Chemistry 202-102
Test # 1
Dr. Richard Rogers
February 2, 2010
Name: ___________________________________________
1. In the following reactions, label each reactant as either an acid or a base (5 points)
2 Na 2 HPO 4
+
Na 2CO 3
N
AlCl3 +
O
O
H
+
Na 3 PO 4 + H 2 O + CO 2
N
Cl
Al Cl
Cl
O H
Cl
HCl
O
O
O
HI
H
O
+
H
+
O
NH3
NH4
O
O H
I
1
2. In the following reactions, label each reactant as either an electrophile or a nucleophile.
Circle the actual electrophilic or nucleophilic element in each reactant (9 points).
+
CH3 Li
O-Li+
O
CH3OH
+
PhCH2I
H
Cl
CH4
CH3O Li
PhCH2OCH2CH3
O
N
+
+
CH3
H 3C
N
+
HCl
3a. In the molecule shown below (3b), how many peaks will appear in the decoupled 13C
nmr spectra (4 points)?
3b. In the boxes, show the number of peaks that will appear for the protons attached to
the indicated carbons in the 1H nmr spectrum (6 points). Give the approximate chemical
shift for the protons on the starred (*) carbon (2 points).
O
O
*
2
4. Consider the ionic species given below. Give the hybridization of each indicated atom
(7 points).
C
O
N
4a. How many pi bonds are in this ionic species (1 point)? ______
4b. How many p orbitals are present in the above species (1 point)? _____
4c. The lone pair of electrons on nitrogen is in what type of orbital (1point)? _____
4d. The lone pairs of electrons on oxygen are in what type of orbital (1 point)? _____
5. Draw the structure of the following compounds (3 points each).
2-ethoxypent-2-ene
trans-1-chloro-3-methylthiocychexane
3
6. Name the following compound (2 points).
O
O
O
O
O
O
7. Give the reagent necessary to carry out the followings (8 points)
O-Na+
OH
O
O
O
S
O
O
O
O
O
O
H
H
H3C
H
CH3
Cl
4
8. Define the following terms or finish the following statements (3 points each).
a) sigma bond
b) pi bond
c) The sole requirement for resonance is the
9. In the bromination of 2-methylhex-2,4-diene (A) with NBS in the presence of light,
radicals B and C are two possible intermediates. (1) Circle the allylic carbons in A (2
points). (2) Using single headed arrors to indicate electron flow, draw the resonance
structures of B (4 points). (3) Draw the structure of second radical intermediate C (3
points). (4) Draw the brominated products resulting from intermediate B and circle the
major product (3 points)
+
A
C
B
B
5
10. Draw the products resulting from the following reactions (12 points)
Ph
+
O
CN
+
O
O
CO2CH3
+
CN
11. Draw the reasonable resonance structures for the following cations and anions (10
points)
O
O
N
6
12. Draw the structure resulting from the following reactions. Star (*) any stereocenters
and label them as to whether they are “R” or “S” (10 points).
OH
H Ph
O
Cl
+
N
H
Cl
NaOH
O
CF3
H 3C
MgBr
H
+
O
H
(1) ether
(2) H3O+
7