IB Chemistry HL Option F Food Chemistry

May 2009
1. Artificial food colourants have recently been linked to increased
hyperactivity in children. Many foods are colourful because of the natural
pigments they contain.
a. Explain why naturally-occurring pigments are coloured.
[1]
b. State the class of pigments that give cranberries and strawberries
their colour. [1]
c. i. State the class of pigments that give carrots and tomatoes their
colour.
[1]
ii. Outline why this class of pigment is susceptible to oxidation, and
the effect of oxidation on this pigment.
[2]
2. Antioxidants occur naturally and are often added to extend the shelf life
of our food.
a. Define the term antioxidant.
[1]
b. Explain the differences between the three main types of antioxidant.
Include in your answer:
An example of each type of antioxidant
A brief account of how it works.
[6]
c. Table 22 in the Data Booklet shows the structures of some antioxidants.
Determine the two functional groups that are found in all of these
synthetic antioxidants:
2-tert-butyl-4-hydroxyanisole (2-BHA), 3-tert-butyl-4-hydroxyanisole (3BHA) and 3,5-di-tert-butyl-4-hydroxytoluene (BHT).
[2]
d. Describe the step by step mechanism for the free radical reaction that
causes an oily fish such as mackerel to become rancid. Include the
name of each step and an equation for each step in your answer.
[6]
Step 1:
Step 2:
Step 3:
3. Genetically modified (GM) foods are now widely available, although in
some countries environmental groups are campaigning against them.
Define the term genetically modified food and discuss the benefits and
concerns of using GM foods.
[5]
May 2010
1. Simple sugars are nutrients and are also described as monosaccharides.
a. Distinguish between a food and a nutrient.
[2]

b. State three characteristic features of all monosaccharide molecules.

[3]
c. Explain the chemistry behind the non-enzymatic browning reaction
that occurs when making fudge from sugar and cream.
[3]
2.
a. Explain why pigments such as anthocyanins are coloured.
[2]
b. The wavelength of visible light lies between 400 and 750 nm. The
absorption spectrum of a particular anthocyanin is shown below.

i.

Explain what effect, if any, the absorption at 375 nm will have on

the colour of the anthocyanin.
[1]
ii.
Explain what effect, if any, the absorption at 530 nm will have on
the colour of the anthocyanin.
[1]
c. List two factors which could alter the precise colour of a particular
anthocyanin.[2]
3. The structure of vitamin C is given below.

a. Refer to the structure to explain why vitamin C can exist in a +(d) form
and a (l) form and explain the difference between the two forms.
[2]
b. The amino acid alanine is optically active. One of its enantiomers
(labeled A) is represented below.

i.
ii.

In the space above draw the other enantiomer of alanine (labeled

B). [1]
Explain which of the two enantiomers (A or B) is the D isomer.
[3]

4.
a. During oxidative rancidity hydroperoxides are formed. These degrade
to produce volatile aldehydes and ketones which produce the
unpleasant smells associated with food that has gone off. One way of
prolonging the shelf life of food is to add the antioxidant BHT.

i.

Describe two structural features of BHT which are responsible for its
antioxidant properties.
[2]
ii.
Explain how BHT can prolong the shelf life of food.
[1]
b. Another antioxidant is vitamin C. This works in a different way to BHT.
Outline how vitamin C functions as an antioxidant.
[2]
May 2011
1.
a. Rancidity is the perception of flavours in lipids that our senses perceive
as off because of a disagreeable smell, taste, texture or appearance.
The processes that create the off flavours may be hydrolytic rancidity
or oxidative rancidity in lipids.
i. Predict the products of hydrolytic rancidity of fats.
[2]
ii.
The hydrolysis of milk products is used in the making of cheese.
State two conditions which increase the rate of hydrolysis of fats in
milk.
[2]

iii.

