1.
From the list of compounds shown below, draw a box around the compound that has the
largest k(hydrate) (highest concentration of the hydrate) under equilibrium conditions.
O
H2O
+
R
R
carbonyl
O
k(hydrate) = [hydrate]
[carbonyl]
OH
R
R
hydrate
O
O
O
F
F
H
F
F
F
F
O
HO
O
F
O
O
F
F
F
F
2. Fill in the box with major organic product for the reactions shown below.
O
1. NaCN (1 equiv), H 2O
O
2. dilute HCl
O
Cl
O
O
OH
MCPBA
F
F
O
catalytic HCl
H
HO
O
3. Fill in the box with the appropriate starting material, product or reagents. For products, draw
only the major organic product (unless otherwise specified). If no reaction occurs, write no
reaction (NR) for the product. Please specify the correct stereochemistry where appropriate.
Note: H3O+ = dilute aqueous acid work-up. (60 points)
O
acetic acid
remove water
H2N
OH
O
O
K2Cr2O7
H2SO4, H2O
+
P
4. Provide a detailed electron-pushing mechanism of the reaction shown below. Be sure to
include any intermediates and relevant resonance structures.
Cl
O
H
NaCN
C
N
O
5. Provide a detailed electron-pushing mechanism of the reaction shown below. Be sure to
include any intermediates and relevant resonance structures.
NH2
O
N
H2N
NH2
catalytic acetic acid
6. A H1-NMR of the product from the following reaction is shown below. Draw the product.
Cl
O
NaOCH3
9H, singlet
3H, singlet
2H, singlet
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