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Hydrocarbons question

2025 · 22 Jan · Shift 2 · Q15
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Hydrocarbons question

2025 · 22 Jan · Shift 2 · Q15

JEE MainChemistryHydrocarbonsMCQ+4 / −1
The alkane from below having two secondary hydrogens is :
  1. A
    2,2,4,5-Tetramethylheptane
  2. B
    2,2,4,4-Tetramethylhexane
  3. C
    4-Ethyl-3,4-dimethyloctane
  4. D
    2,2,3,3-Tetramethylpentane
View written solutionFree

Correct answer: D

  1. Key idea: secondary hydrogen

A secondary hydrogen is a hydrogen attached to a secondary carbon, i.e. a carbon bonded to two other carbons.

So we must find the alkane which has exactly two hydrogens on secondary carbons.


  1. Check each option

Option A: 2,2,4,52,2,4,52,2,4,5-Tetramethylheptane

Write the main chain of heptane:

C1−C2−C3−C4−C5−C6−C7C_1-C_2-C_3-C_4-C_5-C_6-C_7C1​−C2​−C3​−C4​−C5​−C6​−C7​

Substituents:

  • at C2C_2C2​: two methyl groups
  • at C4C_4C4​: one methyl group
  • at C5C_5C5​: one methyl group

Now determine the type of each main-chain carbon:

  • C1,C7C_1, C_7C1​,C7​: primary
  • C2C_2C2​: bonded to C1,C3C_1, C_3C1​,C3​, and two methyl groups ⇒\Rightarrow⇒ quaternary
  • C3C_3C3​: bonded to C2C_2C2​ and C4C_4C4​ ⇒\Rightarrow⇒ secondary, so it has 2 secondary H
  • C4C_4C4​: bonded to C3,C5C_3, C_5C3​,C5​, and one methyl group ⇒\Rightarrow⇒ tertiary, so 1 tertiary H
  • C5C_5C5​: bonded to C4,C6C_4, C_6C4​,C6​, and one methyl group ⇒\Rightarrow⇒ tertiary, so 1 tertiary H
  • C6C_6C6​: bonded to C5C_5C5​ and C7C_7C7​ ⇒\Rightarrow⇒ secondary, so it has 2 secondary H

Total secondary hydrogens =2+2=4=2+2=4=2+2=4.

So, Option A is not correct.


Option B: 2,2,4,42,2,4,42,2,4,4-Tetramethylhexane

Main chain:

C1−C2−C3−C4−C5−C6C_1-C_2-C_3-C_4-C_5-C_6C1​−C2​−C3​−C4​−C5​−C6​

Substituents:

  • at C2C_2C2​: two methyl groups
  • at C4C_4C4​: two methyl groups

Carbon types:

  • C2C_2C2​: quaternary
  • C4C_4C4​: quaternary
  • C3C_3C3​: bonded to C2C_2C2​ and C4C_4C4​ only ⇒\Rightarrow⇒ secondary, so it has 2 secondary H
  • C1,C5,C6C_1, C_5, C_6C1​,C5​,C6​ and all methyl substituent carbons are primary except C5C_5C5​ is bonded to C4C_4C4​ and C6C_6C6​, so actually C5C_5C5​ is secondary

Let us correct that carefully:

  • C1C_1C1​: primary
  • C2C_2C2​: quaternary
  • C3C_3C3​: secondary ⇒2\Rightarrow 2⇒2 secondary H
  • C4C_4C4​: quaternary
  • C5C_5C5​: bonded to C4C_4C4​ and C6C_6C6​ ⇒\Rightarrow⇒ secondary ⇒2\Rightarrow 2⇒2 secondary H
  • C6C_6C6​: primary

Total secondary hydrogens =2+2=4=2+2=4=2+2=4.

So, Option B is not correct.


Option C: 444-Ethyl-3,43,43,4-dimethyloctane

Main chain:

C1−C2−C3−C4−C5−C6−C7−C8C_1-C_2-C_3-C_4-C_5-C_6-C_7-C_8C1​−C2​−C3​−C4​−C5​−C6​−C7​−C8​

Substituents:

  • at C3C_3C3​: one methyl
  • at C4C_4C4​: one methyl and one ethyl

Carbon types:

  • C3C_3C3​: bonded to C2,C4C_2, C_4C2​,C4​, and methyl ⇒\Rightarrow⇒ tertiary
  • C4C_4C4​: bonded to C3,C5C_3, C_5C3​,C5​, methyl, ethyl ⇒\Rightarrow⇒ quaternary
  • C2C_2C2​: secondary ⇒2\Rightarrow 2⇒2 secondary H
  • C5C_5C5​: secondary ⇒2\Rightarrow 2⇒2 secondary H
  • C6C_6C6​: secondary ⇒2\Rightarrow 2⇒2 secondary H
  • C7C_7C7​: secondary ⇒2\Rightarrow 2⇒2 secondary H
  • in the ethyl substituent, the carbon attached to C4C_4C4​ is also secondary? No — it is bonded to C4C_4C4​ and terminal CH3CH_3CH3​, so yes, that carbon is secondary ⇒2\Rightarrow 2⇒2 secondary H

Thus total secondary hydrogens are much more than 2.

So, Option C is not correct.


Option D: 2,2,3,32,2,3,32,2,3,3-Tetramethylpentane

Main chain:

C1−C2−C3−C4−C5C_1-C_2-C_3-C_4-C_5C1​−C2​−C3​−C4​−C5​

Substituents:

  • at C2C_2C2​: two methyl groups
  • at C3C_3C3​: two methyl groups

Carbon types:

  • C2C_2C2​: bonded to C1,C3C_1, C_3C1​,C3​, and two methyl groups ⇒\Rightarrow⇒ quaternary
  • C3C_3C3​: bonded to C2,C4C_2, C_4C2​,C4​, and two methyl groups ⇒\Rightarrow⇒ quaternary
  • C4C_4C4​: bonded to C3C_3C3​ and C5C_5C5​ only ⇒\Rightarrow⇒ secondary, so it has 2 secondary H
  • C1,C5C_1, C_5C1​,C5​, and all methyl substituent carbons are primary

Therefore total secondary hydrogens =2=2=2.

So, Option D is correct.


  1. Final answer

The alkane having exactly two secondary hydrogens is:

D: 2,2,3,3-Tetramethylpentane\boxed{\text{D: }2,2,3,3\text{-Tetramethylpentane}}D: 2,2,3,3-Tetramethylpentane​


  1. Comparison with stored correct answer

Stored correct answer: D

My derived answer: D

Hence, they agree.

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