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Basics of Organic Chemistry question

2002 · Shift 0 · Q13
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Basics of Organic Chemistry question

2002 · Shift 0 · Q13

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Arrangement of (CH3)3C−(CH_3)_3C^-(CH3​)3​C−, (CH3)2CH−(CH_3)_2CH^-(CH3​)2​CH−, CH3−CH2−CH_3-CH_2-CH3​−CH2​− when attached to benzyl or an unsaturated group in increasing order of inductive effect is
  1. A
    (CH3)3C−(CH_3)_3C^-(CH3​)3​C− < (CH3)2CH−(CH_3)_2CH^-(CH3​)2​CH− < CH3−CH2CH_3-CH_2CH3​−CH2​
  2. B
    CH3−CH2−CH_3-CH_2-CH3​−CH2​− < (CH3)2CH−(CH_3)_2CH^-(CH3​)2​CH− < (CH3)3C−(CH_3)_3C^-(CH3​)3​C−
  3. C
    (CH3)2CH(CH_3)_2CH(CH3​)2​CH- < (CH3)3C(CH_3)_3C(CH3​)3​C- < CH3CH_3CH3​-CH2CH_2CH2​
  4. D
    (CH3)3C(CH_3)_3C(CH3​)3​C- < CH3CH_3CH3​-CH2CH_2CH2​- < CH3CH_3CH3​)2CHCHCH-
View written solutionFree

Correct answer: B

  1. Concept involved: Inductive effect of alkyl groups

    Alkyl groups attached to a benzyl or unsaturated system show a +I+I+I effect (electron-releasing inductive effect).

    The magnitude of +I+I+I effect of alkyl groups generally depends on the degree of alkyl substitution:

    tertiary alkyl>secondary alkyl>primary alkyl\text{tertiary alkyl} > \text{secondary alkyl} > \text{primary alkyl}tertiary alkyl>secondary alkyl>primary alkyl

  2. Identify the given groups

    The groups are:

    • CH3CH2−CH_3CH_2-CH3​CH2​− : ethyl group = primary alkyl
    • (CH3)2CH−(CH_3)_2CH-(CH3​)2​CH− : isopropyl group = secondary alkyl
    • (CH3)3C−(CH_3)_3C-(CH3​)3​C− : tert-butyl group = tertiary alkyl

  3. Apply the order of +I+I+I effect

    Since inductive electron donation increases with branching:

    CH3CH2−<(CH3)2CH−<(CH3)3C−CH_3CH_2- < (CH_3)_2CH- < (CH_3)_3C-CH3​CH2​−<(CH3​)2​CH−<(CH3​)3​C−

  4. Match with the options

    This corresponds to Option B.

  5. Final answer

    Increasing order of inductive effect:

    CH3CH2−<(CH3)2CH−<(CH3)3C−CH_3CH_2- < (CH_3)_2CH- < (CH_3)_3C-CH3​CH2​−<(CH3​)2​CH−<(CH3​)3​C−

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