Unformatted text preview: toms; the two carbons that are not sp2 hybridized are sp3 hybridized, and the
oxygens marked with angles a and c are sp3 hybridized.
e. Yes, the π electrons in the ring are delocalized. The atoms in the ring are all sp2
hybridized. This leaves a p orbital perpendicular to the plane of the ring from each atom.
Overlap of all six of these p orbitals results in a π molecular orbital system where the
electrons are delocalized above and below the plane of the ring (similar to benzene in
Figure 14.50 of the text).
The three C atoms each bonded to three H atoms are sp3 hybridized (tetrahedral geometry);
the other five C atoms with trigonal planar geometry are sp2 hybridized. The one N atom with
the double bond is sp2 hybridized, and the other three N atoms are sp3 hybridized. The
answers to the questions are: •
• 6 total C and N atoms are sp2 hybridized
6 total C and N atoms are sp3 hybridized
0 C and N atoms are sp hybridized (linear geometry)
25 σ bonds and 4 π bonds CHAP. 14
593 72. COVALENT BONDING: ORBITALS - EVEN-NUMBER PROBLEMS We rotated the molecule about some single bonds from the structure given in the question.
Following the bonding guidelines outlined in the answer to Exercise 14.70, a Lewis structure
for aspartame is: H
O H C H O C C H O C H H N C C N C C H H H H O H H H H H C O C C C
C C H H H Another resonance structure could be drawn having the double bonds in the benzene ring
moved over one position.
Atoms that have trigonal planar geometry of electron pairs are assumed to have sp2
hybridization, and atoms with tetrahedral geometry of electron pairs are assumed to have sp3
hybridization. All the N atoms have tetrahedral geometry, so they are all sp3 hybridized (no
sp2 hybridization). The oxygens double bonded to carbon atoms are sp2 hybridized; the other
two oxygens with two single bonds are sp3 hybridized. For the carbon atoms, the six carbon
atoms in the benzene ring are sp2 hybridized, and the three carbons double bonded to oxygen
are also sp2 hybridized (tetrahedral geometry). Answering the questions: •
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