Potato chips are cooked in oils made from unsaturated fatty acids.
Explain in terms of chemical processes why potato chips are
purchased in sealed, opaque, nitrogen filled foil packs and taste
best when freshly opened.
[3]
b. Initiation, propagation and termination steps occur in the free-radical
chain mechanism during oxidative rancidity. For each step, state one
related
equation.
[3]
2.
a. Antioxidants are substances that slow the rate of oxidation of foods and
may also be consumed to provide health benefits. Two traditional foods
with antioxidant properties are green tea and oregano. Green tea
contains epigallocatechin-3-gallate (EGCG) and oregano contains
rosmarinic acid. The structures of these two compounds are shown
below.

i. Explain why both EGCG and rosmarinic acid have antioxidant

properties.
[1]
ii. List two health benefits of consuming foods such as green tea and
oregano.[2]
b. Anthocyanins are naturally occurring pigments responsible for the
colour of blueberries and cranberries. The structures of two forms of
anthocyanins are show in Table 22 of the Data Booklet.
i. Using the abbreviations QB for quinoidal base and FC+ for flavylium
cation, state an equation to describe how pH affects the colour of
anthocyanins.
[1]
ii. Suggest why blueberries should not be stored in aluminum cans.
[2]
c. Compare the structures of the natural pigments, chlorophyll and heme
B using Table 22 of the Data Booklet.
[4]
3. Carvone is a member of a family of compounds called terpenoids.
Carvone occurs in two enantiomeric forms. (S)-(+)-carvone is the principal
component of caraway seed oil and (R)-()-carvone is the principal
component of spearmint oil.

a. Identify the chiral centre in carvone, with an asterisk, *.

[1]

b. Explain the meaning of the R and S notation and how this differs from
the d and l notation.
[2]
c. The structure represented is (S)-(+)-carvone. Explain how this has been
deduced.
[2]
May 2012
1. Most foods are complex mixtures and many components of them are
nutrients.
a. State an example of a food that is not a nutrient and use this to explain
the difference between these two terms.
[3]
b. Anthocyanins, carotenes and porphyrins are coloured substances found
in foods. Their structures are shown in Table 22 of the Data Booklet.
i. Identify the common feature in their structures that results in these
compounds all being coloured and explain this on a molecular level.
[3]
ii. Under certain conditions, anthocyanins are converted into a
colourless carbinol pseudobase, an example of which is shown
below.

In terms of its structure, explain why the pseudobase is colourless

even though the anthocyanin is coloured.
[1]
c. The absorption spectrum of -carotene is shown below.

In this spectrum, explain why carotenes have their typical colour.

[2]
d. There are distinct differences between the solubilities of anthocyanins
and carotenes. Describe these and explain the differences in terms of
their
structures.
[3]
2. Rancidity limits the shelf life of foods containing oils and fats.
a. Rancidity can occur as a result of two separate processes. State these
processes and explain the difference between them.
[3]
b. Substances such as THBP (2,4,5-trihydroxybutyrophenone) and TBHQ
(tert-butylhydroquinone) are often added to slow down rancidity.
Explain how additives such as THBP and TBHQ delay rancidity.
[2]
c. State the name of one naturally occurring substance which has a
similar effect in slowing down rancidity. Identify a food that is rich in
this and state an additional health benefit thought to arise from its
regular consumption.
[3]
Compound:
Food:
Benefit:
3. Texture is an important feature of food. Various dispersed systems have
distinctive textures.
a. Describe what is meant by the term dispersed system.
[1]
b. Identify the phases of the two components of an emulsion.
[1]
c. Emulsifiers such as lecithin are frequently used to prevent the
separation of emulsions. One compound of lecithin has the structure
shown below.

Explain how emulsifiers, such as this, stabilize emulsions.

[3]
May 2013
1. Antioxidants occur naturally (such as vitamin C) or can be synthetic.
a. Define the term antioxidant.
[1]

b.
i. Identify an element that is a common naturally occurring
antioxidant.
[1]
ii. State one food in which this antioxidant can occur.
[1]
c. The structures of three synthetic antioxidants, 2-BHA, 3-BHA and BHT
are given in Table 22 of the Data Booklet. Another synthetic antioxidant
is THBP whose structure is shown below.

i. Deduce which of these four antioxidants contain the phenol group.

[2]
ii. Deduce whether THBP contains the tertiary butyl group or not.
[1]
iii. Suggest the function of the tertiary butyl group in antioxidants.
[1]
2. The food industry uses food-grade dyes and pigments to increase the
appeal of food products.
a. State the difference in terms of solubility between a dye and a pigment.
[1]
b. The pigment associated with the olive-green colour of the outer shell of
the American lobster is astaxanthin, shown below. When cooked the
lobster changes to a red colour.

i. Identify the class of pigment to which astaxanthin belongs.

