
- A2-carboxy-4-hydroxyhept-7-enal
- B2-formyl-4-hydroxyhept-7-enoic acid
- C2-carboxy-4-hydroxyhept-6-enal
- D2-formyl-4-hydroxyhept-6-enoic acid
View written solutionFree
Correct answer: D
-
Identify the highest priority functional group
The options indicate the compound contains:
- a carboxylic acid group,
- an aldehyde group,
- a hydroxy group,
- and a double bond.
By IUPAC priority, carboxylic acid has higher priority than aldehyde and alcohol. So the parent suffix must be -oic acid.
Hence, options with suffix enal are incorrect.
Therefore, A and C are eliminated.
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Choose the parent chain and numbering
Since the principal functional group is carboxylic acid, numbering starts from the carboxyl carbon as carbon 1.
The parent chain has 7 carbons, so the base name is heptenoic acid.
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Locate the double bond
Numbering from the carboxylic acid end, the double bond lies between carbon 6 and carbon 7.
Therefore the parent is hept-6-enoic acid.
So B (hept-7-enoic acid) is impossible, because a 7-carbon chain cannot have a double bond starting at carbon 7.
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Identify the substituents
- The aldehyde group, when not principal, is named as formyl.
- The hydroxy substituent is named hydroxy.
From the structure/options:
- formyl is at carbon 2,
- hydroxy is at carbon 4.
So the name becomes:
-
Check all options
- A: 2-carboxy-4-hydroxyhept-7-enal → wrong principal group and impossible double bond position.
- B: 2-formyl-4-hydroxyhept-7-enoic acid → wrong double bond position.
- C: 2-carboxy-4-hydroxyhept-6-enal → wrong principal group.
- D: 2-formyl-4-hydroxyhept-6-enoic acid → correct.
Final Answer
The correct nomenclature is:
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