crystallise as there is less
then filter to get purified solid crystals and wash these with very cold solvent then dry crystals
How to measure boiling point of substance and why
what values signify impurities
what is an issue with identifying boiling points
can help to detect impurities
can determine boiling point using distillation by gently heating and measuring temperature that it distils
then compare value to a data book which can signify impurities, higher boiling point or a range of temperatures shows impurities
some organic compounds have similar boiling points so other analytical techniques must be used
Alkane functional group, properties and typical reactions
C-C
unreactive, non-polar bond
typically radical substitution
Alkene functional group, properties and typical reactions
C=C
electron rich double bond, non-polar bond
typically electrophilic addition
Alcohol functional group, properties and typical reactions
C-OH
lone pair on oxygen can act as nucleophile, Polar C-O bond
typically esterification and nucleophilic substitution or dehydration/elimination
Aromatic compound functional group, properties and typical reactions
C6H5-
delocalised electron ring, stable compound
typically electrophilic substitution
Aromatic compound functional group, properties and typical reactions
C6H5-
delocalised electron ring, stable compound
typically electrophilic substitution
Haloalkane functional group, properties and typical reactions
C-X
polar C-X bond
typically nucleophilic substitution and elimination
Nitrile functional group, properties and typical reactions
C-CN
electron deficient carbon centre
typically reduction and hydrolysis
Amine functional group, properties and typical reactions
C-NH2
lone pair on N is basic, can act as a nucleophile
typically undergo nucleophilic substitution and neutralisation
Aldehyde and ketone functional group, properties and typical reactions
C=O
polar C=O bond
typically undergo nucleophilic addition, oxidation, reduction
Carboxylic acid functional group, properties and typical reactions
COOH
electron deficient carbon centre
typically esterification and neutralisation
Ester functional group, properties and typical reactions
RCOOR
electron deficient carbon centre
typically undergo hydrolysis
Acid anhydride functional group, properties and typical reactions
RCOOCOR
electron deficient carbon centre
typically esterification
Acyl chloride functional group, properties and typical reactions
COCl
electron deficient carbon centre
nucleophilic addition-elimination, friedel crafts acylation
What is an addition reaction and what functional groups can this occur in
double bond is broken and 2 molecules join to form a single product
C=C
C=O
COOH
What is a substitution reaction and what functional groups can this occur in
A functional group is exchanged for another
C-X
C-OH
Benzenes
What is an elimination/Dehydration reaction and what functional groups can this occur in
A double bond usually formed when functional group is removed and released as part of a smaller molecule
C-X eliminates HX
C-OH eliminates H2O
What is a condensation reaction and what functional groups can this occur in
2 molecules join and a small molecule is released (H2O or H-Cl usually)
COCl
COOH
CONH2
C-OH
What is a hydrolysis reaction and what functional groups can this occur in
2 smaller molecules are formed by splitting a larger one with water
polyamides, polyesters
What is an oxidation reaction and what functional groups can this occur in
Gaining of oxygen or loss of a hydrogen (theoretically loss of electrons)
C-OH –> C=OH –> COOH
What is a reduction reaction and what functional groups can this occur in
Normally loss of oxygen or gain of hydrogen (theoretically gain of electrons)
COOH –> C=OH –> C-OH
Alcohol –> aldehyde
K2Cr2O7, H2SO4
heat primary alcohol under distillation
Aldehyde –> alcohol
NaBH4 in methanol and water
Aldehyde –> Carboxylic acid
K2CR2O7, H2SO4
heat under reflux
Alcohol –> ketone
K2CR2O7, H2SO4
heat secondary alcohol under distillation
Alcohol –> haloalkane
NaX, H2SO4
20 degrees
Alcohol –> alkene
Conc H2SO4/H3PO4
heat
Alkene –> alcohol
Steam, H3PO4 catalyst
60 atm
300 degrees
Alkene –> dihaloalkane
X2
20 degrees
Alkene –> haloalkane
HX
20 degrees
Haloalkane –> alkene
KOH, ethanol
heat under reflux
Haloalkane –> alcohol
Warm NaOH, H2O
heat under reflux
Alkane –> haloalkane
X2
UV light
ketone –> alcohol
NaBH4, methanol, water
Alkene –> alkane
Hydrogen, Nickel catalyst
150 degrees
Haloalkane –> primary amine
NH3
heat
Haloalkane –> 2nd/3rd amine
NH3
heat
Carboxylic acid –> ester
Alcohol, Conc H2SO4
heat
COOH –> Acid chloride
SOCl2
Acid chloride –> COOH
H2O
20 degrees
Acid chloride –> ester
Alcohol
20 degrees
Aldehyde/ketone –> Hydroxynitrile
KCN, H2SO4
20 degrees
Hydroxynitrile/nitrile –> amine
LiAlH4 + dilute H2SO4
or
Hydrogen, nickel catalyst
high temp and pressure
Haloalkane –> nitrile
KCN, ethanol
heat under reflux
Acid chloride –> primary amide
NH3
20 degrees
ester –> COOH
Dilute H2SO4, H2O
heat under reflux
or
NaOH
heat under reflux
Benzene –> nitrobenzene
Nitration
Conc H2SO4 + HNO3
less than 55 degrees
Nitrobenzene –> phenylamine
Reduction
Conc HCl, Sn
heat under reflux with NaOH
Benzene –> Phenylketone
Acylation
Acyl chloride, AlCl3 catalyst, heat under reflux in anhydrous conditiions
Benzene –> Halobenzene
Halogenation
X2, AlCl3 catalyst in warm conditions
Benzene –> alkylbenzene
Alkylation
Haloalkane, AlCl3 catalyst
heat under reflux
Phenol –> sodium phenoxide
NaOH
20 degrees
Phenol –> 2,4,6 tribromophenol
Br2
20 degrees
Phenol –> Phenyl ester
Acyl chloride
20 degrees
