Worksheet: Hybridization of Main-Group Elements

In this worksheet, we will practice defining hybrid orbitals and assigning the hybridization of main-group atoms based on their electron pair geometries.

Q1:

The hybridization of the central atom ( B , C , or N ) is the same in all but one of the following molecules. In which species is the hybridization different?

  • A B ( O H ) 4
  • B H N O 2
  • C B ( O H ) 3
  • D H C O 2 3
  • E H N O 3

Q2:

Acetonitrile contains one C C single bond and one C N triple bond.

Which orbitals of the C atoms overlap to form the C C bond?

  • Ap and p
  • Bsp and sp3
  • Csp3 and sp3
  • Dsp3 and p
  • Esp2 and sp3

Which orbital of the C atom contributes to the C N 𝜎 bond?

  • Asp3
  • Bsp2
  • Cs
  • Dsp
  • Ep

Which orbitals of the C atom contribute to the C N 𝜋 bonds?

  • Asp3
  • Bs
  • Cp
  • Dsp
  • Esp2

Q3:

Which of the following sets of carbon atoms cannot produce a neutral molecule with the molecular formula C H 8 1 0 ? Note that the molecule may contain rings.

  • ATwo sp3 atoms and six sp2 atoms
  • BTwo sp3 atoms, four sp2 atoms, and two sp atoms
  • CFour sp3 atoms and four sp atoms
  • DFour sp3 atoms, two sp2 atoms, and two sp atoms
  • ETwo sp3 atoms, two sp2 atoms, and four sp atoms

Q4:

Propene, ethene, and methane can be produced by the thermal cracking of propane:

For each propane molecule, how many atoms undergo a change in hybridization during this reaction?

Q5:

Why is the concept of hybridization required in valence bond theory?

  • ATo explain the relative energies of bonding orbitals
  • BTo explain the existence of degenerate bonding orbitals
  • CTo explain the existence of nonbonding orbitals
  • DTo explain the polarity of chemical bonds
  • ETo explain the geometry of bonding orbitals

Q6:

The hybridization of the nonhydrogen atom is the same in all but one of the following molecules. In which molecule is the hybridization different?

  • A P H 3
  • B H O 2
  • C N H 3
  • D B H 2 6
  • E A l H 3

Q7:

The hybridization of the central atom is the same in all but one of the following molecules and ions. In which species is the hybridization different?

  • ASulfur trioxide
  • BAluminum trichloride
  • CCarbonate
  • DNitrate
  • ESulfite

Q8:

A molecule of biotin (vitamin B7) contains two N atoms, one S atom, and two C O double bonds:

C H C C H H H C C H H C H H H S C O O C C N H H H H H N H C H O

What is the hybridization of the S atoms?

  • Asp3d2
  • Bsp2
  • Csp3d
  • Dsp
  • Esp3

What is the hybridization of the O atom in the C O double bonds?

  • Asp2
  • Bsp
  • Csp3d2
  • Dsp3d
  • Esp3

Why may the N atoms be described as sp2 hybridized?

  • AA trigonal planar shape maximizes the separation of the lone and bonding electron pairs.
  • BThe bonds between the N atoms and the alkyl C atoms are partial double bonds.
  • CThe bonds between the N atoms and the carbonyl C atoms are partial double bonds.
  • D N atoms with three bonds are always sp2 hybridized.
  • EA trigonal planar shape minimizes strain in the five-membered ring.

Q9:

Methyl isocyanate has the shown structural formula:

C N H H H C O

The C O and two C N 𝜎 bonds lie in a single plane parallel to the 𝑥 - and 𝑦 -axes and perpendicular to the 𝑧 -axis. The 𝑥 -axis is parallel to the C O bond.

What is the hybridization of the C atom in the isocyanate group?

  • Asp3d2
  • Bsp2
  • Csp3
  • Dsp3d
  • Esp

What is the hybridization of the N atom in the isocyanate group?

  • Asp2
  • Bsp
  • Csp3
  • Dsp3d
  • Esp3d2

Which axis is parallel to the p orbitals that overlap to form the C N 𝜋 bond?

  • A 𝑧
  • B 𝑦 - 𝑧 diagonal
  • C 𝑥 - 𝑧 diagonal
  • D 𝑦
  • E 𝑥

Which axis is parallel to the p orbitals that overlap to form the C O 𝜋 bond?

  • A 𝑥
  • B 𝑦 - 𝑧 diagonal
  • C 𝑥 - 𝑧 diagonal
  • D 𝑦
  • E 𝑧

Q10:

The tetrathionate anion contains two types of S atoms:

O S S O O S S 2 O O O

What is the hybridization of the S atoms in the S O bonds?

  • A sp3
  • B sp3d2
  • C sp3d
  • D sp2
  • E sp

What term best describes the bonding geometry around the S atoms in the S O bonds?

  • AOctahedral
  • BTrigonal pyramidal
  • CSquare planar
  • DSquare pyramidal
  • ETetrahedral

What is the hybridization of the S atoms with two S S bonds?

  • Asp3d
  • Bsp3
  • Csp
  • Dsp2
  • Esp3d2

What term best describes the bonding geometry around the S atoms with two S S bonds?

  • ALinear
  • BTetrahedral
  • CBent
  • DT-shaped
  • ESeesaw

Q11:

Nitrogen and phosphorus are group 15 elements, but nitrogen forms only three bonds, while phosphorus can form up to five. What accounts for the ability of phosphorus to form more bonds?

  • APhosphorus is more electronegative than nitrogen.
  • BNitrogen has three unpaired electrons in its ground state.
  • CPhosphorus has two more valence electrons than nitrogen.
  • DPhosphorus has an additional electron shell.

Q12:

The structure of the peptic ulcer treatment famotidine is shown.

d a c b S N S N N H 2 N S N H 2 N H 2 O N H 2 O

Which of the marked atoms display sp2-hybridization?

  • Aa, b, and d
  • Ba only
  • Cb, c, and d
  • Da and b
  • Ec only

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