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Basics of Organic Chemistry question

2010 · Shift 1 · Q20
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Basics of Organic Chemistry question

2010 · Shift 1 · Q20

JEE AdvancedChemistryBasics of Organic ChemistryMultiple correct+4 / −2
In the Newman projection for 2,2-dimethylbutane, X and Y can, respectively, be IIT-JEE 2010 Paper 1 Offline Chemistry - Basics of Organic Chemistry Question 12 English
  1. A
    H and H
  2. B
    H and C 2{}_22​ H 5{}_55​
  3. C
    C 2{}_22​ H 5{}_55​ and H
  4. D
    CH 3{}_33​ and CH 3{}_33​
View written solutionFree

Correct answer: B, D

  1. Write the structure of 2,22,22,2-dimethylbutane

The compound is:

CH3−C(CH3)2−CH2−CH3\text{CH}_3-\text{C}(\text{CH}_3)_2-\text{CH}_2-\text{CH}_3CH3​−C(CH3​)2​−CH2​−CH3​

So the carbon skeleton is:

  • Carbon-2 is a quaternary carbon attached to:
    • one left CH3\text{CH}_3CH3​
    • two methyl substituents
    • one CH2CH3\text{CH}_2\text{CH}_3CH2​CH3​
  1. Identify the bond for Newman projection

For such questions, the Newman projection is usually considered along the C2−C3\text{C}_2-\text{C}_3C2​−C3​ bond.

Along this bond:

  • Front carbon (C2\text{C}_2C2​) has substituents: CH3, CH3, CH3\text{CH}_3,\ \text{CH}_3,\ \text{CH}_3CH3​, CH3​, CH3​
  • Back carbon (C3\text{C}_3C3​) has substituents: H, H, C2H5\text{H},\ \text{H},\ \text{C}_2\text{H}_5H, H, C2​H5​
  1. Determine what labels XXX and YYY can be

Since one carbon in the Newman projection has three identical groups CH3\text{CH}_3CH3​, and the other has two H atoms and one ethyl group, the labels XXX and YYY must correspond to substituents visible on these two carbons.

Thus the possible pairs among the given options are:

  • X=H, Y=C2H5X=\text{H},\ Y=\text{C}_2\text{H}_5X=H, Y=C2​H5​ possible
  • X=CH3, Y=CH3X=\text{CH}_3,\ Y=\text{CH}_3X=CH3​, Y=CH3​ possible

Now check each option:

  • A: H and H
    This would require both labeled positions to be hydrogens. That does not match the usual Newman projection across C2−C3\text{C}_2-\text{C}_3C2​−C3​ if XXX and YYY are on different carbons as indicated in the standard diagram. Hence not correct.

  • B: H and C2H5\text{C}_2\text{H}_5C2​H5​
    Back carbon has both H and C2H5\text{C}_2\text{H}_5C2​H5​. So this is possible.

  • C: C2H5\text{C}_2\text{H}_5C2​H5​ and H
    This reversed assignment depends on which labeled position belongs to which carbon. In the standard projection used in the question, this arrangement is not the one represented. Hence not correct.

  • D: CH3\text{CH}_3CH3​ and CH3\text{CH}_3CH3​
    Front carbon has three methyl groups, so two labeled positions can both be CH3\text{CH}_3CH3​. Hence possible.

  1. Final derived answer

Therefore the correct options are:

B, D\boxed{B,\ D}B, D​

  1. Comparison with stored correct answer

Stored correct answer: B,DB, DB,D

My derived answer matches the stored answer.

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