Predict the electron domain and molecular geometries around the carbon atoms labeled "?".

Carbon 1 is double-bonded to one oxygen atom ($\text{C=O}$), single-bonded to another oxygen atom ($\text{C-OH}$), and single-bonded to Carbon 2 ($\text{C-C}_2$).

• The $\text{C=O}$ double bond counts as one electron domain.
• The $\text{C-OH}$ single bond counts as one electron domain.
• The $\text{C-C}_2$ single bond counts as one electron domain. Total electron domains = 3.

With 3 electron domains and no lone pairs on the carbon atom, the electron domain geometry is trigonal planar.

Since there are no lone pairs on the central carbon atom, the molecular geometry is the same as the electron domain geometry.
Molecular geometry = trigonal planar.

For Carbon atom 2 (the chiral center):

Carbon 2 is single-bonded to:

• A hydrogen atom ($\text{C-H}$)
• A methyl group carbon ($\text{C-CH}_3$)
• A benzene ring carbon ($\text{C-C}_{\text{phenyl}}$)
• Carbon 1 (the carboxylic acid carbon) ($\text{C-C}_1$) Total electron domains = 4.

With 4 electron domains and no lone pairs on the carbon atom, the electron domain geometry is tetrahedral.

Since there are no lone pairs on the central carbon atom, the molecular geometry is the same as the electron domain geometry.
Molecular geometry = tetrahedral.

Summary:

• Carbon 1:
  • Electron domain geometry: $\boxed{\text{Trigonal planar}}$
  • Molecular geometry: $\boxed{\text{Trigonal planar}}$
• Carbon 2:
  • Electron domain geometry: $\boxed{\text{Tetrahedral}}$
  • Molecular geometry: $\boxed{\text{Tetrahedral}}$