Who took John’s iPod?

-- An organic compound mystery

John Doe is a 10th grade student at Scripps Ranch high school who works at McDonald’s after school and on the weekend.
While on break, John was studying for his biology test and listening to his new iPod (something he is not allowed to do in
class). There were seven other workers taking a break at the same time, each having something different for lunch.
Although they like their job, after watching “Supersize Me” more employees started bringing their lunch to work. John‘s
girlfriend stopped by near the end of his break, and he rushed out to see her and forgot his iPod and biology book in the
break room. When he realized, he hurried back and found only his biology book and some traces of food. His iPod was
gone! First John freaked out, but he calmed down when he realized he could use his knowledge of organic compounds to
figure out which of his coworkers left the food on his textbook and who took his iPod.

What are organic compounds?

Before solving the iPod mystery you need to remember some information about macromolecules. Almost all of the food
we eat comes from plants and animals. Plants and animals contain mainly water and organic compounds, which are
molecules made by living organisms such as plants or animals. These molecules come in diverse shapes and sizes ands
serve a variety of purposes related to cellular structure and function.

Carbohydrates

Most carbohydrates contain only carbon, oxygen, and hydrogen. The simplest forms of
carbohydrate molecules are the monosaccharides (single sugars) and they usually contain
atoms of these elements in the ratio of 1 Carbon : 2 Hydrogen : 1 Oxygen. One of the most
important monosaccharides is glucose (C6H12O6), the end product of photosynthesis in plants
and the main fuel for cellular respiration (how organisms make energy available to do
cellular work).

Carbohydrates are also found in the form of polysaccharides (many sugars), which are long chains of monosaccharides
linked together. Starch, a polysaccharide composed of only glucose monomers, is an especially abundant component of
plants. Starch is the main way plants store excess glucose created by photosynthesis. Most of the carbohydrates we eat
are derived from plants.

Animals store excess glucose from their diet as

glycogen, which is another polysaccharide.
Although starch and glycogen are both composed
of glucose subunits, the glucose molecules are
bonded together in different ways so these
polysaccharides are not identical.

Lipids

Lipids are compounds that contain mostly carbon and hydrogen.

They are grouped together solely on the basis of their insolubility in
water. The lipids we consider in this lab are fats and oils, which are
generally used as long term storage molecules in plants and animals.
You are probably familiar with the fact that the human body converts
food into fat. This fat is stored in your tissues until your food intake
is lower than your metabolic needs, at which time the fat is converted
to energy to fuel cellular work. Plants too, can store lipids. Seeds
are often surrounded by lipids that can be metabolized by the developing embryo when germination time comes in order
to provide energy for growth. Thus we obtain corn oil, peanut oil, olive oil and others by pressing seeds.

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 Proteins

The structure of a protein is determined by the amino acid subunits that

make up the molecule. Although there are only 20 different naturally
occurring amino acids, each protein has a unique sequence. The individual
amino acids are linked by strong peptide bonds, and the functional groups
that are part of each of the amino acids also interact with the functional
groups of neighboring amino acids to help shape the molecule.

What are indicators?

An indicator is a substance that changes color in the presence of a particular type of molecule. A color change typically
means a positive result and a certain molecule is present whereas no change in color usually means a given molecule is
absent. Today you will be testing the substances listed in the following table to learn about indicator test results. Predict
whether each substance is an organic compound and if so, which class. Later you will use these tests to analyze several
types of food and the evidence left at the scene of the crime to find out who left the crumbs on John’s textbook.

Table #1: Prediction Table – for controls

Substance Do you think this substance is a carbohydrate (sugar or
starch),
lipid, protein, or none of these? Pick only one per substance.
Vegetable oil
Glucose
Starch from corn or potatoes
Powdered egg whites
Water

Safety First!! All students need to follow the guidelines outlined in the safety contract signed early in the year. All
students need to wear safety goggles in class during the entire lab as long as chemicals are out. Students will be
penalized (- 10 pts.) on their lab for first offense and may receive a zero (0) if repeat offender.

