
- A3-Bromo-5-methylcyclopentane carboxylic acid
- B3-Bromo-5-methylcyclopentanoic acid
- C4-Bromo-2-methylcyclopentane carboxylic acid
- D5-Bromo-3-methylcyclopentanoic acid
View written solutionFree
Correct answer: C
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Identify the principal functional group
The compound contains a carboxylic acid group, .
When a group is attached to a ring and the carbon of the carboxyl group is not part of the ring, the correct IUPAC form is: So the parent name must be of the form:
Hence, options with cyclopentanoic acid are incorrect.
Therefore, B and D are eliminated.
-
Fix the numbering of the ring
In cycloalkane carboxylic acids, the ring carbon attached to the group is numbered as C-1.
Now number the ring in the direction that gives the substituents the lowest set of locants.
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Locate the substituents
From the given structure, the substituents on the cyclopentane ring are:
- one methyl group
- one bromo group
Taking the carbon attached to as C-1, numbering in the correct direction gives:
- methyl at C-2
- bromo at C-4
So the name becomes:
-
Check with options
- A: -Bromo--methylcyclopentane carboxylic acid incorrect locants
- B: -Bromo--methylcyclopentanoic acid wrong parent suffix
- C: -Bromo--methylcyclopentane carboxylic acid correct
- D: -Bromo--methylcyclopentanoic acid wrong parent suffix
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Final answer
-
Comparison with stored correct answer
Stored correct answer: C
My derived answer: C
Hence, they agree.
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