Lesson 18
CHEM 232: Lesson 19
Elimination
at sp3 Carbons
SOLUTIONS
Elimination
at sp3
Discussion Problems
2
1
3
Largest heat of hydrogenation
How many distinct alkene products are
possible when the al
Lesson 08
Linear
Combinations of
Atomic Orbitals
SOLUTIONS
As two separated hydrogen atoms approach bonding distance with one another,
what happens to the electron density around each atom and why?
El
Lesson 3
Functional Groups
SOLUTIONS
For each highlighted atom, identify its connectivity, number of EPDs, geometry, and
likely hybridization state.
Draw the best Lewis structure for CH3CHO, a neutral
Lesson 9
Molecular
Orbital Theory
SOLUTIONS
LCAO Tool: 2s + 2s
LCAO Tool: 2py 2py
Which of the molecular orbitals
shown possess pi-type symmetry?
B, C, F
Which possess two angular nodes?
C, D
SHEET #1
Lesson 10
Hybrid Atomic
Orbitals
SOLUTIONS
Discussion Problem
Match the numbers associated with the energy diagrams in
Figure 1 to the corresponding structure. NOTE: These are
partial MO diagrams for
Lesson 11
Frontier Orbital
Interactions
SOLUTIONS
Discussion Problems (resonance)
frontier orbitals?
Draw curved arrows to show the flow of
electrons from the one
resonance
contributor to the next. In
Lesson 12
Conformers
SOLUTIONS
Select the Newman projection that corresponds to the sawhorse projection shown.
Convert this sawhorse projection to a line-angle drawing with correct
stereochemistry.
Dr
Lesson 4
Models and Lingo
SOLUTIONS
Discussion Problems
Draw the structure of an alkane that has eight carbons and only
tertiary hydrogens.
Demerol, an opioid analgesic is shown. What kind of function
Lesson 7
Resonance
SOLUTIONS
Flowcharts
Discussion Problem
Is acetamide a stronger or weaker base than trimethylamine?
The positive charge on the nitrogen in the molecule shown can be delocalized over
Lesson 2
Building Blocks
SOLUTIONS
www.youtube.com/watch?v=Uy0m7jnyv6U
Formal Charges Range from -1 to +1
B
C
N
O
F
Assign formal charge to the building blocks shown above. Formal charges of periodtwo
Lesson 1
Period 2 Elements
SOLUTIONS
Counting Electrons
How many valence electrons are in a molecule
with formula:
C4H7FO
C6H8N+
C6H7P
How many total electrons are in trinitramide?
Counting EPDs
Lesson 5
Symmetry and Isomers
SOLUTIONS
Identify Rotational Axes
1 perpendicular
to plane of page
1
3 (1 perpendicular
to plane of page)
Identify Mirror Planes
1
3 (1 in plane of page)
Identify Invers
Lesson 15
Structure &
Reactivity
SOLUTIONS
Discussion Problems
H+ + F(g)
H+ + I(g)
HF
(g)
HI
(g)
H+ + F(aq)
H+ + I(aq)
HF
HF
Solvation
X
X
X
Larger in the sense of magnitude. Solvation of the ions is
Lesson 17
Substitution
at sp3 Carbons
SOLUTIONS
Discussion Problems
Discussion Problems
(6) Is the methoxide anion more reactive in methanol or dimethyl sulfoxide? Why?
Methoxide is more reactive in D
Lesson 16
Acid-Base
Equilibria
SOLUTIONS
Discussion Problem
Why is methylamine a better base than methanol?
Why is methanol a better acid than methylamine?
An important contributor to the stability of
Lesson 19
Stereochemistry of
Substitution and Elimination
SOLUTIONS
Draw the major substitution and elimination products arising from the reaction
conditions shown.
Draw the major substitution and eli
Lesson 20
Carbocation
Rearrangements
SOLUTIONS
Discussion Problems
A Note re: POTD Mechanism
Questions
The following slides include solutions to some
of the POTD mechanism questions.
It is not suffi
Lesson 21
Leaving Groups,
Nucleophiles, and
Ring-Opening
SOLUTIONS
p-Toluenesulfonate (TsO-) is one of the most common sulfonate esters
employed in practice. Draw the mechanism for the formation of Et
Lesson 14
Understanding
Reactivity
SOLUTIONS
Identify Frontier Orbitals
Identify Frontier Orbitals
Insert arrows for the given reaction. Given that this is an exothermic reaction, draw
the reaction co
Lesson 6
Chirality and
Stereocenters
SOLUTIONS
Select all of the CHIRAL molecules from those shown.
Identify all of the stereogenic sp3-hybridized atoms in this compound.
Discussion Problems
Complete