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Hydrocarbons question

2012 · Shift 0 · Q4
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Hydrocarbons question

2012 · Shift 0 · Q4

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of mono substituted alkyl halide ?
  1. A
    Tertiary butyl chloride
  2. B
    Neopentane
  3. C
    Isohexane
  4. D
    Neohexane
View written solutionFree

Correct answer: B

  1. Find the hydrocarbon with molecular mass 72u72u72u

For an alkane, general formula is: CnH2n+2C_nH_{2n+2}Cn​H2n+2​ Its molecular mass is: 12n+(2n+2)=14n+212n + (2n+2) = 14n+212n+(2n+2)=14n+2 Given: 14n+2=7214n+2=7214n+2=72 14n=7014n=7014n=70 n=5n=5n=5 So the hydrocarbon is: C5H12C_5H_{12}C5​H12​

  1. Write the isomers of C5H12C_5H_{12}C5​H12​

The structural isomers are:

  • nnn-pentane
  • isopentane (222-methylbutane)
  • neopentane (2,22,22,2-dimethylpropane)

The question asks for the branched chain isomer that gives only one isomer of monosubstituted alkyl halide.

  1. Check each branched isomer

(i) Isopentane: 222-methylbutane

Structure: CH3−CH(CH3)−CH2−CH3CH_3-CH(CH_3)-CH_2-CH_3CH3​−CH(CH3​)−CH2​−CH3​ Here, hydrogen atoms are not all equivalent. There are different types of carbon atoms, so substitution of one H by halogen can occur at different positions.

Thus, isopentane gives more than one monosubstituted alkyl halide.

(ii) Neopentane: 2,22,22,2-dimethylpropane

Structure: C(CH3)4C(CH_3)_4C(CH3​)4​ All four methyl groups are equivalent due to symmetry. Therefore, all 121212 hydrogens are equivalent.

So replacing any one H by halogen gives the same single product.

Hence, neopentane gives only one monosubstituted alkyl halide.

  1. Evaluate options
  • A: Tertiary butyl chloride o oo not a hydrocarbon, already a haloalkane, so not relevant.
  • B: Neopentane o oo correct.
  • C: Isohexane o oo formula is not C5H12C_5H_{12}C5​H12​.
  • D: Neohexane o oo formula is not C5H12C_5H_{12}C5​H12​.
  1. Final answer

The required branched chain isomer is: Neopentane\boxed{\text{Neopentane}}Neopentane​

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