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Written by Michael R-W, Forgotten Apple @ TSR

F324 Standard Answers

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

Why does Sodium Borohydride have to be aqueous to act as a reducing agent?


It dissolves in water so the ions dissociate NaBH4 -> Na+ + BH4
Dative bond breaks releasing Hydride ions (H-)in solution
What type of reaction takes place in reduction of a carbonyl and what type of bond fission occurs?
Nucleophilic addition; Heterolytic fission as both electrons go to one atom
Describe in words the mechanism of reduction of a carbonyl
Nucleophile is attracted to + C
The lone pair of electrons is donated to form a dative bond
The electron pair goes to the oxygen atom
Causing the bond to break

Written by Michael R-W, Forgotten Apple @ TSR

Carboxylic Acids and Esters


Why are short chain (<4 carbons) carboxylic acids soluble in water and longer chain not?

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

Written by Michael R-W, Forgotten Apple @ TSR


Two substituent groups attached to each C of the C=C are the same
Trans the two same groups attached are across, CIS when they are on the same side
What are the dangers of TRANS-Fats?
If a trans-fat is present:
Increasing bad cholesterol which increases the risk of coronary heart disease and strokes by
raising the low density lipoprotein levels like saturated fats do
Explain why triglycerides are soluble in non-polar solvents and not in water
There are Van Der Waals forces between triglycerides
There is Van Der Waals forces between triglycerides and non-polar solvent
Triglycerides cannot hydrogen bond to water (enough)
Because there are not enough suitable oxygen atoms/Long Hydrocarbons chains
Suggest a suitable alcohol for making biodiesel with fatty acids
Methanol or Ethanol as both are renewable -> Methanol from Plants; ethanol from
fermentation and also cheap. Alcohol is in excess to shift equilibrium towards the right

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

Sideways double overlap of p orbitals


between two carbon atoms
3 x Bonds
Localised electron density in bond
Both C-C and C=C bonds present
bonds between C-H

Sideways double overlap of p-orbitals


between adjacent carbon atoms both above
and below the plane of the ring
1 x bonding region
Delocalised Lower electron density in
region
Equal length C-C bonds present
bonds between C-H

Explain the relative resistance of bromination of benzene compared to alkenes (Reactivity


comparison)
In benzene electrons are delocalised, in alkenes they are localised between two C atoms
Benzene has lower electron density than alkenes
Benzene polarises and attracts Br2 less (not able to induce a dipole)
More energy needed to break the bond due to the delocalisation in benzene; More stable
In an alkylation reaction when CH3Cl reacts why is the electrophile CH3+ formed rather than Cl+
Cl more electronegative than C so when bond breaks by Heterolytic fission both electrons go
to Cl not CH3

Written by Michael R-W, Forgotten Apple @ TSR


Why is phenol more reactive than benzene?
Lone pair of electrons from O p-orbital is partially delocalised into the ring ( region)
region has higher electron density; region is activated
region more able to polarise electrophiles and attracts them more strongly
Phenol less stable/more reactive
Why do bromine atoms substitute the H atoms on positions 2, 4 and 6 in a reaction with phenol?
Most reactive hydrogens due to the position of the highly electronegative O atom
Uses of Phenols
Plastics, Antiseptics, disinfectants & Resins for Plants
Review the Evidence for a delocalised model of benzene
X-Ray Diffraction: Bond Lengths
c-c 0.153 nm; c=c 0.134nm; c-c in benzene 0.139nm
Not Separate C-C |C=C bonds/All equal length
H Hydrogenation

Benzene less exothermic than expected, when


compared the cyclohexene; more stable (-152kjmol-1
delocalisation enthalpy)
Reaction with Br2

Should react with Br2 at room temperature like


cyclohexane but benzene only reacts with Br2 at high
temp or in the presence of a halogen carrier
Not C=C so Benzene more stable

Deduce how many electrons are involved in the bonding in each structure and describe how their
arrangements are different.

