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IB Chemistry SL

Topic13: Human Biochemistry Option B – Questions

1. Polypeptides and proteins are formed by the condensation reactions of amino acids.

(a) Give the general structural formula of a 2-amino acid.

(1)

(b) Give the structural formula of the dipeptide formed by the reaction of alanine and glycine.

State the other substance formed during this reaction.

…………………………………………………………………………………………
(2)

(c) State two functions of proteins in the body.

…………………………………………………………………………………………..

…………………………………………………………………………………………..
(2)
(Total 5 marks)

2. Electrophoresis can be used to identify the amino acids present in a given protein.
The protein must first be hydrolyzed.

(i) State the reagent and conditions needed to hydrolyze the protein, and identify the bond
that is broken during hydrolysis.

…………………………………………………………………………………………..

…………………………………………………………………………………………..

…………………………………………………………………………………………..
(4)

(ii) Explain how the amino acids could be identified using electrophoresis.

…………………………………………………………………………………………..

…………………………………………………………………………………………..

…………………………………………………………………………………………..

…………………………………………………………………………………………..

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(4)
(Total 8 marks)

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3. (a) Draw the straight chain structure of glucose.

(1)

(b) The structure of α-glucose is shown below.


6 CH 2 OH

5 C O
H H
4 C H 1 C
OH H
HO OH
3
C 2
C

H OH

Outline the structural difference between α-glucose and β-glucose.

......................................................................................................................................

......................................................................................................................................
(1)

(c) Glucose molecules can condense to form starch which can exist in two forms, amylose
and amylopectin. Describe the structural differences between the two forms.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

(d) 1.00 g of sucrose, C12H22O11, was completely combusted in a food calorimeter. The heat
evolved was equivalent to increasing the temperature of 631 g of water from 18.36°C to
24.58 °C. Calculate the calorific value of sucrose (in kJ mol–1) given the specific heat
capacity of water in Table 2 of the Data Booklet.

......................................................................................................................................

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(3)
(Total 7 marks)

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4. (a) The structures of three important vitamins are shown in Table 22 of the Data Booklet.
State the name of each one and deduce whether each is water-soluble or fat-soluble,
explaining your choices by reference to their structures.

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(5)

(b) Identify the metal ion needed for the maintenance of healthy bones and state the name of
the vitamin needed for its uptake.

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.....................................................................................................................................
(2)

(c) State the name of the vitamin responsible for maintaining healthy eyesight and the name
of the functional group which is most common in this vitamin.

.....................................................................................................................................

.....................................................................................................................................
(2)

(d) Identify one major function of vitamin C in the human body and state the name of the
most common disease caused by deficiency of this vitamin.

.....................................................................................................................................

.....................................................................................................................................
(2)

(e) Fresh fruits and vegetables are good sources of vitamin C. Explain why some meals made
from these foods may contain little vitamin C.

.....................................................................................................................................

.....................................................................................................................................

.....................................................................................................................................
(2)
(Total 13 marks)

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5. The structures of two sex hormones, progesterone and testosterone, are shown in Table 22 of the
Data Booklet.

(a) State the names of two functional groups that are present in both hormones.

.....................................................................................................................................

.....................................................................................................................................
(2)

(b) Identify which of the two hormones is the female sex hormone and where in the human
body it is produced.

.....................................................................................................................................

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.....................................................................................................................................
(2)

(c) Outline the mode of action of oral contraceptives.

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(3)
(Total 7 marks)

6. By referring to Table 22 of the Data Booklet, identify one vitamin that is water soluble and one
vitamin that is fat soluble. Explain the differences in solubility in terms of their structures and
intermolecular forces.

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(Total 4 marks)

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7. Discuss two benefits of using genetically modified foods.

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...............................................................................................................................................

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(Total 2 marks)

8. The structure of lactose, a disaccharide formed from glucose and galactose, is shown in the Data
Booklet. Draw the ring structure of galactose and state whether it is an  or  isomer.
(Total 2 marks)

9. (a) The general formula for saturated fatty acids is CnC2nO2. The molecular formula of
linoleic acid is C18H32O2.

(i) Determine the number of carbon to carbon double bonds in linoleic acid.

