Beruflich Dokumente
Kultur Dokumente
Carbonyls
Outline a simple chemical test to detect the presence of a carbonyl and determine its identity
Add 2,4-Dinitrophenylhydrazine (2,4-DNP)
Orange Precipitate hydrazone will form if a carbonyl is present (Aldehyde or Ketone)
To determine the identity purify the hydrazone precipitate by recrystallization
Measure the melting point of the purified precipitate
Compare the melting point with data table values to identify the aldehyde or ketone
Outline a simple chemical test to distinguish between a Ketone and an aldehyde
Add Tollens Reagent (Ammoniacal Silver Nitrate) Warm in water bath to 60C
Aldehyde A silver mirror will form as Silver reduced Ag+(aq) + e- Ag(s)
Ketone No visible observation
Describe the formation of a bond in a carbonyl C=O bond and compare to alkene
Sideways double overlap of P orbitals both above and below plane of molecule
Electrophiles will be repelled/nucleophiles attracted to Cd+ / -bond electrons are
unavailable due to polarisation
Highly polar C=O bond and O-H bonds in carboxylic acid molecules for H bonds with polar
water molecules
As the number of carbons increases a greater proportion of the molecule is non polar which
is hydrophobic. This does not attract H2O and cannot form H bonds with H2O molecules.
The more Os with lone pairs on a compound the more soluble
Describe a simple chemical test to differentiate a carboxylic acid from phenol and an alcohol
Add a carbonate, the carboxylic acid will react the others wont
Weak Acid
Carbonate
Base
Metal
Carboxylic Acid
Phenol
Alcohol
Why is the method of using an anhydride to create an ester more favourable than alcohol + C.A?
Better Yield as irreversible reaction
Only warm conditions required rather than heat/reflux/catalyst so cheaper
What are common uses of esters?
Used as perfumes/flavourings as they have a fruity smell
What are important functions of Fats in the body?
Protect organs
High energy store
Provide Insulation
Why are saturated fats solid at room temperature?
Higher melting point
More intermolecular forces between molecules
More energy required to overcome intermolecular forces
Why do unsaturated fats have lower melting points than saturated fats?
Lower Boiling point
Less intermolecular forces between molecules #
Less energy to overcome
Explain how CIS-TRANS isomerism comes about in an unsaturated fat
C=C which cannot rotate
Two different groups attached to each carbon of the C=C
Arenes
Compare the Kekule and delocalised models for benzene in your answer, include reference to p
orbital overlap forming bonds and use diagrams
Kekule
Delocalised
Deduce how many electrons are involved in the bonding in each structure and describe how their
arrangements are different.
Describe and explain the different ways that a high resolution NMR spectrum can give information of
a molecule
Chemical Shift values give the type of proton environment
The number of peaks gives the number of different proton environments
Relative peak areas give the number of protons in each environment
Splitting gives the number of adjacent protons
o Using n+1 rule so e.g. Doublet means one proton on adjacent carbon
D2O can be used to identify OH and NH protons
Chromatography
In TLC how can you use the chromatogram to identify the compounds
Measure how far each spot travels relative to the solvent front
Calculate the Rf value Using Equation =
Compare the Rf value found with data table values for the type of compound
State disadvantages of chromatography
Similar compounds have similar retention times/Rf values due to similar structutes
Unknown compounds have no reference retention times/Rf values
It can be difficult to find a solvent that separates all the components in a mixture (too
soluble will not retain on the stationary phase and if not soluble enough then components
will hardly move)
Why may a TLC contain more compounds than spots
One may contain two or more compounds; particularly if the spot is over a large region
Discuss the advantages of GC-MS (Gas Chromatography-Mass Spectroscopy)
Provides a far more analytical tool than chromatography alone
Gas chromatography separates but cannot conclusively identify components
Gas Chromatography can give the relative proportions from the relative peak areas
Mass Spectroscopy identifies structures by a computer comparing fragment ions with a
spectral database
Where is GC-MS Used?
Forensics, Environmental Analysis, airport security and space probes
Describe (Solid) Thin Layer Chromatography (TLC)
Stationary Phase: Solid, Separation by adsorption
Mobile Phase: Liquid e.g. Solvent
Describe (Liquid or Gas) Gas Chromatography
Stationary Phase: Liquid or Solid (on a solid support) separation by relative solubility into
liquid or adsorption onto solid
How do the relative retention times of two esters, an alkane and an alcohol compare giving an
indication of the length of their retention times (using an alkane stationary phase)
The two esters will have similar retention times as they have similar structures (both C=O)
Mass Spectrometry
State a spectroscopic method to determine the molecular mass of a sample of a substance and how
you would obtain it with this method
Mass Spectrometry
Highest m/z (mass to charge ratio) value is equal to the molecular mass of the substance
Determine the molecular mass from a spectrum
M+ peak at m/z = ***; Then identify a fragment ion
Amines
What are disadvantages of nitration of hagenoalkane; what is a way to minimize this?
Further substation can occur forming secondary and tertiary amines
Use an excess if NH3 to ensure this acts as nucleophile
Why do Amines act as bases?
Lone pair of electrons on N accepts a proton/H+
Lone pair of electrons on N can be donated to H+;H+ accepts lone pair
Forms Dative coordinate bond
Why must a diazonium salt/ion be formed at a temperature <10C
Diazonium salt/ion is very unstable and will readily hydrolyses to form phenol
Why must HNO2 be created in Situ using HCl and NaNO2 when forming a diazonium salt/ion?
Nitrous acid decomposes very readily and so is always made in situ
State the Uses of an Azo
A Dye/Pigment/Colouring
Synthesis
Synthetic and Natural Comparison
Molecules prepared synthetically in the laboratory often contain a mixture of optical isomers
Molecules of the same compound produced naturally by enzymes in living systems will often
be present as one optical isomer only
Synthesizing only one optical isomer
Increase costs due to the difficulty in separating the optical isomers
Reduces the possible side effects and improves pharmacological activity
Modern Synthesis of Pharmaceuticals with a single optical isomer is carried out:
Using enzymes or bacteria which promote stereoselectivity as enzymes themselves are chiral
Using chemical chiral synthesis or chiral catalysts
Using natural chiral molecules, such as L-amino acids or sugars as starting materials
State the disadvantages of synthesising a pharmaceutical compound containing a mixture of optical
isomers (that is both D- and L- optical isomers)
Increased costs due to difficulty in separating the optical isomers.
Reduced pharmacological activity
Possible (harmful) side effects, e.g. Thalidomide.
Increased drug doses.
Polymers
Why are biodegradable polymers increasing in importance?
Minimize environmental waste and Reduce Landfill Waste
Polymers produces toxic gases when burnt