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Exercises · 8.36

Q.In the organic compound CH2=CH—CH2—CH2—C≡CH, the pair of hybridised orbitals involved in the formation of the C2—C3 bond is:

(a) sp–sp²
(b) sp–sp³
(c) sp²–sp³
(d) sp³–sp³.
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Number the carbons left to right, identify each carbon's hybridization from its bonding environment, then read off the orbital types that overlap to form the C₂—C₃ σ bond. The answer is (c) sp²–sp³.


The question asks which hybrid orbitals overlap to form a specific C—C single bond. The strategy is straightforward: determine the hybridization of each carbon atom from its bonding pattern, then identify the orbitals that meet to form the bond in question.

Understanding Hybridization from Bonding

Hybridization reflects the geometry a carbon adopts to accommodate its bonds:

  • sp: linear, forms two σ bonds (e.g., in a triple bond + one single bond)
  • sp²: trigonal planar, forms three σ bonds (e.g., in a double bond + two single bonds)
  • sp³: tetrahedral, forms four σ bonds (all single bonds)

A σ bond between two carbons forms by the head-on overlap of one hybrid orbital from each atom.


Step-by-Step Analysis

1. Number the carbon chain

Let's label the carbons from left to right as C₁ through C₆:

CX1HX2=CX2H−CX3HX2−CX4HX2−CX5≡CX6H\ce{C_1H_2=C_2H-C_3H_2-C_4H_2-C_5≡C_6H}

2. Determine the hybridization of each carbon

  • C₁: part of C=C\ce{C=C} double bond → makes three σ bonds (one to C₂, two to H) → sp²
  • C₂: part of C=C\ce{C=C} double bond → makes three σ bonds (one to C₁, one to C₃, one to H) → sp²
  • C₃: single bonds only → makes four σ bonds (one to C₂, one to C₄, two to H) → sp³
  • C₄: single bonds only → makes four σ bonds (one to C₃, one to C₅, two to H) → sp³
  • C₅: part of C≡C\ce{C≡C} triple bond → makes two σ bonds (one to C₄, one to C₆) → sp
  • C₆: part of C≡C\ce{C≡C} triple bond → makes two σ bonds (one to C₅, one to H) → sp …

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