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Hydrocarbons question

2003 · Shift 0 · Q14
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Hydrocarbons question

2003 · Shift 0 · Q14

JEE MainChemistryHydrocarbonsMCQ+4 / −1
On mixing a certain alkane with chlorine and irradiating it with ultravioletlight, it forms only one monochloroalkane. This alkane could be
  1. A
    pentane
  2. B
    isopentane
  3. C
    neopentane
  4. D
    propane
View written solutionFree

Correct answer: C

  1. Concept used: monochlorination of alkanes

    On chlorination in ultraviolet light, one hydrogen atom of the alkane is replaced by chlorine: R-H+Cl2→hνR-Cl+HCl\text{R-H} + \text{Cl}_2 \xrightarrow{h\nu} \text{R-Cl} + \text{HCl}R-H+Cl2​hν​R-Cl+HCl

    If an alkane gives only one monochloroalkane, then all hydrogen atoms must be equivalent by symmetry.

  2. Check each option

    Option A: pentane, CH3−CH2−CH2−CH2−CH3\mathrm{CH_3-CH_2-CH_2-CH_2-CH_3}CH3​−CH2​−CH2​−CH2​−CH3​

    Pentane has three different types of hydrogens:

    • terminal CH3\mathrm{CH_3}CH3​ hydrogens
    • next CH2\mathrm{CH_2}CH2​ hydrogens
    • middle CH2\mathrm{CH_2}CH2​ hydrogens

    So monochlorination can occur at different positions, giving more than one monochloro product.

    Hence, A is not correct.


    Option B: isopentane (2-methylbutane)

    Structure: CH3−CH(CH3)−CH2−CH3\mathrm{CH_3-CH(CH_3)-CH_2-CH_3}CH3​−CH(CH3​)−CH2​−CH3​

    It has multiple non-equivalent hydrogens:

    • tertiary hydrogen on the second carbon
    • secondary hydrogens on CH2\mathrm{CH_2}CH2​
    • primary hydrogens on different CH3\mathrm{CH_3}CH3​ groups

    Therefore, it gives more than one monochloroalkane.

    Hence, B is not correct.


    Option C: neopentane (2,2-dimethylpropane)

    Structure: C(CH3)4\mathrm{C(CH_3)_4}C(CH3​)4​

    In neopentane, all four methyl groups are identical due to high symmetry. Therefore, all 12 hydrogens are equivalent.

    Replacing any one hydrogen by chlorine gives the same product.

    Hence, C is correct.


    Option D: propane, CH3−CH2−CH3\mathrm{CH_3-CH_2-CH_3}CH3​−CH2​−CH3​

    Propane has two types of hydrogens:

    • primary hydrogens on terminal CH3\mathrm{CH_3}CH3​ groups
    • secondary hydrogens on middle CH2\mathrm{CH_2}CH2​ group

    So it gives two monochloro products:

    • 1-chloropropane
    • 2-chloropropane

    Hence, D is not correct.

  3. Final conclusion

    The alkane that forms only one monochloroalkane is: neopentane\boxed{\text{neopentane}}neopentane​

    So the correct option is: C\boxed{\text{C}}C​

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