VCE Chemistry Units

Biomacromolecules IV

Week 13

Objectives: I. II. Biochemical Fuels Review DNA b. a. Restriction enzymes Medical Chemistry a. Aspirin i. Synthesis

III.

IV. V.

Revision of Unit 3

ii. Solubility

Test II Revision of Unit 3

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Horizen Education | VCE Chemistry Units 3 and 4 | Biomacromolecules IV

Review Questions
Question 1 Draw the structural formula of a deoxyribose sugar. Indicate where covalent bonds form to link this group b) A base group to: a) A phosphate group

Question 2 and pyrimidine

List the two purine and two pyrimidine bases and describe the difference in structure between a purine

_________________________________________________________________________________________________ _________________________________________________________________________________________________ _________________________________________________________________________________________________ Question 3 Which of the following incorrectly pairs bonding type to protein structure Form of bonding Covalent bonding only H-bonding, dipole-dipole, covalent, dispersion Covalent bonding, dipole-dipole, H-bonding, Ion-dipole

Structure Type A. B. C. Primary Structure Secondary Structure Tertiary Structure

Question 4

Give the correct bonding type for the incorrectly paired choice from the question above.

A. H-bonding B. Covalent C. Side chain interactions D. All of the above Question 5 In terms of the structure of the four nitrogenous bases, explain how the two single polymer DNA chains

cause complementary base pairing and bring about symmetry along the length of the DNA double helix molecule. _________________________________________________________________________________________________ _________________________________________________________________________________________________ _________________________________________________________________________________________________ _________________________________________________________________________________________________

Horizen Education | VCE Chemistry Units 3 and 4 | Biomacromolecules IV Question 6 Gel electrophoresis is a technique that can be used to separate DNA fragments in forensic chemistry. The

gel resulting from such a separation experiment carried out at pH 7 is shown below.

Which of the following statements about the experiment is not correct? A. Fragment X has a higher molecular mass than fragment Y. B. Fragment Y moves through the gel at a faster rate than fragment X. C. The negative terminal of the power supply is connected to end A of the gel. D. Under the conditions of this experiment, the DNA fragments are positively charged.

Biochemical Fuels
Question 1 a. b. c. d. Biodiesel is a chemical biofuel derived from vegetable oils reacted with methanoic acid. Which of the following statements is TRUE? Biodiesel is a non-renewable and unsustainable resource that propagates greenhouse emissions Biodiesel is cheaper to produce than standard liquid petroleum Potassium hydroxide and water is added to the vegetable oil to hydrolyse the bond and methanol is then added to form the biodiesel ester Each single triglyceride of vegetable oil produces one biodiesel molecules and one molecule of water (6 marks)

Question 2 a.

Biodiesel is a methyl ester of a vegetable fatty acid. Describe a potential reaction pathway for the synthesis of biodiesel from vegetable oil. Indicating all catalysts and reagents (3 marks) ___________________________________________________________________________________________ ___________________________________________________________________________________________ ___________________________________________________________________________________________ 3

Horizen Education | VCE Chemistry Units 3 and 4 | Biomacromolecules IV b. Briefly describe the advantages and disadvantages of using biodiesel in replacement of conventional petrol in cars (3 marks) ___________________________________________________________________________________________ ___________________________________________________________________________________________ ___________________________________________________________________________________________

Aspirin
One of the most popular modern drugs to help with pain relief was discovered millennia ago by the Greek physician Hippocrates. The pain-relieving and anti-inflammatory chemical was first discovered in the bark of willow trees. Today, the exact chemical producing this effect is known as salicylic acid. Salicylic acid is known to have an extremely unpleasant bitter taste and cause irritation of the mouth, which is why the pure form aspirin was formed. Question Why is aspirin preferred over salicylic acid? List the pathway of aspirin digestion in the body

To synthesise a medicine, chemists must consider the biochemical pathway in which it is absorbed into the body. The faster the uptake of the medicine, the more effective it is in treatment. For this reason, aspirin is synthesised using ethanoic anhydride via a condensation reaction instead of using ethanoic acid. Example Draw out the reaction pathway to form aspirin from salicylic acid and acetic anhydride

Question

What type of reaction occurs when aspirin is digested in the body?

