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Basics of Organic Chemistry question

2020 · 6 Sep · Shift 2 · Q6
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Basics of Organic Chemistry question

2020 · 6 Sep · Shift 2 · Q6

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPAC name of the following compound is : JEE Main 2020 (Online) 6th September Evening Slot Chemistry - Basics of Organic Chemistry Question 178 English
  1. A
    2-nitro-4-hydroxymethyl-5-amino benzaldehyde
  2. B
    3-amino-4-hydroxymethyl-5-nitro benzaldehyde
  3. C
    4-amino-2-formyl-5-hydroxymehtyl nitrobenzene
  4. D
    5-amino-4-hydroxymethyl-2-nitro benzaldehyde
View written solutionFree

Correct answer: D

  1. Identify the principal functional group

    The compound contains a −CHO-CHO−CHO group, so the parent compound is benzaldehyde.

    Hence, numbering of the benzene ring starts from the carbon attached to the aldehyde group as carbon 111.

  2. Identify the substituents

    From the structure/options, the substituents present on the benzaldehyde ring are:

    • −NO2-NO_2−NO2​ = nitro
    • −NH2-NH_2−NH2​ = amino
    • −CH2OH-CH_2OH−CH2​OH = hydroxymethyl
  3. Assign locants

    With −CHO-CHO−CHO at position 111, the substituents are located at:

    • nitro at 222
    • hydroxymethyl at 444
    • amino at 555

    So the locant set is 2,4,52,4,52,4,5.

  4. Write substituents in alphabetical order

    Prefixes are arranged alphabetically:

    • amino
    • hydroxymethyl
    • nitro

    Therefore, the systematic name becomes: 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde5\text{-amino-}4\text{-hydroxymethyl-}2\text{-nitrobenzaldehyde}5-amino-4-hydroxymethyl-2-nitrobenzaldehyde

  5. Check the options

    • A: 2-nitro-4-hydroxymethyl-5-amino benzaldehyde
      Same locants, but substituents are not written in proper alphabetical order.
    • B: 3-amino-4-hydroxymethyl-5-nitro benzaldehyde
      Wrong numbering.
    • C: 4-amino-2-formyl-5-hydroxymehtyl nitrobenzene
      Incorrect parent naming and numbering.
    • D: 5-amino-4-hydroxymethyl-2-nitro benzaldehyde
      Correct numbering and proper order.
  6. Final answer

    The correct IUPAC name is: 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde\boxed{\text{5-amino-4-hydroxymethyl-2-nitrobenzaldehyde}}5-amino-4-hydroxymethyl-2-nitrobenzaldehyde​

    So, option D is correct.

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