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Basics of Organic Chemistry question

2004 · Shift 0 · Q25
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Basics of Organic Chemistry question

2004 · Shift 0 · Q25

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Rate of the reaction AIEEE 2004 Chemistry - Basics of Organic Chemistry Question 236 English is fastest when ZZZ is
  1. A
    OC2H5O{C_2}{H_5}OC2​H5​
  2. B
    NH2N{H_2}NH2​
  3. C
    ClClCl
  4. D
    OCOCH3OCOC{H_3}OCOCH3​
View written solutionFree

Correct answer: C

  1. Identify the reaction type

    The question asks: "Rate of the reaction is fastest when ZZZ is ..." with substituents Z=OC2H5, NH2, Cl, OCOCH3Z = OC_2H_5,\, NH_2,\, Cl,\, OCOCH_3Z=OC2​H5​,NH2​,Cl,OCOCH3​

    This standard type of question in basic organic chemistry usually refers to electrophilic aromatic substitution on an aromatic ring, where the substituent ZZZ already present on the ring affects the reaction rate.

  2. Recall the effect of substituents on ring activation/deactivation

    In electrophilic aromatic substitution:

    • Electron-donating groups activate the ring and increase the rate.
    • Electron-withdrawing groups deactivate the ring and decrease the rate.

    Compare the given groups:

    • −NH2-NH_2−NH2​ : very strong +M+M+M (resonance donation), strongly activating
    • −OC2H5-OC_2H_5−OC2​H5​ : strong +M+M+M, activating
    • −OCOCH3-OCOCH_3−OCOCH3​ : oxygen is attached to ring, but its lone pair is partly tied up with the carbonyl; still o/p-directing but less activating than alkoxy/amino
    • −Cl-Cl−Cl : has lone-pair resonance donation, but strong −I-I−I effect dominates; overall deactivating
  3. Order of activation

    The approximate reactivity order is NH2>OR>OCOCH3>ClNH_2 > OR > OCOCH_3 > ClNH2​>OR>OCOCH3​>Cl

    Therefore, the aromatic ring reacts fastest when Z=NH2Z = NH_2Z=NH2​

  4. Check each option

    • A: OC2H5OC_2H_5OC2​H5​ — activating, but not the strongest
    • B: NH2NH_2NH2​ — strongest activator among the options ✅
    • C: ClClCl — deactivating, so not fastest
    • D: OCOCH3OCOCH_3OCOCH3​ — weaker activator than OROROR and NH2NH_2NH2​
  5. Derived answer

    Hence, the rate is fastest for NH2\boxed{NH_2}NH2​​

  6. Comparison with stored correct answer

    Stored correct answer is C (ClClCl).

    This does not match the standard substituent effect in electrophilic aromatic substitution. Unless the missing reaction scheme is of some unusual type where ClClCl specifically accelerates the reaction, the chemically correct answer from the given substituent effects is B (NH2NH_2NH2​).

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