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b
c
Draw a flow chart showing the reaction pathways for the preparation of aspirin
from salicylic acid using:
i ethanoic acid
ii ethanoic anyhdride
Explain why the pathway using ethanoic anhydride is preferred over the one
using ethanoic acid.
Which pathway could be considered greener because it produces the least amount
of waste?
A1.
a
b
c
Q3.
Why do the instructions on prescription antibiotics tell you to complete the whole
course of tablets?
A3.
At the point when the symptoms of an infection disappear there may still be bacteria
present in the body. If you cease taking antibiotics at this stage the bacteria may start
multiplying again and the infection could return.
Q4.
Penicillin V is more stable in the presence of stomach acid so can be given to the
patient in tablet form. Penicillin G is more potent but has to be given in the form of an
injection, requiring a visit to a medical clinic.
What information about the molecular structure of a drug does each of these analytical
techniques provide?
a infrared spectroscopy
b nuclear magnetic resonance spectroscopy
c mass spectroscopy
A5.
Medicinal proteins such as insulin are administered by injection. Suggest why they
cannot be given orally as tablets or capsules.
A6.
Since insulin is a proteinif it was given orally the substance would be broken down
in the process of digestion before it could be absorbed.
Why is the sodium salt of acetylsalicylic acid more soluble than normal aspirin?
A7.
Sodium acetylsalicylic acid is more soluble in water than acetylsalicylic acid because
it dissociates into ions (Na+ and the acetylsalicylate anion) which then attract water
molecules to form solvation sheaths around them.
Q8.
Aspirin blocks the action of the enzymes that control the production of prostaglandins
substances that cause the blood vessels to constrict resulting in heat building up in
the body to cause fever. Prostaglandins also make it easier for water to pass from
blood capillaries into tissues where it causes swelling and pain.
Q9.
ethanoic acid, CH3COOH. Note the similarity between this reaction and the
reaction for the synthesis of aspirin.
molar mass of atoms used in the products
Percentage atom economy =
100
molar mass of all reactants
123
=
100
109 + 102
= 58%
Q10.
a
A10.
a
The COX-2 inhibitors only works on the enzymes that are present at the site of
inflammation and not on those present in the stomach. Hence it does not cause
stomach irritation or bleeding.
Vioxx was withdrawn in 2004 because of concern that it has adverse side effects
and may lead to the development of heart disease or stroke.
Q11.
From the description of the use of the Australian native plant with the Aboriginal
name of bunaangu, what active ingredient might be present to give it these medicinal
properties?
You only eat the sap of the bunaangu. It has a bitter taste. You boil it up to drink. It
helps toothache and a bad chest.
A11.
From the description of the bitter taste of bunaangu and the symptoms that it helps to
relieve, it seems as though the plant might be a source of salicin or possibly salicylic
acid.
Q12.
The website Aspirin Adventures provides an easy to read summary of various pain
killers. http://www.chemheritage.org/educationalservices/pharm/asp/asp00.htm
Q13.
Codeine, morphine and heroin are drugs derived from the opium poppy. The
molecular structure of these drugs is shown in Figure 14.26. Identify the part of each
molecular structure that is common to all three drugs. How does the structure of these
molecules differ?
Figure 14.26
Molecular structures of codeine, morphine and heroin. Cautionit is not possible to convert
codeine into morphine or heroin by any simple laboratory process.
Different functional groups are attached to the benzene rings in each structure. Small
changes to the molecular structure can result in significant changes to chemical or
biochemical activity.
Q14.
Advantages: convenient source of the medicinal protein that can be grown rather than
produced via chemical synthesis. Could be included in the diet rather than having to
be taken as a medication or could be used to supplement inadequate food supplies.
Disadvantages: the effects of adding a medicinal protein to food has not been
subjected to long-term studies. Also the modified gene may be transferred to other
plants and result in unwanted harmful effects.
Q15.
Use the web to find out about the diseases that are treated by the following medicinal
proteins:
a growth hormone
b interferon
c monoclonal antibodies
A15.
a
b
c
Growth hormone is used to treat children who fail to grow at a normal rate due to
growth hormone deficiency.
Interferon is used to treat hepatitis C.
Specific monoclonal antibodies can be used to treat certain types of cancer of the
kidney, leukaemia or lymphoma. Cytotoxic (cancer killing) substances are joined
to the antibody and the resulting complex is given to the patient. The antibody,
with the cytotoxic agent attached, then binds only to the cancer cells and
eliminates them. Sometimes just the antibody itself is sufficient to trigger the
bodys normal defence mechanism and stimulate it to eliminate the cancer cells.
