Prilocaine is used as an anaesthetic in dentistry. Figure 3 shows the structure of prilocaine. Draw a circle around any chiral centre(s) in Figure 3. Identify the functional group(s) in the prilocaine molecule. Tick ('✓') the box(es) corresponding to the functional group(s). Prilocaine is completely hydrolysed in the human body to give a mixture of products. Draw the structures of the two organic products formed from the complete hydrolysis of prilocaine in acidic conditions. Figure 4 shows optical isomers F and G. Isomer F is the active compound in the medicine ibuprofen. In the manufacture of ibuprofen both isomers F and G are formed. An enzyme is then used to bind to isomer G and catalyse its hydrolysis. After the products of hydrolysis of G are removed, a pure sample of isomer F is collected. Explain how a structural feature of this enzyme enables it to catalyse the hydrolysis of isomer G but not the hydrolysis of isomer F.

A-Level AQA Chemistry Optical Isomerism: Prilocaine is used as an anaesth

Prilocaine is used as an anaesthetic in dentistry - AQA - A-Level Chemistry - Question 2 - 2020 - Paper 2

Question 2

Prilocaine is used as an anaesthetic in dentistry. Figure 3 shows the structure of prilocaine. Draw a circle around any chiral centre(s) in Figure 3. Identify the ... show full transcript

Worked Solution & Example Answer:Prilocaine is used as an anaesthetic in dentistry - AQA - A-Level Chemistry - Question 2 - 2020 - Paper 2

Step 1

Draw a circle around any chiral centre(s) in Figure 3

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Answer

Identify and circle the carbon atom attached to four different substituents (the chiral center) in the prilocaine structure.

Step 2

Identify the functional group(s) in the prilocaine molecule

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Answer

The functional groups present in the prilocaine molecule are: amide and ester.

Step 3

Draw the structures of the two organic products formed from the complete hydrolysis of prilocaine in acidic conditions

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Answer

The two organic products from the hydrolysis of prilocaine in acidic conditions are:

A protonated amino acid derived from the amine functional group of prilocaine.
An acid formed from the ester group.

Step 4

Explain how a structural feature of this enzyme enables it to catalyse the hydrolysis of isomer G but not the hydrolysis of isomer F

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Answer

The enzyme has an active site that is specifically shaped to fit isomer G, allowing it to bind effectively and catalyse its hydrolysis. The structural feature that allows this specificity is likely due to the arrangement of functional groups that facilitate binding to only G, while isomer F does not fit properly in the active site.

Prilocaine is used as an anaesthetic in dentistry - AQA - A-Level Chemistry - Question 2 - 2020 - Paper 2

Worked Solution & Example Answer:Prilocaine is used as an anaesthetic in dentistry - AQA - A-Level Chemistry - Question 2 - 2020 - Paper 2

Draw a circle around any chiral centre(s) in Figure 3

Identify the functional group(s) in the prilocaine molecule

Draw the structures of the two organic products formed from the complete hydrolysis of prilocaine in acidic conditions

Explain how a structural feature of this enzyme enables it to catalyse the hydrolysis of isomer G but not the hydrolysis of isomer F

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