6 Delocalised Electrons shared between


6 carbon atoms

4 Delocalised electrons shared between


5 Carbon atoms (one bonded 4 times)

Name types of material whose manufacture involves the nitration of benzene


Fibres, dyes and explosives
Pharmaceuticals

Written by Michael R-W, Forgotten Apple @ TSR

Nuclear Magnetic Resonance


What can be deduced from an a 13C NMR spectrum
The different types of carbon present, from chemical shift values
The possible structures of the molecule
What can be deduced from a High resolution Proton NMR spectrum
The different types of proton present, from chemical shift values
The relative numbers of each type of proton present from relative peak areas
The number of non-equivalent protons adjacent to a given proton from the spin-spin
splitting pattern, using the n+1 rule
The possible structures of the molecule
Why is TMS added?
TMS is a standard for chemical shift measurements and produces a peak at =0 (ppm)
What information can be deduced from an integration trace
Relative number of protons in each environment
Why are deuterated solvents used? State an example
So they do not produce a chemical shift/peak an example is CDCl3
What is the use of MRI and what is its relation to NMR?
MRI uses the same technology as NMR to obtain diagnostic information about internal
structures in body scanners
List Advantages of MRI
Harmless as uses low energy radio waves in contrast to high energy x-rays
Non-invasive (no cutting or incision required)
Patient does not feel anything
Can be obtained from most body parts
List Disadvantages of MRI
MRI is strong; anything magnetic can fly across room which is hazardous so scanning areas
must be cleared
Some patients should not be subjected to MRI Scan e.g. those with metallic implants that
would be attracted to scanner; patients with pacemakers as these are often affected by the
strong magnetic field
Describe a proton exchange using D2O
A proton NMR spectrum is run on the sample of the compound under investigation
A small amount of D2O is added to another sample; and another scan run
You can now compare the two spectra produced, to identify the NH, -OH by identifying
which peak/s are not present in the second spectra as these will have been removed
Explain how D2O can be used to confirm which protons are responsible for peak x
D replaces OH (or NH) proton/Protons are labile
The Peak for OH (or NH) protons disappears
Explain the number of peaks, splitting and types of proton in HOOCCH2CH2COOH in D2O
Number of peaks: 1, All four protons equivalent No splitting as protons are the same

Written by Michael R-W, Forgotten Apple @ TSR

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)

Written by Michael R-W, Forgotten Apple @ TSR


The alcohol would have a short retention time and the alkane would have a long retention
time because the alkane has a greater solubility in this solvent than an alcohol (As both have
Van Der Waals IMF)

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

Amino Acids and Chirality


Suggest how the carboxylic acid group and the primary amine group are able to react with each
other
-COOH donates H+ ion to amine group
N of amine group donate lone pair of electrons to H+
H+ from acid accepts lone pair
Dative coordinate bond is formed
What are the conditions for there to be e/z isomerism?
C=C which cannot rotate
Two different groups attached to each C of the C=C
Two of the substituent groups on either side of the C=C are the same
What are the conditions for there to be a chiral centre?
Four different groups attached
Advantages of a Single Optically pure isomer
Fewer Side effects
Increases the Pharmacological activity
Reduces the need/cost/difficulty in separating stereoisomers

Written by Michael R-W, Forgotten Apple @ TSR


Drug Doses are reduced
Method to prepare a single isomer
Using enzymes as biological catalysts As Single isomers are made naturally in living
systems, enzymes are being employed to mimic these natural processes
Chiral Synthesis Starting with naturally occurring chiral molecules such as amino acids and
sugars as starting materials can lead to production of one of a desired optical isomer
Chiral Catalyst Such as a transition metal complex resulting in the formation of one
optical isomer
Chiral Synthesis
Disadvantage of trying to remove optical isomer
Expensive
State the general formula for an amino acid use it to describe how amino acids can be combined to
give a variety of polypeptides and proteins
RCH(NH2)COOH
Repeat Unit; showing peptide bond
Polymerisation shown by open ends
Condensation: Loss of water; Variety due to different R groups/sequence of amino acids
Explain how two different dipeptides can be made from amino acid 1 and amino acid 2
Condensation reaction, with the loss of water
NH2 from one molecules reacts with COOH from another

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

Written by Michael R-W, Forgotten Apple @ TSR


Why are condensation polymers biodegradable?
May be hydrolysed at the ester or amide group
May be photodegradable due to the C=O bond which absorbs radiation
What are uses of Kevlar?
Kevlar is very strong/fire resistant so can be used as protective clothing for firefighters or
bullet proof vests
Uses of Polyesters
Polyesters and Polyamides are used as fibres in clothing
Uses of Biodegradable polymers Have bonds that can undergo hydrolysis
Polylactic acid, used for food packaging and disposable table ware is made from lactic acid
which is derived from corn starch
Polyglycolic acid is made from glycolic acid which is isolated from cane sugar and unripe
grapes. It is the polymer used in self dissolving surgical stitches
What are photodegradable polymers?
Synthetic polymers which become weak and brittle when exposed to light
Light sensitive additives within their structure catalyse their breakdown to waxy materials
and eventually CO2 and H2O
The carbonyl bond is in cooperated into the polymer backbone. The C=O group absorbs light
energy causing the backbone to breakdown naturally by fracturing the polymer chain
Explain what is meant by hydrolysis; use a peptide as an example to illustrate your answer
The breaking/splitting of a bond by its reaction with water
In a peptide the peptide bond in the compound is broken
Outline how an addition polymer forms from its monomers
bond breaks
Many molecules join together forming a long chain
Comment on the advantages and disadvantages of Addition Polymers
Many Uses
Durable
Release toxic chemicals when burned
Non-Biodegradable
Describe the ways in which chemists are trying to minimise the impact of the disadvantages
associated with addition polymer usage
Separation and recycling
Feedstock in other chemical reactions
Combustion for energy production
Developing biodegradable polymers from renewable raw materials e.g. Maize and starch

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