Q16.
Illustrate, using aspirin as an example, how biochemists modify the structure of drugs
to eliminate undesirable side effects.
A16.
Salicylic acid was used as a pain killer but found was to found to cause bleeding of
the stomach walls. Its structure was modified by reaction salicylic acid (aspirin) with
ethanoic acid to form the ester, acetylsalicylic acid which while an effective pain
killer did not have this side effect. A soluble form of aspirin was developed by
converting the carboxylic acid functional group to a sodium salt.
The active ingredients in drugs such as aspirin consist of organic molecules that can
be made via a chemical pathway from some fairly simple feedstock. However,
substances such as insulin are proteins that are made by the body. It would be very
difficult to manufacture such a large molecule via a chemical pathway. Instead, they
are made by adapting the structure of a related protein obtained from a biological
source.
The smallest molecule in which homologous series must contain two carbon atoms?
A an alkane
B an alkanol
C an alkene
D an alkanoic acid
A1.
C. There is a double bond between two carbon atoms in alkenes. The first members of
the other homologous series, methane, methanol and methanoic acid all contain
1 carbon atom.
Q2.
B. It may assist you to draw a full structural formula. This molecule is an alkane as
there are no multiple bonds, therefore the name ends in ane There are 5 carbon atoms
in the longest chain name must end in pentane. There is a methyl group on the second
carbon atom from the end. This is represented as 2-methyl. The full name is
2-methylpentane.
Q3.
A. The alkanols have higher boiling points as the strength of the intermolecular forces
are greater. The strength of hydrogen bonding in alkanols is greater than those in
chloroalkanes. Only dispersion forces act between alkane molecules.
Which of the following statements are true of the homologous series of primary
alkanols?
I The members differ by one CH2 unit.
II They are all strong bases.
III They can be oxidised to form carboxylic acids.
A I and II
B II and III
C I and III
D I, II and III
A4.
A. Ethene, CH2CH2, will undergo an addition reaction with bromine. The double bond
is broken and a bromine atom bonds to each carbon atom to form 1,2-dibromethane.
Q6.
A
B
C
D
ethanol
methanol
ethanoic acid
methanoic acid
A8.
10
Consider the following molecular structures of substances that all function as drugs.
(Chemically inactive hydrogen atoms have been omitted for clarity.)
The substances that are expected to have similar pharmaceutical effects are:
A I and II
B II and III
C I and III
D I, II and III
A9.
C. Compounds I and III have similar molecular structures and would be expected to
have similar pharmacological effects.
Q10
11
A
B
C
D
2,4-dimethylhexane
2-methyl-4-ethylpentane
2-ethyl-4-methylpentane
1,1,3-trimethylpentane
A11.
A. The substance is an alkane. The longest chain contains 6 carbon atoms. There are
methyl side chains on the 2nd and 4th carbon atoms.
Q12.
A carboxylic acid with five carbon atoms per molecule could have the formula:
A C5H11COOH
B CH3(CH2)4COOH
C CH3CH2CH2CH2COOH
D C3H7COOCH3
A12.
A
B
C
D
The 13C NMR spectrum of compound I has three peaks, and that of compound II
has two peaks.
The low resolution 1H NMR spectrum of I has four peaks, and that of II has three
peaks.
The mass spectrum of both will show a peak at a mass-to-charge ratio of 60.
The fingerprint region of the IR spectra will be identical for both compounds.
A13.
D. The compounds shown are propan-1-ol and propan-2-ol. They are isomers. The
fingerprint region of the IR spectra of these compounds would be different as their
structures are different.
12
CO(NH2)2
II
C3H8O3
VI
C2H5NO2
III
CO2
VII
C3H7NO2
IV
C17H35COOH
VIII
Q14.
From the list, identify two molecules that would react together to form a dipeptide.
A II and III
B III and IV
C IV and VI
D IV and II
A14.
When a saturated fat undergoes hydrolysis, two products that might be formed are:
A VI and VIII
B I and III
C V and VI
D II and VIII
A15.
A. Fats hydrolyse to form fatty acids (V and VIII) and glycerol (VI); molecule VIII
has only single C-to-C bonds in the hydrocarbon chain (CH3(CH2)16COOH) and is a
saturated fatty acid, formed from a saturated fat.
Q16.
