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Higher 3 Concept Test

Higher 3 Concept Test

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Published by OccamsRazor
Grammatical mistakes - Q2: hypothesised; Q3- one of the benzene ring protons
Grammatical mistakes - Q2: hypothesised; Q3- one of the benzene ring protons

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Published by: OccamsRazor on Dec 06, 2010
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Higher 3 Pharmaceutical Chemistry Concept Test 1

Answer all three questions. Question 1 and 2 are worth 20 marks each and question 3 is worth only 10 marks.

Time: 1h 15 mins


Acknowledgements Nil

Question 1 Imines are important intermediates in metabolism and synthesis of drug molecules. Imines can be seen as a µhybrid¶ between nitriles and amine.

Acyclovir is an example of a drug with imine groups. Copy down the structure of acyclovir and circle the imine groups [1] Other than the imine functional groups, state four other functional groups present in acyclovir. [2]
A with propanone can form B, C5H11N and C, C8H15NOBr. C, being so unstable would undergo an elimination reaction which is part of the Mannich reaction to form an iminium ion, D.

The Hinsberg test can be used to distinguish between the primary, secondary and tertiary amines. The results of the test are given below:

y y y

When C6H5SO2Cl is added to a primary amine a clear solution is obtained but upon addition of acid, precipitation occurs. When C6H5SO2Cl is added to a secondary amine a cloudy solution is obtained and upon addition of acid, the solution remains cloudy. When C6H5SO2Cl is added to a tertiary amine a cloudy solution is obtained but upon addition of acid, the solution becomes clear.

When A reacts with C6H5SO2Cl, result 2 is obtained. When B is tested, result 3 is obtained. Further given that B is a 5-membered ring, suggest the structures of A, B, C and D. [6] Suggest the mechanism of the formation of B from A. [2] Suggest the mechanism of C to D. [2] 3-(ethylamino)phenol can react with methanal to form a bicyclic ring system through electrophilic substitution of an imine intermediate . Suggest the mechanism of this reaction. [2] There is no need to show the imine formation.

Penicillins and cephalosporins have bicyclic ring systems. Cephalosporins have a less strained beta-lactam ring, suggest why? [1]

Explain how cephalosporins work against bacterias. [1] Explain the use of prodrugs in the context of penicillins. [2] Name an example of an anti-metabolite and a translational inhibitor. [1]

[Total: 20m]

Question 2

It is hypothesise that depression is caused by serotonin and noradrenaline which are monoamine neurotransmitters. Therefore the use of monoamine oxidase (MAO) inhibitors may be the basis of antidepressants. Suggest why nicotine may relieve depression. [1] Using the diagram provided suggest one other way that drug can relieve depression [3]

In the ³amine hypothesis´, serotonin and noradrenaline are not sufficiently transferred to the post synaptic neurons, leading to depression. However serotonin activity reducing agent like trazodone (receptor anatagonist) and taineptine (serotonin reuptake enhancers) can help against depression. Explain why these two drugs are µconflicting treatments¶. [3] Suggest why the pharmacodynamics of anti-depressants are still a mystery. [1] Another hypothesis that supports such conflicting treatments states that overactivation of a subtype of serotonin receptors can lead to depression. Using the theory above and µtheory of tolerance¶ explain why MAO inhibitor works despite the theory. [2] Depressants are the exact opposite of anti -depressants. One common depressant is ethanol. There are many ways to detect ethanol in one¶s breath. One way is through the intoximeter, which uses IR spectroscopy. Explain the origin of IR spectroscopy. [2]
y y

The person breathes into the infrared spectrometer Absorption of infrared (IR) radiation of a specific wavelength by the -O-H bond in the ethanol produces a characteristic peak on the spectrum. The amount of absorption depends on the concentration of ethanol in the breath Ethanol is compared with air or a reference sample to determine if it is over the allowed amount


Write an equilibrium constant expression for this test. [1]

Draw the IR spectrum of ethanol ± showing the characteristics of the O-H, C-H and C-O stretches. [3] Another way is through GLC (blood and urine) in the laboratory. Explain in context how this works. [2] Roadside breathalysers uses compounds that contain the transition metal chromium to detect ethanol. Suggest the ionic equation of this reaction and state the colour change that is witnessed. [ 2]

Question 3 Copy and fill out the table below :

Physiological measurement Respiration rate Heart rate Blood pressure Blood flow Effect on bronchi Appetite Urine flow Sleep patterns Blood sugar



Deduce the structure of the analgesic using the information given [7].
H 11.3 6.4-7.8 2.0 1.3

Integral 1 9 1 3

Multiplicity singlet multiplet quartet doublet

M M+1

100% abundance 16.5% abundance

It is cleaved by acid to form 2 phenols. It evolves carbon dioxide when bicarbonate is added to it.

It is also given that one of the benzene ring proton is in between the side chain and the ether group.

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