Challenge Questions:
Chapter 1:
1) Assign formal charges to all atoms.
2)
Draw the dipole moment for the following molecules.
3) Assign the hybridization for all non-H atoms.
4) Draw an atomic orbital energy diagram for a sp2 hybridized oxygen atom.
Chapter 2
5) Draw Line bond structures for the following molecules:
6) Draw all resonance structures for the following molecules:
Chapter 3
7) For the following questions decide which of the two hydrogens labeled in red is more acidic and
explain why you made that choice. *Note, “it had the lower pKa” is not an acceptable answer.
We will go over the answers next week at recitation.
Chapter 4
8) For the following substituted cyclohexane rings please draw all possible chair conformations and
then indicate which chair is the most stable. Also, explain your choice using a Newman
projection of each chair.
Chapter 5
9) For the following molecule please do the following:
1) Circle all stereocenters
2) Assign the absolute stereochemical configuration (R or S) of each stereocenter
Chapter 7
10) For the following reactions label which molecules are the electrophile, nucleophile, and leaving
group
11) For the following pairs of nucleophiles determine which is the stronger nucleophile
12) Draw the reaction scheme and predict the products of the reactions drawn below.
a) Treatment of (R)-2-bromo-7-methyloctane with NaCN in DMSO.
b) Treatment of (R)-3,3-dimethyloctan-2-ol with H2SO4 and MeOH.
Chapter 8
13) Draw the elimination products of the following reactions.
14) Draw the major products of the following elimination reactions and assign the stereochemistry
of all stereogenic centers in both starting materials and products.
Chapter 9
15) Draw the missing component of each reaction. This could be starting materials, or major
products.
16) Propose a “multi-step” synthesis to convert the starting material below to the desired product.
This will take more than one step.
17) For the following problems propose a “multi-step” synthesis to convert the starting material
below to the desired product. This will take more than one step.
18) Treatment of an alkene with HCl typically yields a hydrochlorination product. However,
treatment of the linear alkene drawn below with HCl yields cyclic product that does not contain
a chlorine atom.
a. Draw the mystery cyclic product.
b. Provide a curved arrow mechanism for its formation
c. Comment on the stereochemical outcome of the reaction. Will there be diastereomers?
Enantiomers? If so, please provide a reason.
Chapter 10
19) For the following problems propose a “multi-step” synthesis to convert the starting material
below to the desired product. This will take more than one step.
Chapter 11
20) For the following problems propose a “multi-step” synthesis to convert the starting material
below to the desired product. This will take more than one step.
ANSWER KEY
Chapter 1.
1)
2)
3)
4)
Chapter 2
5)
6)
Chapter 3
7)
Chapter 4
8)
1)
2)
3)
4)
5)
Chapter 5
9)
Chapter 7
10)
11)
12)
Chapter 8
13)
14)
Chapter 9
15)
16)
17)
18)
a.
b.
c. The resulting product would be a mixture of diastereomers. The one stereocenter that
is present in the starting material will be unchanged as a result of the process. But the
newly formed stereocenter will be a mixture of both (R) and (S) due to the fact that the
ring closes via carbocationic intermediate.
Chapter 10
19)
Chapter 11
20)