When starch is formed from glucose, the condensation reaction that occurs involves:
A a carboxyl functional group and an amino functional group
B two hydroxyl functional groups
C a hydroxyl functional group and a carboxyl functional group
D a hydroxyl functional group and an amino functional group.
13
Q17.
Olive oil contains a high proportion of oils made from a fatty acid called oleic acid.
The formula of oleic acid is C18H34O2. The number of carbon-to-carbon double
covalent bonds in oleic acid is:
A 0
B 1
C 2
D 3
A17.
When a protein, such as insulin, is formed, the condensation reaction that occurs
involves:
A a carboxyl functional group and an amino functional group
B two hydroxyl functional groups
C a hydroxyl functional group and a carboxyl functional group
D a hydroxyl functional group and an amino functional group.
A18.
A. The amino group, NH2, of one amino acid reacts with the carboxyl functional
group, COOH, of the other to form a peptide link, NHCO.
14
Protein molecules are formed by condensation reactions between amino acids. The
secondary structure of many proteins is a helical shape. The type of chemical bond
responsible for maintaining this shape is:
A hydrogen bonds
B iondipole bonds
C ionic bonds
D covalent bonds.
A19.
A. Hydrogen bonds form between the positive dipole of an NH+ group in one
peptide link of the protein and the negative dipole of a C=O group in another
peptide link of the same protein molecule as shown in the diagram.
15
A20.
a
b
c
d
Alkenes have a double covalent bond that allows them to make a range of useful
addition compounds.
i Brown bromine solution becomes colourless.
ii C2H4(g) + Br2(aq) CH2BrCH2Br(l)
i Infrared spectroscopy
ii Characteristic absorption of C=C bond at 2070 to 2250 cm1
i addition polymerisation
ii n CH2CH2 ~[CH2CH2]n~
iii polyethene
Q21.
a
b
16
i
ii
i
ii
i
ii
Q22.
a
b
Crude oil consists mainly of alkanes of varying molecular sizes. What feature of
the intermolecular forces of alkanes allows the alkanes to be separated into
fractions at an oil refinery?
Ethanol is an alternative biochemical fuel to petrol.
i Draw the structural formula of ethanol.
ii Why does ethanol have an affinity for water whilst the alkanes in petrol
do not?
E10 petrol contains 10% ethanol. Outline the environmental advantages using
E10 petrol.
A22.
a
The dispersion forces between the alkane molecules increase as the size of the
molecules increase. This leads to an increase in the boiling temperature. Hence
the molecules can be separated in fractions (molecules of similar size) according
to the temperature at which they liquefy.
i
17
a
b
c
Apart from salicylic acid (2-hydroxybenzoic acid), what other reagent is needed?
Write a balanced equation for the reaction. You may use either structural or
molecular formulas.
Salicylic acid and acetylsalicylic acid are both white crystalline solids. The
student collected and purified the product of the reaction before sending it off for
analysis by proton NMR spectroscopy. How would the spectrum produced by this
technique allow the student to identify whether or not any acetylsalicylic acid had
been formed in the reaction?
A sample of the product was also sent off for analysis by mass spectroscopy. In
the spectrum returned there was a peak at m/e = 138 and a peak at m/e = 180.
What does this tell you about the sample?
A23.
a
b
c
d
Ethanoic anhydride
18
Traditional medicine used infusions of willow bark to help reduce pain and fever.
Analysis has shown that the infusion contains the substance salicin. It is now known
that digestive enzymes are able to convert salicin into salicylic acid.
A student proposes to synthesise a soluble form of aspirin from salicin via the reaction
pathway shown below.
a
b
i
ii
Circle the part of this molecular structure that would not contribute to its
pharmaceutical activity.
Acetylsalicylic acid is hydrolysed to salicylic acid in the body. Explain why
it is preferable to take acetylsalicylic acid rather than salicylic acid.
19
ii
Acetylsalicylic acid does not have the acidic properties or unpleasant taste of
salicylic acid so can be taken much more easily and is much less irritating to
the stomach. It does not hydrolyse back to salicylic acid until it reaches the
small intestine.
Q25.
20
10.0
= 0.07246 mol
138.0
10.0
n(ethanoic anhydride) =
= 0.09804 mol
102.0
From the equation, 2 mol salicylic acid reacts with 1 mol ethanoic anhydride.
Hence, 0.07246 mol salicylic acid reacts with 0.07246 mol ethanoic
anhydride
= 0.03623 mol ethanoic anhydride
As there is 0.09804 mol ethanoic anhydride available, salicylic acid is the
limiting reagent.
