- A2,2,4,5-Tetramethylheptane
- B2,2,4,4-Tetramethylhexane
- C4-Ethyl-3,4-dimethyloctane
- D2,2,3,3-Tetramethylpentane
View written solutionFree
Correct answer: D
- 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.
- Check each option
Option A: -Tetramethylheptane
Write the main chain of heptane:
Substituents:
- at : two methyl groups
- at : one methyl group
- at : one methyl group
Now determine the type of each main-chain carbon:
- : primary
- : bonded to , and two methyl groups quaternary
- : bonded to and secondary, so it has 2 secondary H
- : bonded to , and one methyl group tertiary, so 1 tertiary H
- : bonded to , and one methyl group tertiary, so 1 tertiary H
- : bonded to and secondary, so it has 2 secondary H
Total secondary hydrogens .
So, Option A is not correct.
Option B: -Tetramethylhexane
Main chain:
Substituents:
- at : two methyl groups
- at : two methyl groups
Carbon types:
- : quaternary
- : quaternary
- : bonded to and only secondary, so it has 2 secondary H
- and all methyl substituent carbons are primary except is bonded to and , so actually is secondary
Let us correct that carefully:
- : primary
- : quaternary
- : secondary secondary H
- : quaternary
- : bonded to and secondary secondary H
- : primary
Total secondary hydrogens .
So, Option B is not correct.
Option C: -Ethyl--dimethyloctane
Main chain:
Substituents:
- at : one methyl
- at : one methyl and one ethyl
Carbon types:
- : bonded to , and methyl tertiary
- : bonded to , methyl, ethyl quaternary
- : secondary secondary H
- : secondary secondary H
- : secondary secondary H
- : secondary secondary H
- in the ethyl substituent, the carbon attached to is also secondary? No — it is bonded to and terminal , so yes, that carbon is secondary secondary H
Thus total secondary hydrogens are much more than 2.
So, Option C is not correct.
Option D: -Tetramethylpentane
Main chain:
Substituents:
- at : two methyl groups
- at : two methyl groups
Carbon types:
- : bonded to , and two methyl groups quaternary
- : bonded to , and two methyl groups quaternary
- : bonded to and only secondary, so it has 2 secondary H
- , and all methyl substituent carbons are primary
Therefore total secondary hydrogens .
So, Option D is correct.
- Final answer
The alkane having exactly two secondary hydrogens is:
- Comparison with stored correct answer
Stored correct answer: D
My derived answer: D
Hence, they agree.
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