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Basics of Organic Chemistry question

2022 · 28 Jun · Shift 2 · Q7
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Basics of Organic Chemistry question

2022 · 28 Jun · Shift 2 · Q7

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The correct IUPAC name of the following compound is : JEE Main 2022 (Online) 28th June Evening Shift Chemistry - Basics of Organic Chemistry Question 143 English
  1. A
    4-methyl-2-nitro-5-oxohept-3-enal
  2. B
    4-methyl-5-oxo-2-nitrohept-3-enal
  3. C
    4-methyl-6-nitro-3-oxohept-4-enal
  4. D
    6-formyl-4-methyl-2-nitrohex-3-enal
View written solutionFree

Correct answer: C

  1. Identify the principal functional group

    The suffix must be chosen from the highest-priority functional group present.

    Given the options, the compound contains:

    • an aldehyde group, so the parent suffix will be -al,
    • a ketone group, which will be written as oxo (prefix),
    • a nitro substituent,
    • a methyl substituent,
    • a double bond.

    Therefore, the parent chain must include the aldehyde carbon and be numbered from that carbon as carbon-1.

  2. Choose the longest chain containing the aldehyde carbon

    From the options, the correct parent chain is a 7-carbon chain, so the parent hydrocarbon is heptanal derivative, not hexanal with a formyl substituent unless unavoidable.

    Hence option D is not preferred because IUPAC chooses the longest chain containing the principal functional group.

  3. Number the chain from the aldehyde carbon

    Since aldehyde has highest priority, numbering starts at the aldehyde carbon: C-1 = −CHO\text{C-1 = } -CHOC-1 = −CHO

    On examining the structure implied by the options, the substituents/unsaturation are placed as:

    • double bond at carbon 4: hept-4-enal,
    • ketone at carbon 3: 3-oxo,
    • methyl at carbon 4: 4-methyl,
    • nitro at carbon 6: 6-nitro.
  4. Write the name in proper IUPAC order

    Prefixes are written alphabetically:

    • methyl
    • nitro
    • oxo

    But the functional unsaturation and suffix are part of the parent name. Thus the complete name becomes: 4-methyl-6-nitro-3-oxohept-4-enal\boxed{\text{4-methyl-6-nitro-3-oxohept-4-enal}}4-methyl-6-nitro-3-oxohept-4-enal​

  5. Check options

    • A: 444-methyl-222-nitro-555-oxohept-333-enal → incorrect locants.
    • B: same locants as A, only different ordering → still incorrect.
    • C: 444-methyl-666-nitro-333-oxohept-444-enal → correct.
    • D: uses hex chain with formyl substituent, not preferred over longest parent chain containing aldehyde.
  6. Final answer

    The correct IUPAC name is: 4-methyl-6-nitro-3-oxohept-4-enal\boxed{\text{4-methyl-6-nitro-3-oxohept-4-enal}}4-methyl-6-nitro-3-oxohept-4-enal​ So the correct option is C.

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