From the equation, 2 mol salicylic acid forms 2 mol acetylsalicylic acid.
Hence, 0.07246 mol salicylic acid forms 0.07246 mol acetylsalicylic acid.
M(C9H8O4) = 180.0 g mol1
Maximum mass of acetylsalicylic acid = 0.07246 180.0
= 13.0 g (three significant figures)
Aspirin is preferred to salicylic acid as it does not have an unpleasant taste and
does not irritate the lining of the mouth and stomach.
However, aspirin should not be given to children or adolescents suffering viral
infections such as influenza or chickenpox as they can develop Reyes Syndrome
(can be fatal). Also people who are taking prescribed amounts of aspirin as part of
their treatment for other conditions should not take additional aspirin to
counteract pain or fever. They should consult a pharmacist who will advise on
appropriate action.
n(salicylic acid) =
Q26.
a
b
c
21
ii
iii
i propan-1-ol
ii butanoic acid
iii ethylbutanoate
Q27.
22
Q28.
a
b
c
d
e
f
A28.
a
b
23
24
a
b
A29.
a
Cysteine is an amino acid that forms part of the polypeptide chain in albumin, a
protein that occurs in eggs. The Z-group of cysteine has the structure CH2SH.
a Draw the structure of the amino acid cysteine.
b On your diagram, label and name the two functional groups that are common to
all amino acids.
c Draw the structure of cysteine at low pH.
d Draw the structure of the two possible dipeptides that can form when a molecule
of cysteine reacts with a molecule of alanine (alanine has a Z-group of CH3).
A30.
a, b
NH3CH(CH2SH)COOH
25
Q31.
ii
26
glycine
serine
Name the functional group that has been produced as a result of:
i the reaction between glucose and fructose
ii the reaction between glycerol and palmitic acid
iii the reaction between glycine and serine
A31.
a
ii
iii
i glycoside link
ii ester link
iii peptide bond
27
Compound X contains hydrogen, carbon and oxygen. 4.50 g of X was burnt in excess
air. 2.70 g of water was produced. 3.67 L of carbon dioxide measured at 25C and
1.00 atm pressure was also produced.
a Determine the percentage composition of the compound.
b What is the empirical formula of the compound?
c The mass spectrum of compound X is shown below. Deduce the molecular
formula of X.
Mass spectrum of X.
d
e
IR spectrum of X.
28
Explain why there are only two peaks in the 1H NMR spectrum of compound X
shown below.
Identify compound X.
A32.
a
2 2.70
= 0.3mol
18
m(H) = 0.3 1 = 0.3 g
0.3 100
%(H)=
= 6.67%
4.50
pV
1 101.3 3.67
n(C) =
=
= 0.15 mol
RT
8.31 298
0.15 12 100
%C =
= 40.0%
4.50
%O = 100 (%H + %C) = 100 (6.67 + 40.0) = 53.33%
C
: H
: O
% 40.0 : 6.67 : 53.33
40.0
6.67
53.33
n
:
:
12
1.0
16
3.33 : 6.67 : 3.33
empirical formula = CH2O
From the mass spectrum, the molecular ion has a m/e of 60, i.e. molecular mass
is 60.
The molar mass of CH2O unit is 30. There must be two CH2O units in the
molecule. The molecular formula is C2H4O2.
n(H) =
29
f
g
carboxylic acid functional group. Since this absorption is not present, the
compound is not ethanoic acid.
The two peaks represent two different hydrogen environments. The peak at
chemical shift 8 is due to HCOO hydrogen and the peak at chemical shift of 3.7
is due to the three hydrogens in OCH3.
methyl methanoate
Q33.
The DNA profiles below were used as evidence in two separate court cases in which
women (M) claimed particular men (F) were the fathers of their children (C).
a
b
What do you think should have been the verdict in each case?
Each band in these profiles represents a repeating base sequence region. Why are
multiple repeating base sequence regions compared in DNA profiling?
A33.
a
The DNA profile of the child in case 1 has a number of bands in common with
that of the male. In this case, the male would be the father. In case 2, there are no
common bands in the DNA profile of the child and the male. The male is not the
childs father.
The number of repeating base sequences in the non coding region of DNA vary
between individual. In DNA profiling, the base sequences at 10 or more locations
on the chromosomes are compared. Each individual (except identical twins) will
have their own unique DNA profile.
30