........................................................................................................................

........................................................................................................................
(1)

(ii) Iodine number is defined as the number of grams of iodine that adds to 100 g of a
fat or an oil in an addition reaction. Determine the iodine number of linoleic acid.

........................................................................................................................

........................................................................................................................

........................................................................................................................
(2)

(b) (i) State one structural similarity between fats and oils.

........................................................................................................................

........................................................................................................................
(1)

(ii) Explain, by referring to their structures, why fats are solid at room temperature, but
oils are liquid.

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(3)
(Total 7 marks)

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10. (a) State the name of a disease which results from the deficiency of each of the following
vitamins.

vitamin A .................................................................................................................

vitamin B .................................................................................................................

vitamin C .................................................................................................................
(2)

(b) A person consumes an excess of both vitamin A and C. State, with a reason, which one is
more likely to be stored in the body and which is more likely to be excreted.

...................................................................................................................................

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...................................................................................................................................

...................................................................................................................................
(2)
(Total 4 marks)

11. Identify three types of interactions responsible for the tertiary structure of proteins.

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(Total 2 marks)

12. The structures of vitamins A and C are shown in Table 22 of the Data Booklet. State, with a
reason, whether each is fat soluble or water soluble.

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(Total 3 marks)

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13. (a) (i) Deduce the structure of one of the dipeptides that can be formed when the two
aminoacids below react together.

O O

H2N CH C OH H2N CH C OH

CH CH3
CH3 CH 3

(2)

(ii) State the name given to this type of reaction and identify the other product of the
reaction.

.........................................................................................................................

.........................................................................................................................
(2)

(b) Describe how a mixture of aminoacids can be analysed using electrophoresis.

...................................................................................................................................

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(4)

(c) (i) Explain what is meant by the primary structure of proteins.

.........................................................................................................................

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(1)

(ii) Explain, with reference to hydrogen bonding, why the -helix and -sheet
secondary structures of proteins are different.

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(2)
(Total 11 marks)

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14. (a) The equilibria, which exist in an aqueous solution of glycine, are shown in the structures
below.

H2N CH2  COO H3N+ CH2 COO H3N+ CH2 COOH


A B C

State which of the forms A, B or C occurs in the greatest concentration at:

low pH: ...............................

high pH: ..............................


(2)

(b) A mixture of amino acids with different isoelectric points can be separated using
electrophoresis.

(i) Outline the essential features of electrophoresis.

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(3)

(ii) Arginine, glutamic acid and glycine undergo electrophoresis at pH 6.0. Using table
20 of the Data Booklet identify the amino acid that moves towards:

the positive electrode: .....................................................................................

the negative electrode: ....................................................................................


(2)
(Total 7 marks)

15. Iodine number is defined as the number of grams of iodine that reacts with 100 g of a
triglyceride in an addition reaction. The iodine number of palmitic acid (Mr = 256) is 0 and
linolenic acid (Mr = 278) is 274.

Determine the number of double bonds in linolenic acid, showing your working.

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(Total 3 marks)

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16. The structures of two synthetic hormones are shown below:

OH OH
CH3 CH3
CH3 C C H
CH3

O O

A B

Hormone A is similar in structure to testosterone and hormone B is similar in structure to


progesterone.

(a) Explain why hormone A is prescribed to some patients.

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....................................................................................................................................
(2)

(b) Suggest why hormone A is banned for participants in major sporting events.

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(1)

(c) Describe how hormone B functions as an oral contraceptive.

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(2)
(Total 5 marks)

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17. The structures of the amino acids glycine and serine are shown in Table 20 of the Data Booklet.

(i) Draw the structure of one of the dipeptides formed when one molecule of glycine and one
molecule of serine react together. Show all the bonds in the link between the two
molecules.

(2)

(ii) State the type of reaction occurring and identify the other product of the reaction.

....................................................................................................................................