Testing for Carbohydrates (Starch)

Put 10 drops of food in the correct labeled test tube. Add 10 drops of Lugol’s solution (iodine) to each test tube.
CAUTION: Lugol’s stains. In the presence of starch, iodine will change color from yellow-brown to blue-black.
Observe the contents of your test tubes and record the amount of starch present (0, +, ++, +++, ++++) in your data
chart. ++++ represents food with the most starch. Rinse glassware for next step.

Testing for Carbohydrates (Sugar)

Put 10 drops of each food in correct labeled test tube. Add 10 drops of Benedicts solution to each test tube. CAUTION:
Benedicts solution is poisonous. DO NOT put any in your mouth and do not swallow any. Using a test tube holder,
place the test tubes in a hot water bath (using large beaker to hold water). You may heat multiple tubes at the same time.
Heat 2-3 minutes. CAUTION: continue to use test tube holder to handle. Always point away from people, contents may
fly out of tube. Using the test tube holder, transfer the test tubes back to the rack. If the substance in your test tube
contains sugar, Benedicts solution will change color. Use the following guide for your data sheet: Blue = no sugar,
Blue/Green = + trace, Yellow = ++ little sugar, Orange/Red = +++ some sugar, and Deep Orange/Red = ++++ Much
sugar. (If you can’t tell color, use a white paper as a background). Record amount of sugar onto data table. Clean
glassware for next step.

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Testing for Proteins
Put 10 drops of each food in correct labeled test tube. To test for protein you will use Biuret reagent as an indicator.
Biuret reagent turns from blue to purple in the presence of protein. Add 20 drops of biuret reagent to each container. Stir
the contents of each container. Do not heat!! CAUTION: Biuret reagent contains sodium hydroxide, a strong base. Be
very careful not to splash or spill any. If you splash any reagent on yourself, wash it off immediately with water. Call
your teacher for assistance. If the substance in your test tube contains protein, Biurets will change color. Use the
following guide for your data sheet: original color (blue) = 0, light pink = +, pink = ++, purple = +++ and dark purple = +
+++. Record the color of each Biuret solution in the data table by putting a plus next to those samples testing positive for
protein and a minus/0 for those testing negative.

Testing for lipids

Put 1-2 drops of 5 food solutions on paper bag. Leave for 30 sections
Observe and compare/contrast translucence of each food substance. The food containing the most lipids should be
recorded as ++++. The greater the translucence, the more the newsprint/brown bag appears to disappear. Try putting the
bag with sample over this worksheet. If you can “see thru” bag, sample is a lipid.
Record the information in order of translucence (0, +, ++, +++, ++++) in your data chart and throw away pieces of
bag.

Table #2: Indicator Test Result Table

Lipid
Carbohydrate Tests Protein Test
Test
Glucose Lipid
Sample Benedict’s Iodine Starch Biuret Protein
(sugar) present
test color test color present test color present
present (+’s) &
and (+’s) and (+’s) (Y/N) and (+’s) (Y/N)
(Y/N) (Y/N)
Vegetable oil

Glucose
Starch from corn
or potatoes
Powdered
egg whites
Water

Analysis#1: Table #1 vs. Table #2 Questions (Give complete and specific answers)
1. Does dH20 contain any macromolecules? Why did we test dH20 with each of the indicators?
2. Compare your testing results with the predictions you made in Table #1. Discuss any results that were not consistent
with your prediction and explain why you think this occurred.
3. Did your test for glucose indicate there was glucose in the starch sample? Does that mean that there is no glucose in
starch? (Hint: Check your textbook or other reliable source if you do not already know the chemical structure of
starch.)
4. Suppose that for the container containing water you found a positive test for one of the organic compounds. How
would you interpret this result?

