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Haloalkanes and Haloarenes question

2023 · 25 Jan · Shift 2 · Q6
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Haloalkanes and Haloarenes question

2023 · 25 Jan · Shift 2 · Q6

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
The isomeric deuterated bromide with molecular formula C4H8DBr\mathrm{C_4H_8DBr}C4​H8​DBr having two chiral carbon atoms is
  1. A
    2 - Bromo - 1 - deuterobutane
  2. B
    2 - Bromo - 1 - deutero - 2 - methylpropane
  3. C
    2 - Bromo - 3 - deuterobutane
  4. D
    2 - Bromo - 2 - deuterobutane
View written solutionFree

Correct answer: C

  1. Interpret the formula and requirement

We need the isomer of formula C4H8DBr\mathrm{C_4H_8DBr}C4​H8​DBr that has two chiral carbon atoms.

A chiral carbon must be attached to four different groups.


  1. Check each option

Option A: 222-Bromo-111-deuterobutane

Structure: DCH2−CH(Br)−CH2−CH3\mathrm{DCH_2-CH(Br)-CH_2-CH_3}DCH2​−CH(Br)−CH2​−CH3​

  • Carbon-2 is attached to:
    • Br\mathrm{Br}Br
    • H\mathrm{H}H
    • CH2D\mathrm{CH_2D}CH2​D
    • CH2CH3\mathrm{CH_2CH_3}CH2​CH3​

These are four different groups, so carbon-2 is chiral.

  • Carbon-1 is CH2D\mathrm{CH_2D}CH2​D, so it has two hydrogens/deuterium arrangement as:
    • D\mathrm{D}D
    • H\mathrm{H}H
    • H\mathrm{H}H
    • bonded carbon

Since two substituents are identical (H,H\mathrm{H,H}H,H), carbon-1 is not chiral.

So option A has only one chiral carbon.


Option B: 222-Bromo-111-deutero-222-methylpropane

Structure: DCH2−C(Br)(CH3)−CH3\mathrm{DCH_2-C(Br)(CH_3)-CH_3}DCH2​−C(Br)(CH3​)−CH3​

At carbon-2, the substituents are:

  • Br\mathrm{Br}Br
  • CH2D\mathrm{CH_2D}CH2​D
  • CH3\mathrm{CH_3}CH3​
  • CH3\mathrm{CH_3}CH3​

Two groups are identical (CH3\mathrm{CH_3}CH3​ and CH3\mathrm{CH_3}CH3​), so carbon-2 is not chiral.

Carbon-1 is CH2D\mathrm{CH_2D}CH2​D, which is also not chiral.

So option B has no chiral carbon.


Option C: 222-Bromo-333-deuterobutane

Structure: CH3−CH(Br)−CH(D)−CH3\mathrm{CH_3-CH(Br)-CH(D)-CH_3}CH3​−CH(Br)−CH(D)−CH3​

  • Carbon-2 is attached to:
    • Br\mathrm{Br}Br
    • H\mathrm{H}H
    • CH3\mathrm{CH_3}CH3​
    • CH(D)CH3\mathrm{CH(D)CH_3}CH(D)CH3​

All four groups are different, so carbon-2 is chiral.

  • Carbon-3 is attached to:
    • D\mathrm{D}D
    • H\mathrm{H}H
    • CH3\mathrm{CH_3}CH3​
    • CH(Br)CH3\mathrm{CH(Br)CH_3}CH(Br)CH3​

Again, all four groups are different, so carbon-3 is also chiral.

So option C has two chiral carbons.


Option D: 222-Bromo-222-deuterobutane

Structure: CH3−C(Br)(D)−CH2−CH3\mathrm{CH_3-C(Br)(D)-CH_2-CH_3}CH3​−C(Br)(D)−CH2​−CH3​

At carbon-2, substituents are:

  • Br\mathrm{Br}Br
  • D\mathrm{D}D
  • CH3\mathrm{CH_3}CH3​
  • CH2CH3\mathrm{CH_2CH_3}CH2​CH3​

These are four different groups, so carbon-2 is chiral.

No other carbon is chiral.

So option D has only one chiral carbon.


  1. Conclusion

Only option C has two chiral carbon atoms.

Therefore, the correct answer is: C\boxed{\text{C}}C​


  1. Comparison with stored correct answer

Stored correct answer: C

My derived answer: C

They match.

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