....................................................................................................................................
(1)
(Total 3 marks)

18. State the general role of hormones in the body and identify the gland that controls their
production.

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(Total 2 marks)

19. The structures of the amino acids glycine and serine are shown in Table 20 of the Data Booklet.
Draw the structure of one of the dipeptides formed when one molecule of glycine and one
molecule of serine react together. Show all the bonds in the link between the two molecules.
(Total 2 marks)

20. The structure of a protein can be analysed using paper chromatography.

(i) Describe the process that the protein must undergo before chromatography is used and
explain why it is necessary.

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....................................................................................................................................
(2)

(ii) Explain how paper chromatography is used to identify the individual amino acids.

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(4)
(Total 6 marks)

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21. Fats and oils are formed when fatty acids react with glycerol.

(a) Outline two structural differences between saturated and unsaturated fats.

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(2)

(b) Explain why saturated fats have higher melting points than unsaturated fats with similar
relative molecular masses.

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(2)
(Total 4 marks)

22. The structures of some hormones are shown in Table 22 of the Data Booklet.

(a) Identify one hormone with a steroid backbone, state where it is produced and outline its
specific role in the body.

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(2)

(b) Identify one hormone with a non-steroid backbone, state where it is produced and outline
its specific role in the body.

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(2)
(Total 4 marks)

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23. The structure of sucrose is shown in Table 22 of the Data Booklet.

(a) State the name of the oxygen-containing link between the two rings in the structure.

....................................................................................................................................
(1)

(b) Deduce the ring structures of the two monosaccharides that condense to form a molecule
of sucrose.
(2)

(c) Identify the other product formed during this condensation reaction.

....................................................................................................................................
(1)

(d) State the empirical formula of a monosaccharide.

....................................................................................................................................
(1)
(Total 5 marks)

24. The structures of three vitamins are shown in Table 22 of the Data Booklet.

(a) Predict which of the three vitamins is most soluble in water, giving a reason for your
choice.

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....................................................................................................................................
(2)

(b) Name two functional groups present in all three vitamins.

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(1)

(c) State the function of vitamin D in the human body and describe one effect of vitamin D
deficiency.

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....................................................................................................................................
(2)
(Total 5 marks)

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25. The structure of sucrose is shown in Table 22 of the Data Booklet.

(a) State the name of the oxygen-containing link between the two rings in the structure.

....................................................................................................................................
(1)

(b) Deduce the ring structures of the two monosaccharides that condense to form a molecule
of sucrose.

(2)

(c) State the empirical formula of a monosaccharide.

....................................................................................................................................

....................................................................................................................................
(1)
(Total 4 marks)

26. The structures of three vitamins are shown in Table 22 of the Data Booklet.

(a) Predict which of the three vitamins is most soluble in water, giving a reason for your
choice.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
(2)

(b) State which two vitamins can be classified as primary alcohols.

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....................................................................................................................................
(1)

(c) State the function of vitamin D in the human body and describe one effect of vitamin D
deficiency.

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(2)
(Total 5 marks)

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27. When many 2-amino acid molecules react together a protein is formed. These proteins have
primary, secondary and tertiary structures.

(a) State the type of intermolecular force responsible for maintaining the secondary structure.

.....................................................................................................................................
(1)

(b) Describe two other ways in which the tertiary structure of the protein is maintained.

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(2)
(Total 3 marks)

28. (a) For each of the following vitamins describe its function in a diet and one effect of its
deficiency.

Vitamin C ...................................................................................................................

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Vitamin D ...................................................................................................................

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(4)

(b) Discuss two solutions for the prevention of nutrient deficiencies.

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(2)
(Total 6 marks)

29. (a) State what is meant by dietary fibre.

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(2)

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(b) Give two examples of dietary fibre.

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.....................................................................................................................................
(2)

(c) Describe two reasons for the inclusion of dietary fibre in a healthy diet.

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(2)
(Total 6 marks)
30. (a) Compare the structural properties of starch and cellulose.

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(4)

(b) Explain why humans cannot digest cellulose.