Steps in synthesising aspirin (SAC 3)

1. Extract salicylic acid from willow bark 2. React the salicylic acid and acetic anhydride in the presence of a catalyst, H3PO4 3. Once the reaction is completed, aspirin is isolated from the reaction solution and purified by addition of chilled water and filtering the reaction solution. 4. Purification is accomplished by recrystallization dissolving the aspirin in warm ethanol and then slowly cooling the solution to crystallise out the aspirin. This leaves the impurities behind. 4

Horizen Education | VCE Chemistry Units 3 and 4 | Biomacromolecules IV Determination of Purity The melting point of a pure sample of aspirin will be much higher than that of an impure compound. Therefore the melting point of aspirin can be used to determine its purity. Therefore, if your sample melts at a temperature lower than the accepted melting point, two possibilities exist: either your product is impure or it is not aspirin. A pure substance will melt sharply over a range of 1 or 2 degrees Celsius. Example How is the synthesised aspirin purified before it is sold? Why is this step taken?

_________________________________________________________________________________________________ _________________________________________________________________________________________________ Question Explain why the process using ethanoic anhydride is preferred over the one using ethanoic acid

_________________________________________________________________________________________________ _________________________________________________________________________________________________

Sodium Salt of Aspirin

The sodium salt of aspirin is a more soluble form of aspirin that can be formed by hydrolysing the COOH functional group of the aspirin molecule and attaching a Na+ group to the ionic form of many medicines makes it more soluble in the body. Many medicines will be used in an ionised form often as a sodium salt or ionised with the basic amino acid lysine. Example Briefly explain why the sodium salt/ ionic form of aspirin is more soluble in water than the COOH

functional group.

Example

Draw the sodium salt structure of aspirin

Horizen Education | VCE Chemistry Units 3 and 4 | Biomacromolecules IV

In Class Problems (Revision of AOS 2)

Question 1 (Source: VCAA Chemistry 2011 Exam 1 MCQ 8)

Question 2

Medical proteins such as insulin are administered by injection. Using your knowledge of proteins, suggest

why they cannot be given orally in tablet form? _________________________________________________________________________________________________ _________________________________________________________________________________________________ _________________________________________________________________________________________________ 6

Horizen Education | VCE Chemistry Units 3 and 4 | Biomacromolecules IV Question 3 (Source: VCAA Chemistry Exam 1 2009 pg. 20)

Question 4

Distinguish the difference between protein primary, secondary, and tertiary structure, providing a

drawing for each. _________________________________________________________________________________________________ _________________________________________________________________________________________________ _________________________________________________________________________________________________ _________________________________________________________________________________________________

Horizen Education | VCE Chemistry Units 3 and 4 | Biomacromolecules IV Question 5 A biomolecule is chemically analysed and found to contain only the elements of carbon, hydrogen,

oxygen, nitrogen and phosphorus. The biomolecule is most likely A. DNA. B. A Protein C. A polysaccharide D. A fat formed by condensation of glycerol with stearic acid.\ Question 6 Is DNA analysis conducted on the coding or noncoding strand of DNA? Explain your choice.

_________________________________________________________________________________________________ _________________________________________________________________________________________________ Question 7 cells die. I. II. III. IV. A high level of CPK in the blood must mean the patient has heart disease. A person suffering a heart attack would likely have higher than average levels of CPK in the blood. A doctor can diagnose the effectiveness of a treatment by monitoring the CPK levels. Elevated levels of CPK in the body cause heart disease. Consider the following statements about CPK (creatine phosphokinase) an enzyme commonly found as a

disease marker for heart disease. It is found in human heart muscle, skeletal muscle, and in the brain and released when

Which of the following statements are true? A. I, II, III B. II only C. II and III only D. All of the above Question 8 a. b. c. d. A single nucleotide of DNA contains DNA double helix strand segment wrapped around a histone protein Phosphate group, deoxyribose sugar, and nitrogenous base Phosphate group, deoxyribose sugar Glycerol and three fatty acids