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Hydrocarbons question

2005 · Shift 0 · Q15
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Hydrocarbons question

2005 · Shift 0 · Q15

JEE MainChemistryHydrocarbonsMCQ+4 / −1
2 methylbutane on reacting with bromine in the presence of sunlight gives mainly
  1. A
    1 – bromo -2 - methylbutane
  2. B
    2 – bromo -2 - methylbutane
  3. C
    2 – bromo -3 - methylbutane
  4. D
    1 – bromo -3 – methylbutane
View written solutionFree

Correct answer: B

  1. Identify the reaction type

    Bromine in the presence of sunlight (hνh\nuhν) reacts with alkanes by free radical substitution.

    So, in 222-methylbutane, one of the hydrogen atoms is replaced by bromine.

  2. Write the structure of 222-methylbutane

    2-methylbutane=CH3−CH(CH3)−CH2−CH3\text{2-methylbutane} = CH_3-CH(CH_3)-CH_2-CH_32-methylbutane=CH3​−CH(CH3​)−CH2​−CH3​

    Numbering the carbon chain:

    CH3−CH(CH3)−CH2−CH3CH_3-CH(CH_3)-CH_2-CH_3CH3​−CH(CH3​)−CH2​−CH3​   12 34\ \,1\quad 2\qquad\, 3\qquad 4 1234

    Carbon 222 is attached to three carbons, so it is a tertiary carbon and has one tertiary hydrogen.

  3. Find the different types of hydrogens

    In 222-methylbutane, we have:

    • 1 tertiary hydrogen at carbon 222
    • 2 secondary hydrogens at carbon 333
    • 9 primary hydrogens on the three methyl groups
  4. Use selectivity of bromination

    Bromination is highly selective. The reactivity order is:

    3∘>2∘>1∘3^\circ > 2^\circ > 1^\circ3∘>2∘>1∘

    Therefore, bromine substitutes mainly at the tertiary hydrogen position.

  5. Form the major product

    Replacing the tertiary hydrogen at carbon 222 by bromine gives:

    CH3−C(Br)(CH3)−CH2−CH3CH_3-C(Br)(CH_3)-CH_2-CH_3CH3​−C(Br)(CH3​)−CH2​−CH3​

    This is named:

    2-bromo-2-methylbutane\text{2-bromo-2-methylbutane}2-bromo-2-methylbutane

  6. Check options

    • A: 111-bromo-222-methylbutane →\rightarrow→ primary substitution, not major
    • B: 222-bromo-222-methylbutane →\rightarrow→ tertiary substitution, major product
    • C: 222-bromo-333-methylbutane →\rightarrow→ same type not corresponding to the major tertiary substitution here
    • D: 111-bromo-333-methylbutane →\rightarrow→ not the major product
  7. Final answer

    The main product is:

    2-bromo-2-methylbutane\boxed{\text{2-bromo-2-methylbutane}}2-bromo-2-methylbutane​

    So the correct option is B.

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