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(1)
(Total 5 marks)

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IB Chemistry SL
Topic13: Human Biochemistry Option B – Answers

1. (a) RCH(NH2)COOH; 1

(b) H2NCH(CH3)CONHCH2COOH / H2NCH2CONHCH(CH3)COOH


water/H2O; 2

(c) structure/catalysis or enzymes/energy source/oxygen transport; 2


Any two, [1] each. Accept specific structures, e.g. hair, muscle.
[5]

2. (i) acid/hydrochloric acid/HCl (accept H2SO4)


Accept base/NaOH.
concentrated/heat or high temperature or boil/
time (any two, [1] each);

O
C N / C N / peptide / amide;
H 4

(ii) mixture/amino acids spotted on paper/gel;


apply voltage;
develop/ninhydrin/organic dye;
measure distances moved/compare with known samples/measure isoelectric
points and compare with data; 4
Marks may be given for a suitable diagram.
[8]

3. (a)

H H OH H
HOH 2 C C C C C CHO
OH OH H OH 1
No penalty for “sticks” or for OH groups written back-to-front,
eg. OH- instead of HO-.
(b) the –OH group on the first carbon atom is inverted in β-glucose 1
(c) one (amylose) is a straight chain polymer whereas the other (amylopectin)
is branched; one (amylose) has only 1,4 bonds (between the monomers)
whereas the other (amylopectin) has 1,4 and 1,6 bonds; 2
(d) Mr for sucrose =342;
heat evolved = 0.631(kg)×4.18 (kJ kg–1K–1 )×6.22(K) = 16.4 kJ;

calorific value = 16.4  342 = 5.61×103 kJ mol–1; 3


1.00
Allow answers in range 5610 to 5620.
Penalize for more than 5 sig. figs.
ECF from incorrect Mr.
[7]

16
4. (a) vitamin A
retinol is fat-soluble;
vitamin C
ascorbic acid is water-soluble;
vitamin D
calciferol is fat-soluble;
fat-soluble because mainly composed of hydrocarbon chain/non
polar groups;
water-soluble because of presence of several/many hydroxyl/
OH/polar groups; 5
(b) Ca2+/calcium;
vitamin D/calciferol; 2
(c) vitamin A/retinol;
alkene; 2
(d) helps to form collagen/connective tissue/acts as antioxidant; 2
scurvy/scorbutus;
(e) dissolves in water;
oxidized/destroyed by heating/boiling; 2
[13]

5. (a) carbonyl/ketone
Accept alkanone but not aldehyde.
alkene; 2
(b) progesterone;
ovaries; 2
(c) change release of hormones/FHS/LH (from hypothalamus/pituitary gland);
prevent ovulation/egg release; prevent attachment of egg to uterus;
prevent sperm from reaching egg; 3
Award [1] each for any three.
[7]
6. vitamin C is water soluble and vitamin A/D is fat soluble;
vitamin C has 4/several OH groups/vitamin A/D has only 1/fewer
OH groups;
vitamin A/D has large non-polar/hydrocarbon part/chain/ring;
vitamin C has hydrogen bonding and vitamin A/D has van der Waals’ forces; 4

[4]
7. Benefits
improve food productivity/provide more food;
(food) crops are more resistant to disease/more resistant to insect attack
/more tolerant to toxins;
improve aesthetics/composition of some foods;
improved flavour;
improved texture;
improved nutritional value;
improved shelf life;
incorporation of anti-cancer substances/vaccines/reduce exposure to
less healthy fats; 2 max
Award [1] each for any two.
[2]

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8.

CH 2OH

O
OH OH
H
OH H ;

H H

H OH
β isomer;
[2]

9. (a) (i) 2 double bonds; 1

(ii) 280.5 g linoleic acid adds to 507.6 g I2;

507.6 100
100 g adds to  181; 2
280.5
Allow ECF from (i).
Do not penalize for use of whole number atomic masses.

(b) (i) both are esters/tri-glycerides/tri-esters; 1

(ii) Fats Oil


saturated/no C=C bonds or unsaturated/1 or more
C=C bonds;
(saturated) chains pack closely or (unsaturated) chains pack less
closely;
van der Waals’ forces are stronger or van der Waals’ forces are weaker; 3
Accept intermolecular forces for van der Waals’ forces.
[7]

10. (a) vitamin A


night blindness/xerophthalmia;

vitamin C
scurvy/scorbutus;

vitamin D
rickets; 2
Award [2] for 3 correct, [1] for 2 correct.