[1]
ii. Explain why the properties of pigments in the shell of a live lobster
can lead to colour variation (for example, from olive-green to
orange).
[1]
iii. Explain how the colour of astaxanthin changes to red when cooked.
[2]
3. The Maillard reaction is the basis of non-enzymatic browning and involves
the reaction between carbohydrates and proteins.
a. The first step of this reaction involves a condensation reaction between
a reducing sugar, such as glucose, and an amino acid.
i. Using RCHO to represent glucose and H2NR to represent an amino
acid, deduce the structural formula of the product.
[1]
ii. Identify the other product of this reaction.
[1]
b. Other than condensation, state the name of one type of reaction
involved in the other two steps of the Maillard reaction.
[1]
4. The structure below shows an enantiomer of -ionone, which has a
raspberry flavour.

a. Identify the chiral centre in the structure above with an asterisk (*).
[1]
b. Explain what is meant by the R, S notation and how this is different to
the +(d) and (l) notation.
[2]
c. Deduce whether the enantiomer shown is R or S and explain your
answer.
[2]
d. Another enantiomer of -ionone has a different flavour. Suggest a
reason for this difference.
[1]
e. Two other optical isomers which have an effect on flavour are +(d) and
(l) limonene. State the flavour associated with each enantiomer.
[1]
+ (d) limonene:
(l) limonene:
5. Auto-oxidation is the chemical process responsible for the rancidity of
butter.
a. Using RH as the formula for the fat in butter, state three equations
associated with the reaction of RH with oxygen, resulting in the
formation of hydroperoxides. [2]
b. In this process the hydroperoxides act as intermediates. State why they
degrade and rearrange to other compounds and identify a functional
group in these
compounds.
[1]
May 2014
1. The formula of linoleic acid is given in Table 22 of the Data Booklet.
a. Identify the structural formula of the triglyceride formed when three
molecules of linoleic acid react with one molecule of glycerol (propane1,2,3-triol),
CH2OHCHOHCH2OH.
[1]
b. State the other product formed during this reaction.
[1]

c. Explain why the triglyceride formed from linoleic acid and glycerol is a
liquid and not a solid at room temperature.
[2]
d. Describe how the triglyceride formed from linoleic acid and glycerol
could be converted into a saturated fat and give any necessary
conditions.
[2]
e. Other than the fact that it is a solid at room temperature, discuss two
advantages and two disadvantages of a saturated fat compared to
unsaturated fat or oil.
[4]
Advantages:
Disadvantages:
2. Describe how the following additives can prolong the shelf life of food:
a. sodium benzoate and benzoic acid.
[1]
b. potassium nitrite and potassium nitrate.
[1]
3. Lycopene occurs naturally in tomatoes and is responsible for their red
colour. Lycopene is a known antioxidant and some people believe that it is
effective at preventing prostate cancer. Its structure is shown below.

a.
i. Lycopene is a hydrocarbon. State the class of naturally occurring
pigments to which it belongs.
[1]
ii. Outline why lycopene is a coloured compound.
[1]
iii. The UV/VIS spectrum of lycopene is shown below.

Explain why it is coloured red.

[1]
iv. Antioxidants can be divided into three main types. Lycopene is a
reducing agent and acts as an antioxidant by removing or reducing
the concentration of oxygen. Others, such as BHT (3,5-di-tert-butyl4-hydrotoluene), inhibit the formation of free radicals or interrupt
the propagation of free radicals. Explain how the third type of
antioxidants functions and give one example.
[2]
b.
i. Describe how a fatty acid, RH, undergoes oxidative rancidity. Your
answer should state the names of the three different steps and
include one equation for each step.
[3]
ii. Explain how an antioxidant such as BHT is able to inhibit the
formation of free radicals during the oxidative rancidity of a fatty
acid.
[2]
4. Your school is holding a debate on the benefits and concerns of
genetically modified (GM) food. Several speakers have argued the
benefits of GM foods and included such factors as enhanced taste,
resistance to disease and increase in crop yields. Discuss three arguments
you would use to highlight the concerns of using GM foods.
[3]