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NCERT Exemplar · Q16

Q.Which of the following compounds contain all the carbon atoms in the same hybridisation state? (Note: more than one of the given options may be correct.)

(i) H—C≡C—C≡C—H
(ii) CH3—C≡C—CH3
(iii) CH2=C=CH2
(iv) CH2=CH—CH=CH2
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To determine the hybridization of carbon atoms, count the number of sigma bonds around each carbon. If a carbon forms 4 sigma bonds, it is sp3sp^3; 3 sigma bonds, sp2sp^2; and 2 sigma bonds, spsp. Compounds (i) and (iv) have all carbon atoms in the same hybridization state.

Understanding the hybridization state of carbon atoms is fundamental in organic chemistry, as it dictates the geometry and reactivity of molecules. For carbon, hybridization is primarily determined by the number of sigma (σ\sigma) bonds it forms. Each single bond is a sigma bond, a double bond consists of one sigma and one pi (π\pi) bond, and a triple bond consists of one sigma and two pi bonds.

The general rule for determining hybridization for a central atom (like carbon) is to calculate its steric number, which is the sum of the number of sigma bonds and the number of lone pairs around it. For carbon in stable organic compounds, there are typically no lone pairs. Therefore, the hybridization of a carbon atom simplifies to:

  • Steric Number = 4 (4 sigma bonds): The carbon atom is sp3sp^3 hybridized. This leads to a tetrahedral geometry.
  • Steric Number = 3 (3 sigma bonds): The carbon atom is sp2sp^2 hybridized. This leads to a trigonal planar geometry.
  • Steric Number = 2 (2 sigma bonds): The carbon atom is spsp hybridized. This leads to a linear geometry.

Let's apply this concept to each given compound.

  1. Analyze Option (i): H—C≡C—C≡C—H

    This compound is butadiyne. Let's label the carbon atoms from left to right as C1, C2, C3, and C4.

    • C1: Forms one C—H single bond (σ\sigma) and one C≡C triple bond (which contains one σ\sigma and two π\pi bonds). So, C1 forms a total of 1+1=21 + 1 = 2 sigma bonds. Therefore, C1 is spsp hybridized.
    • C2: Forms one C≡C triple bond to C1 (one σ\sigma) and one C≡C triple bond to C3 (one σ\sigma). So, C2 forms a total of 1+1=21 + 1 = 2 sigma bonds. Therefore, C2 is spsp hybridized.
    • C3: Forms one C≡C triple bond to C2 (one σ\sigma) and one C≡C triple bond to C4 (one σ\sigma). So, C3 forms a total of 1+1=21 + 1 = 2 sigma bonds. Therefore, C3 is spsp hybridized.
    • C4: Forms one C≡C triple bond to C3 (one σ\sigma) and one C—H single bond (σ\sigma). So, C4 forms a total of 1+1=21 + 1 = 2 sigma bonds. Therefore, C4 is spsp hybridized. All carbon atoms in H—C≡C—C≡C—H are spsp hybridized.
  2. Analyze Option (ii): CH3—C≡C—CH3

    This compound is 2-butyne. Let's label the carbon atoms from left to right as C1, C2, C3, and C4.

    • C1 (methyl group): Forms three C—H single bonds (3 σ\sigma) and one C—C single bond to C2 (1 σ\sigma). So, C1 forms a total of 3+1=43 + 1 = 4 sigma bonds. Therefore, C1 is sp3sp^3 hybridized.
    • C2: Forms one C—C single bond to C1 (1 σ\sigma) and one C≡C triple bond to C3 (which contains one σ\sigma and two π\pi bonds). So, C2 forms a total of 1+1=21 + 1 = 2 sigma bonds. Therefore, C2 is spsp hybridized.
    • C3: Forms one C≡C triple bond to C2 (one σ\sigma) and one C—C single bond to C4 (1 σ\sigma). So, C3 forms a total of 1+1=21 + 1 = 2 sigma bonds. Therefore, C3 is spsp hybridized.
    • C4 (methyl group): Forms one C—C single bond to C3 (1 σ\sigma) and three C—H single bonds (3 σ\sigma). So, C4 forms a total of 1+3=41 + 3 = 4 sigma bonds. Therefore, C4 is sp3sp^3 hybridized. The carbon atoms in CH3—C≡C—CH3 are sp3sp^3 and spsp hybridized. They are not all in the same hybridization state.
  3. Analyze Option (iii): CH2=C=CH2

    This compound is allene. Let's label the carbon atoms from left to right as C1, C2, and C3.

    • C1: Forms two C—H single bonds (2 σ\sigma) and one C=C double bond to C2 (which contains one σ\sigma and one π\pi bond). So, C1 forms a total of 2+1=32 + 1 = 3 sigma bonds. Therefore, C1 is sp2sp^2 hybridized. …

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