(b) vitamin A
is stored (in the body) because it is fat-soluble;

vitamin C
is excreted because it is water-soluble; 2
[4]

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11. hydrogen bonding;
disulphide links/bonds/bridges;
van der Waals’ forces;
ionic/ion-dipole/dipole-dipole;
Award [2] for any three.
Award [1] for any two.
[2]

12. A is fat soluble and C is water soluble;


A has only one OH group/A is mostly hydrocarbon;
C has many OH groups which can form hydrogen bonds with water;
Do not penalise if OH is stated with a minus sign.
[3]

13. (a) (i) 2

O H O H O
O
H2N CH C N CH C H2N CH C N CH C OH
OH
CH CH3 CH3 CH
CH3 CH3 CH3 CH3

Award [1] for the correct peptide bond and an additional [1] if
the rest of the structure is correct.
O H O

Accept C N or C NH for the peptide bond.

(ii) condensation;
H2O/water; 2

(b) mixture placed on gel/paper;


use of buffer solution;
potential difference applied;
amino acids move differently (depending on pH/isoelectric point);
develop/spray with ninhydrin;
compare distances travelled with standards (OWTTE)/compare the
isoelectric points; 4
Award [1] each for any four.

(c) (i) sequence/chain of amino acids; 1

(ii)  - helix = intramolecular/spiral/OWTTE;


 - sheet = attraction between chains (accept intermolecular)/OWTTE; 2
Accept suitable diagrams.
[11]

14. (a) low pH


C;
high pH
A; 2

19
(b) (i) place sample on gel;
with (buffer) solution of known pH;
apply voltage/potential difference;
Do not accept current applied.
develop/spray with ninhydrin;
measure distance moved/compare with known iso-electric point/
compare with standards; 3
Award [1] each for any three.

(ii) positive electrode


glutamic acid;
negative electrode
arginine; 2
[7]

15. 761.7 g of I2/274÷253.8 = 1.08 mol;


3 mol of I2/6 mol of I atoms/100÷278 = 0.360 mol;
(1.08÷0.360 = ) 3 double bonds;
Some correct working must be shown.
Allow ECF if Mr of iodine used as 126.9 instead of 253.8.
Accept correct alternative methods.
[3]

16. (a) recovery from injury/surgery/starvation/illness/disease;


increased rate of protein synthesis/tissue/muscle building/increase in
muscle mass; 2

(b) enhances performance/strength unfairly; 1

(c) mimics the action of progesterone in pregnancy;


prevents release of the egg/no ovulation;
prevents release of FSH and LH by the pituitary gland; 2
Award [1] each for any two.
[5]

17. (i) 2

H 2N CH 2 C N CH COOH

O H CH 2 OH

OR
O H

H 2N CH C N CH 2 COOH

CH 2 OH

If peptide bond abbreviated, eg CONH but structure


otherwise correct, award [1].

(ii) condensation and water/H2O; 1


[3]

20
18. chemical messengers;
pituitary (gland)/hypothalamus;
[2]

19.

H2N CH 2 C N CH COOH

O H CH 2OH

O H

H 2N CH C N CH 2 COOH

CH 2OH
OR
Award [1] for peptide bonds correctly shown in full and a
further [1] if rest of structure correct.
If peptide bond abbreviated, eg CONH but structure
otherwise correct, award [1].
[2]

20. (i) (warm with dilute) hydrochloric acid; to hydrolyse protein/to break it down
into amino acids/to break the peptide bonds; 2

(ii) (mixture of) amino acids spotted on paper (and known amino acids spotted
on paper);
water/solvent/eluent flows up/down paper;
amino acids separate because they have different solubilities in water/
solvent/eluent and/or different adsorption on paper;
amino acid positions identified/sprayed with ninhydrin/locating agent;
locations compared with known amino acids/Rf values compared; 4
[6]

21. (a) saturated have only single carbon to carbon/CC bonds/unsaturated have
double carbon to carbon/C=C bonds;
Do not award mark if no reference to carbon-carbon bonds.
saturated have a straight hydrocarbon chain/unsaturated have a kinked
hydrocarbon chain/OWTTE; 2
Accept bond angle of 109(.5) in saturated and 120 in
unsaturated.

