JEE Challenger
More from Organic Chemistry - Basic Principles

Identify Substituents in Newman Projection of 2,2-Dimethylbutane

In the Newman projection for 2,2-dimethylbutane

Diagram 0

X\mathbf{X} and Y\mathbf{Y} can respectively be

Options

A

H\text{H} and H\text{H}

B

H\text{H} and C2H5\text{C}_2\text{H}_5

Correct
C

C2H5\text{C}_2\text{H}_5 and H\text{H}

D

CH3\text{CH}_3 and CH3\text{CH}_3

Correct

Step-by-Step Solution

To determine the substituents X\mathbf{X} and Y\mathbf{Y} in the given Newman projection of 2,2-dimethylbutane, we analyze the molecular structure and the projection diagram.

1. Molecular Structure of 2,2-Dimethylbutane

The IUPAC structure and numbering of 2,2-dimethylbutane is:
C1H3−C2(CH3)2−C3H2−C4H3\overset{1}{\text{C}}\text{H}_3 - \overset{2}{\text{C}}(\text{CH}_3)_2 - \overset{3}{\text{C}}\text{H}_2 - \overset{4}{\text{C}}\text{H}_3

2. Analysis of the Given Newman Projection Diagram

From the visual representation:

  • Front Carbon (represented by the central vertex where three bonds meet):
    It has two hydrogen atoms (−H-\text{H}) and one substituent X\mathbf{X} attached to it. Thus, its substituents are:
    (X,H,H)(\mathbf{X}, \text{H}, \text{H})
  • Back Carbon (represented by the circle):
    It has two methyl groups (−CH3-\text{CH}_3) and one substituent Y\mathbf{Y} attached to it. Thus, its substituents are:
    (CH3,CH3,Y)(\text{CH}_3, \text{CH}_3, \mathbf{Y})

Since the back carbon has two methyl groups attached to it, it must correspond to C2\text{C}_2 of 2,2-dimethylbutane. The front carbon, being directly bonded to C2\text{C}_2, can be either C1\text{C}_1 or C3\text{C}_3.


3. Case Analysis

Case 1: Viewing along the C1−C2\text{C}_1-\text{C}_2 bond (Front Carbon = C1\text{C}_1, Back Carbon = C2\text{C}_2)

  • Front Carbon (C1\text{C}_1): Being a terminal methyl group, C1\text{C}_1 is bonded to three hydrogen atoms (−H,−H,−H-\text{H}, -\text{H}, -\text{H}).
    Comparing with (X,H,H)(\mathbf{X}, \text{H}, \text{H}), we get:
    X=H\mathbf{X} = \text{H}

  • Back Carbon (C2\text{C}_2): Apart from the C1−C2\text{C}_1-\text{C}_2 bond, C2\text{C}_2 is bonded to two methyl groups (−CH3,−CH3-\text{CH}_3, -\text{CH}_3) and an ethyl group (−CH2CH3=−C2H5-\text{CH}_2\text{CH}_3 = -\text{C}_2\text{H}_5).
    Comparing with (CH3,CH3,Y)(\text{CH}_3, \text{CH}_3, \mathbf{Y}), we get:
    Y=C2H5\mathbf{Y} = \text{C}_2\text{H}_5

Thus, X=H\mathbf{X} = \text{H} and Y=C2H5\mathbf{Y} = \text{C}_2\text{H}_5, which corresponds to Option B.


Case 2: Viewing along the C3−C2\text{C}_3-\text{C}_2 bond (Front Carbon = C3\text{C}_3, Back Carbon = C2\text{C}_2)

  • Front Carbon (C3\text{C}_3): C3\text{C}_3 is bonded to two hydrogen atoms and one methyl group (−C4H3-\text{C}_4\text{H}_3).
    Comparing with (X,H,H)(\mathbf{X}, \text{H}, \text{H}), we get:
    X=CH3\mathbf{X} = \text{CH}_3

  • Back Carbon (C2\text{C}_2): Apart from the C2−C3\text{C}_2-\text{C}_3 bond, C2\text{C}_2 is bonded to three methyl groups (two attached to C2\text{C}_2 and one from C1\text{C}_1).
    Comparing with (CH3,CH3,Y)(\text{CH}_3, \text{CH}_3, \mathbf{Y}), we get:
    Y=CH3\mathbf{Y} = \text{CH}_3

Thus, X=CH3\mathbf{X} = \text{CH}_3 and Y=CH3\mathbf{Y} = \text{CH}_3, which corresponds to Option D.


Conclusion

Therefore, X\mathbf{X} and Y\mathbf{Y} can respectively be H\text{H} and C2H5\text{C}_2\text{H}_5 or CH3\text{CH}_3 and CH3\text{CH}_3.

Correct Options: B and D