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Which of the following is true about the geometry of the glycinium cation [VISUAL]?Bonding Chemistry Question

Question

Which of the following is true about the geometry of the glycinium cation [VISUAL]?

A.

The leftmost C atom and all the atoms directly bonded to it lie in the same plane.

B.

Both C atoms and both O atoms lie in the same plane.

✓ Correct
C.

The N-C-C bond angle is 180°.

D.

The geometry around the N atom is planar.

💡 Solution & Explanation

### STEPS:

1. Analyze the geometry around the carbonyl carbon (the rightmost carbon atom): This carbon atom is bonded to three neighboring atoms: the leftmost carbon atom, a double-bonded oxygen atom, and a single-bonded oxygen atom. It has zero nonbonding lone pairs of electrons.
2. Apply VSEPR theory to the carbonyl carbon: Because this carbon has exactly three electron domains (all of which are bonding domains), it exhibits a trigonal planar molecular geometry with sp2sp^2 hybridization.
3. Determine coplanarity based on trigonal planar geometry: According to VSEPR theory, all four atoms in a trigonal planar arrangement lie in the same flat plane. Therefore, the carbonyl carbon, the other carbon atom, and both oxygen atoms are coplanar, meaning both C\text{C} atoms and both O\text{O} atoms lie in the same plane. This makes Option B the correct statement.
4. Evaluate the geometry of other central atoms in the cation:
* Leftmost carbon atom (α\alpha-carbon): This carbon is single-bonded to four atoms (N\text{N}, two H\text{H}'s, and the carbonyl C\text{C}) with no nonbonding lone pairs. It has four electron domains, meaning the geometry around it is roughly tetrahedral.
* Nitrogen atom: The nitrogen atom is bonded to four atoms (three H\text{H}'s and the leftmost C\text{C}) with no nonbonding lone pairs, giving it four electron domains. The geometry of the electron domains around the nitrogen atom is roughly tetrahedral.

*

### WHY_OTHERS_WRONG:

  • Option A is incorrect: The leftmost carbon atom is bonded to four atoms and has four electron domains, giving it a three-dimensional tetrahedral molecular geometry rather than a planar one. Thus, the atoms bonded to it do not all lie in the same plane.
  • Option C is incorrect: Because the leftmost carbon atom has tetrahedral geometry, the N-C-C\text{N-C-C} bond angle is roughly 109109^\circ, which is significantly bent compared to a linear 180180^\circ angle.
  • Option D is incorrect: The nitrogen atom is bonded to four atoms and has four electron domains, giving it a three-dimensional tetrahedral geometry rather than a planar one.
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