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 centre in prilocaine is the carbon atom attached to the nitrogen (N) and the carbon chain (C), which should be circled.
Step 2
Identify the functional group(s) in the prilocaine molecule.
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Answer
The functional groups present in prilocaine are Amide and Amine. Therefore, the boxes corresponding to 'Amide' and 'Amine' should be ticked.
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 formed will be:
A protonated amino acid:
H3N^+ - C - COOH
|
R
Another carboxylic acid (consider structural variations based on prilocaine's hydrolysis).
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 specifically fits the structural configuration of isomer G, allowing it to effectively bind and catalyse its hydrolysis. In contrast, the active site does not accommodate isomer F due to differences in stereochemistry or shape.
