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?

  • AB(OH)3
  • BHNO2
  • CHCO23
  • DHNO3
  • EB(OH)4

Q2:

Acetonitrile contains one CC single bond and one CN triple bond.

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

  • Asp and p
  • Bsp and sp
  • Csp and sp
  • Dsp and sp
  • Ep and p

Which orbital of the C atom contributes to the CN𝜎 bond?

  • Asp
  • Bsp
  • Cp
  • Ds
  • Esp

Which orbitals of the C atom contribute to the CN𝜋 bonds?

  • Asp
  • Bsp
  • Csp
  • Dp
  • Es

Q3:

Which of the following sets of carbon atoms cannot produce a neutral molecule with the molecular formula CH810? Note that the molecule may contain rings.

  • ATwo sp3 atoms and six sp2 atoms
  • BFour sp3 atoms, two sp2 atoms, and two sp atoms
  • CTwo sp3 atoms, four sp2 atoms, and two sp atoms
  • DTwo sp3 atoms, two sp2 atoms, and four sp atoms
  • EFour sp3 atoms and four sp atoms

Q4:

Propene, ethene, and methane can be produced by the thermal cracking of propane, as shown. 2CH()CH()+CH()+CH()+H()38362442ggggg

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

Q5:

Which of the following is the reason why the concept of hybridization is required in valence bond theory?

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

  • ANH3
  • BAlH3
  • CHO2
  • DPH3
  • EBH26

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?

  • AAluminum trichloride
  • BSulfur trioxide
  • CSulfite
  • DNitrate
  • ECarbonate

Q8:

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

CHCCHHHCCHHCHHHSCOOCCNHHHHHNHCHO

What is the hybridization of the S atoms?

  • Asp3d
  • Bsp3
  • Csp2
  • Dsp3d2
  • Esp

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

  • Asp3d2
  • Bsp3
  • Csp
  • Dsp2
  • Esp3d

Why may the N atoms be described as sp2 hybridized?

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

Q9:

Methyl isocyanate has the shown structural formula:

CNHHHCO

The CO and two CN𝜎 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 CO bond.

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

  • Asp
  • Bsp2
  • Csp3d
  • Dsp3d2
  • Esp3

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

  • Asp3d
  • Bsp3
  • Csp
  • Dsp3d2
  • Esp2

Which axis is parallel to the p orbitals that overlap to form the CN𝜋 bond?

  • A𝑦-𝑧 diagonal
  • B𝑦
  • C𝑧
  • D𝑥-𝑧 diagonal
  • E𝑥

Which axis is parallel to the p orbitals that overlap to form the CO𝜋 bond?

  • A𝑧
  • B𝑦
  • C𝑥-𝑧 diagonal
  • D𝑦-𝑧 diagonal
  • E𝑥

Q10:

The tetrathionate anion contains two types of S atoms:

OSSOOSS2OOO

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

  • Asp2
  • Bsp3d2
  • Csp
  • Dsp3d
  • Esp3

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

  • AOctahedral
  • BTetrahedral
  • CTrigonal pyramidal
  • DSquare pyramidal
  • ESquare planar

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

  • Asp3d
  • Bsp3d2
  • Csp
  • Dsp2
  • Esp3

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

  • ASeesaw
  • BTetrahedral
  • CLinear
  • DBent
  • ET-shaped

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?

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

Q12:

The structure of the peptic ulcer treatment famotidine is shown.

dacbSNSNNH2NSNH2NH2ONH2O

Which of the marked atoms display sp2-hybridization?

  • Aa and b
  • Ba only
  • Cc only
  • Db, c, and d
  • Ea, b, and d

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