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Basics of Organic Chemistry question

2024 · 31 Jan · Shift 1 · Q19
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Basics of Organic Chemistry question

2024 · 31 Jan · Shift 1 · Q19

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Given below are two statements: Statement I: IUPAC name of HO−CH2−(CH2)3−CH2−COCH3\mathrm{HO}-\mathrm{CH}_2-\left(\mathrm{CH}_2\right)_3-\mathrm{CH}_2-\mathrm{COCH}_3HO−CH2​−(CH2​)3​−CH2​−COCH3​ is 7-hydroxyheptan-2-one. Statement II: 2-oxoheptan-7-ol is the correct IUPAC name for above compound. In the light of the above statements, choose the most appropriate answer from the options given below:
  1. A
    Statement I is incorrect but Statement II is correct.
  2. B
    Statement I is correct but Statement II is incorrect.
  3. C
    Both Statement I and Statement II are correct.
  4. D
    Both Statement I and Statement II are incorrect.
View written solutionFree

Correct answer: B

  1. Write the structure clearly

    The given compound is: HO−CH2−(CH2)3−CH2−COCH3\mathrm{HO-CH_2-(CH_2)_3-CH_2-COCH_3}HO−CH2​−(CH2​)3​−CH2​−COCH3​

    Expanding it: HO−CH2−CH2−CH2−CH2−CH2−CO−CH3\mathrm{HO-CH_2-CH_2-CH_2-CH_2-CH_2-CO-CH_3}HO−CH2​−CH2​−CH2​−CH2​−CH2​−CO−CH3​

    So the longest chain containing the carbonyl carbon has 7 carbon atoms.

  2. Identify the principal functional group

    The compound contains:

    • an alcohol group (−OH)(-OH)(−OH)
    • a ketone group (>C=O)(>C=O)(>C=O)

    In IUPAC priority, ketone has higher priority than alcohol.

    Therefore, the parent name must use the suffix -one, and the −OH-OH−OH group will be named as the prefix hydroxy.

  3. Number the chain correctly

    Since ketone is the principal functional group, numbering must give the carbonyl carbon the lowest possible locant.

    Numbering from the methyl ketone end:

    CH3−CO−CH2−CH2−CH2−CH2−CH2OH\mathrm{CH_3-CO-CH_2-CH_2-CH_2-CH_2-CH_2OH}CH3​−CO−CH2​−CH2​−CH2​−CH2​−CH2​OH

    This gives:

    • ketone at carbon 2
    • hydroxy at carbon 7

    Hence the correct IUPAC name is: 7-hydroxyheptan-2-one\boxed{7\text{-hydroxyheptan-2-one}}7-hydroxyheptan-2-one​

  4. Check Statement I

    Statement I says: IUPAC name is 7-hydroxyheptan-2-one.

    This is correct.

  5. Check Statement II

    Statement II says: 2-oxoheptan-7-ol is the correct IUPAC name.

    This is incorrect, because:

    • using suffix -ol makes alcohol the principal functional group,
    • but ketone has higher priority than alcohol.

    So the compound should not be named as an alcohol with an oxo substituent.

  6. Evaluate the options

    • A: Statement I incorrect, Statement II correct →\rightarrow→ false
    • B: Statement I correct, Statement II incorrect →\rightarrow→ true
    • C: Both correct →\rightarrow→ false
    • D: Both incorrect →\rightarrow→ false

Therefore, the correct option is: B\boxed{\text{B}}B​

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