(b) chains pack closer together;


stronger intermolecular forces/van der Waals' forces; 2
Accept London forces and dispersion forces in place of van der
Waals' forces.
Do not accept stronger hydrogen bonding.
Award [0] if any reference to breaking carbon-carbon bonds.
[4]

21
22. (a) (testosterone)
testes;
development of male sex organs/characteristics/tissue/muscle/bone
growth/anabolic effect;

OR

(oestradiol)
ovaries;
ovulation/development of female sexual characteristics;

OR

(progesterone)
ovaries;
prepares uterus for fertilized egg; 2

(b) (adrenaline/epinephrine)
adrenal glands;
regulates body's preparation for stress/OWTTE;

OR

(thyroxine)
thyroid gland;
regulates body's metabolism;

OR
(Insulin)
pancreas/Islets of Langerhans;
Regulation of glucose concentration in bloodstream/regulates blood
sugar levels; 2
[4]

23. (a) glycosidic/glucoside/ether; 1

(b)

CH 2 OH
HOH 2 C O H
O
H H
HH ; ;
H HO
OH H
HO CH 2 OH
HO OH

H OH OH H

2
Do not penalize candidates who draw bonds connected to
incorrect atoms e.g. HO instead of OH.

(c) water/H2O; 1

(d) CH2O; 1
[5]

22
24. (a) vitamin C/ascorbic acid;
four/many OH groups/small proportion of hydrocarbon/can form hydrogen
bonds with water/OWTTE; 2

(b) alkene and hydroxyl/alcohol; 1

(c) needed for uptake of calcium/phosphate;


bone problem such as softening/weakness/malformation/rickets; 2
[5]

25. (a) glycosidic/glucoside/ether; 1

(b)

CH 2 OH
HOH 2 C O H
O
H H
HH ; ;
H HO
OH H
HO CH 2 OH
HO OH

H OH OH H

2
Do not penalize candidates who draw bonds connected to the
incorrect atom  e.g. HO instead of OH

(c) CH2O; 1
[4]

26. (a) vitamin C/ascorbic acid;


four/many OH groups/small proportion of hydrocarbon/can form hydrogen
bonds with water/OWTTE; 2

(b) vitamins A/retinol and C/ascorbic acid; 1

(c) needed for uptake of calcium/phosphate; bone problem such as


softening/weakness/malformation/rickets; 2
[5]

27. (a) hydrogen bonding; 1

(b) van der Waals’ forces/hydrophobic interactions/London/dispersion forces;


ionic bonding/(formation of) salt bridges/electrostatic attractions;
covalent bonding/(formation of) disulfide bridges; 2
max
Award [1] each for any two.
Do not accept sulfur bridges or hydrogen bonding.
[3]

28. (a) vitamin C function


collagen formation/production of connective tissue/enhances
absorption of iron (from food)/helps healing of wounds/can prevent
bacterial infection/antioxidant/bone or teeth formation;
effects of deficiency

23
scorbutus/scurvy;
vitamin D function
uptake of calcium/phosphorus/bone or teeth formation;
effects of deficiency
rickets; 4

(b) Any two of the following:


providing food rations that are composed of fresh and vitamin-
and mineral-rich foods;
adding nutrients missing in commonly consumed foods;
genetic modification of foods;
providing nutritional supplements; 2
max
[6]

29. (a) plant material that is not hydrolysed by enzymes (secreted by the human
digestive tract);
may be digested by microflora in the gut; 2

(b) Any two of the following:


cellulose;
hemicellulose;
lignin;
pectin; 2
max

(c) (may be helpful in the prevention of conditions/health problems such as)


Any two of the following:
diverticulosis;
irritable bowel syndrome;
constipation;
obesity;
Crohn’s disease;
haemorrhoids;
diabetes mellitus; 2
max
[6]
30. (a) both are polymers of glucose;
starch has two forms: amylose a straight chain polymer with  – 1, 4 linkages;
and amylopectin a branched polymer with  – 1, 4 and  – 1, 6 linkages;
cellulose has  – 1, 4 linkages; 4

(b) absence of cellulase enzyme; 1


[5]

24

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