Q.19 - An Introduction to General, Organic, and Biological Chemistry

Question

Tamiflu (oseltamivir), ${\mathrm{C}}_{16}{\mathrm{H}}_{28}{\mathrm{N}}_2{\mathrm{O}}_4$ is an antiviral drug used to treat influenza. The preparation of Tamiflu begins with the extraction of shikimic acid from the seedpods of star anise. From 2.6g of star anise, 0.13g of shikimic acid can be obtained and used to produce one capsule containing 75mg of Tamiflu. The usual adult dosage for treatment of influenza is two capsules of Tamiflu daily for 5 days. 

a. If black spheres are carbon atoms, white spheres are hydrogen atoms, and red spheres are oxygen atoms, what is the formula of shikimic acid?

b. What is the molar mass of shikimic acid?

c. How many moles of shikimic acid are contained in 130g of shikimic acid?

d. How many capsules containing 75mg of Tamiflu could be produced from 155g of star anise?

e. What is the molar mass of Tamiflu?

f. How many kilograms of Tamiflu would be needed to treat all the people in a city with a population of 500000 if each person consumes two Tamiflu capsules a day for 5 days?

Step-by-Step Solution

Answer

Part a. ${\mathrm{C}}_7{\mathrm{H}}_{10}{\mathrm{O}}_5$

Part b. $174 g/ml$

Part c. $0.747$moles

Part d. $60$ capsules

Part e. $312 g/mole$

Part f.  $375 kg$

Step 1: Given Information (Part a)

Shikimic acid is a cyclohexene, a cyclitol and a cyclohexane carboxylic acid. It is a significant biochemical metabolite in plants and microorganisms. Its name is derived from the flower shikimi in Japan.

Step 2: Explanation Part (a)

The formula of shikimic acid is $C_7{H}_{10}{O}_5$.

Step 3: Explanation Part (b)

We know,

C= $12 g$

H= $1 g$

O= $16 g$

The molar mass of shikimic acid is 

$(7\times 12)+(10\times 1)+(5\times 16)=174 \mathrm{g}/\mathrm{mol}$

Step 4: Explanation Part (c)

We know,

Mass = $130 g$

Molar mass = $174 g/ml$

$\text{ Moles }=\frac{\text{ mass }}{\text{ molar mass }}=\frac{130 \mathrm{g}}{174 \mathrm{g}/\mathrm{mole}}=0.747\text{ moles }$

Step 5: Explanation Part (d)

Given,

$2.6 g$ of star anise contains $75 mg$ Tamiflu

$155$gram of star anise contains =$=155\times \frac{1}{2.6}=60$

Hence, $60$ capsules are obtained.

Step 6: Explanation Part (e)

We know,

C= $12 g$

O= $16 g$

H= $1 g$

N=$14 g$

Molar mass Tamiflu = $(16\times 12)+(28\times 1)+(4\times 16)+(2\times 14)=312 \mathrm{g}/\mathrm{mole}$

Step 7: Explanation Part (f)

Given,

The population =$500000$

each person consumes two Tamiflu capsules a day for $5$ days.

Each person consumes = $2\times 5=10$capsules

Mass of capsule = $75 g$

Mass of capsule consumed by each person = $10\times 75=750 g$

The total mass of Tamiflu would be needed to treat all the people in a city is

$500000\times 750=37500000 mg =375 kg$