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Haloalkanes and Haloarenes question

2025 · 22 Jan · Shift 2 · Q14
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Haloalkanes and Haloarenes question

2025 · 22 Jan · Shift 2 · Q14

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
JEE Main 2025 (Online) 22nd January Evening Shift Chemistry - Haloalkanes and Haloarenes Question 16 English The maximum number of RBr producing 2-methylbutane by above sequence of reactions is ‾\underline{\hspace{2cm}}​ . (Consider the structural isomers only)
  1. A
    5
  2. B
    3
  3. C
    4
  4. D
    1
View written solutionFree

Correct answer: C

  1. The phrase “by above sequence of reactions” in this haloalkanes context typically refers to the Wurtz reaction:

2RBr+2Na→dry etherR−R+2NaBr2RBr + 2Na \xrightarrow[\text{dry ether}]{} R-R + 2NaBr2RBr+2Nadry ether​R−R+2NaBr

So we need to find how many different structural isomers of alkyl bromides, RBrRBrRBr, can give 2-methylbutane on coupling.


  1. Target hydrocarbon:

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​

In Wurtz reaction using only one kind of alkyl bromide RBrRBrRBr, the product is:

R−RR-RR−R

Hence the target alkane must be splittable into two identical alkyl fragments.


  1. Let us check whether 2-methylbutane can be written as R−RR-RR−R for some alkyl group RRR.

2-methylbutane has 5 carbons. If it were formed as R−RR-RR−R, total carbons would be:

2×(number of carbons in R)=52 \times (\text{number of carbons in } R) = 52×(number of carbons in R)=5

This is impossible, since 5 is odd.

So one single alkyl bromide cannot give 2-methylbutane by self-coupling.


  1. Therefore, the only way to get 2-methylbutane in Wurtz reaction is by cross coupling of two different alkyl bromides:

RBr+R′Br+2Na→R−R′+2NaBrRBr + R'Br + 2Na \to R-R' + 2NaBrRBr+R′Br+2Na→R−R′+2NaBr

Now split 2-methylbutane across each C–C bond and see which pair of alkyl bromides can form it.

Structure with labels:

CH3−CH(CH3)−CH2−CH3CH_3-CH(CH_3)-CH_2-CH_3CH3​−CH(CH3​)−CH2​−CH3​

There are 4 C–C bonds to consider effectively as distinct cuts:

Cut 1: between terminal CH3CH_3CH3​ and CHCHCH

Fragments:

  • CH3⋅CH_3\cdotCH3​⋅ = methyl
  • ⋅CH(CH3)−CH2−CH3\cdot CH(CH_3)-CH_2-CH_3⋅CH(CH3​)−CH2​−CH3​ = sec-butyl

This gives bromides:

  • CH3BrCH_3BrCH3​Br (bromomethane)
  • CH3CH(Br)CH2CH3CH_3CH(Br)CH_2CH_3CH3​CH(Br)CH2​CH3​ (2-bromobutane)

Cut 2: between CHCHCH and CH2CH_2CH2​

Fragments:

  • (CH3)2CH⋅(CH_3)_2CH\cdot(CH3​)2​CH⋅ = isopropyl
  • ⋅CH2CH3\cdot CH_2CH_3⋅CH2​CH3​ = ethyl

This gives bromides:

  • (CH3)2CHBr(CH_3)_2CHBr(CH3​)2​CHBr (2-bromopropane)
  • CH3CH2BrCH_3CH_2BrCH3​CH2​Br (bromoethane)

Cut 3: between branched CH3CH_3CH3​ and central CHCHCH

This is equivalent to Cut 1, again giving:

  • methyl + sec-butyl

So no new bromides.


  1. Collect all distinct structural isomers of RBrRBrRBr involved:

  2. CH3BrCH_3BrCH3​Br

  3. CH3CH(Br)CH2CH3CH_3CH(Br)CH_2CH_3CH3​CH(Br)CH2​CH3​ (2-bromobutane)

  4. CH3CH2BrCH_3CH_2BrCH3​CH2​Br (bromoethane)

  5. (CH3)2CHBr(CH_3)_2CHBr(CH3​)2​CHBr (2-bromopropane)

Thus, the maximum number of distinct structural isomeric alkyl bromides that can produce 2-methylbutane is:

444


  1. Therefore the correct option is:

4\boxed{4}4​

which corresponds to Option C.

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