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
The chiral center in prilocaine is the carbon atom attached to both the CH3 and NH group. Circle this carbon in Figure 3.
Step 2
Identify the functional group(s) in the prilocaine molecule.
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Answer
In the prilocaine molecule, the functional groups present are an amide and an ester.
Step 3
Draw the structures of the two organic products formed in the complete hydrolysis of prilocaine in acidic conditions.
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Answer
The two organic products of the complete hydrolysis of prilocaine in acidic conditions are:
A protonated amino acid (R-NH3^+COOH)
An acid (R-COOH)
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 specifically shaped to complement the structure of isomer G, allowing it to facilitate the hydrolysis of G efficiently. Isomer F, having a different spatial configuration due to its chirality, does not fit into the active site of the enzyme, preventing its hydrolysis.