Testing Different Types of Food and Testing the Evidence

Today you will perform all four organic compound tests on the foods listed below and the evidence John found at the
crime scene (your teacher will assign you a sample or samples to test). Begin by predicting which types of compounds
you expect to find in each type of food you will be testing. * - in order to simplify the testing process, all foods have been
made into a solution

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Table #3: Prediction for missing iPod

Do you expect this food to contain (include +’s for lot or

Food
little)
Glucose? Starch? Protein? Lipid?
Pretzel
Toast
Jelly (apricot)
Pineapple
Fat-free yogurt
Beans
Turkey
Swiss cheese
Fries (Potato)

Record your test results below in Table #4, using the same method as for testing the indicators.

Table #4: Evidence

Lipid
Carbohydrate Tests Protein Test
Test
Glucose Lipid
Food Benedict’s Iodine test Starch Biuret test Protein
(sugar) present
test color color and present color and present
present (+’s) &
and (+’s) (+’s) (Y/N) (+’s) (Y/N)
(Y/N) (Y/N)
Pretzel

Toast

Jelly

Pineapple

Fat-free yogurt
Beans

Turkey

Swiss Cheese

Gatorade
John’s unknown
evidence

Who took John’s iPod?

The workers in the break room are listed below with the type of lunch they were eating while John was studying. As
preparation for interpreting the evidence, complete the chart below to indicate what kinds of organic compounds are found
in each type of food and what kinds of organic compounds were found in the combined liquid + dry evidence. It may be
helpful to include the (+)’s. While some tests may show little difference, others might.

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Table #5: Suspects

Worker in
break Lunch/Snack Glucose Starch Protein Lipid
room
Frank Bean burrito with cheese
Ashley Fat-Free Yogurt
Bruce Jelly sandwich
Kiara Pretzel
Rose Pineapple
Vince Turkey and cheese sandwich
Wally Gatorade and Fries
Thief Evidence

Analysis #2: Post-lab Questions

In this activity you have recorded whether an indicator tested positive or negative for each type of organic compound. We
have ignored the fact that different foods contain different amounts of the various types of organic compounds. For
example, cream cheese and cottage cheese both have fat and protein, but cream cheese has much more fat than protein,
whereas cottage cheese has much more protein than fat. Most foods contain at least a tiny amount of proteins and lipids
since all cells in a plant or animal need to have at least some lipids and proteins.

5. Which compound(s) is most commonly in foods that come from plants? Animals?
6. If you want to reduce the amount of fat in your diet, what foods would you avoid?
7. Which foods tested would your body use for a quick burst of energy? Explain.
8. Which food tested would you use for energy if no carbohydrates are available? Explain.
9. Which food tested would you use for building body parts? Explain.
10. If one food tested positive for sugar and the indicator was greenish-yellow and another food tested positive for sugar
and the indicator was yellowish-orangish red, explain the difference in test results. You might review different types
of carbohydrates in the text.
11. Supposed you saved the water you cooked potatoes or pasta in. Explain color would it turn if mixed with Lugol’s?
12. Explain why there is no need to do a test for nucleic acids regardless of what food is tested?

13. Several tests are performed on a sample of whole milk. The results are shown in the table below. Based on these
results which macromolecules were present in the milk sample?
Indicator Result

Lugol’s Solution Orange / Brown

Benedict’s Solution Orange
Biuret Solution Purple
Paper Bag Translucent / Clear

14. A student conducted several tests on a piece of bacon. The results of his testing are shown in the table below.
Based on these results which molecules were present in the bacon?
Indicator Result
Lugol’s Solution Dark Purple / Black
Benedict’s Solution Light Blue
Biuret Solution Purple
Paper Bag Translucent / Clear

15. Which of the results of the students bacon experiment make you question his results? Explain.

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16. The lipid test you conducted today tests for triglycerides (fats and oils) specifically. Which foods tested contained
triglycerides? Which ones were saturated and which ones were unsaturated? How can you tell? What is the
molecular difference between saturated and unsaturated triglycerides?

Conclusion: Who took John’s iPod? Do you have any doubts about your conclusion? Include how you know about each
suspect. Include the test results in your explanation.

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