Chem 3351
Fall 2014 Midterm 3
Student ID
Name
page
points:
2
3
4
5
6
7
Total
(16)
(15)
(19)
(22)
(18)
(10)
(100)
Periodic Table
H
He
Li
Be
B
C
N
O
F
Ne
Na
Mg
Al
Si
P
S
Cl
Ar
K
Ca
Sc
Ti
V
Cr
Mn
Fe
Co
Ni
Cu
Zn
Ga
Ge
As
Se
Br
Kr
Rb
Sr
Y
Zr
Nb
Mo
Tc
Ru
Rh
Pd
Ag
Cd
In
Sn
Sb
Te
I
Xe
Cs
Ba
La
Ha
Ta
W
Re
Os
Ir
Pt
Au
Hg
Tl
Pb
Bi
Po
At
Rn
Fr
Ra
Ac
Chem 3351
Fall 2014 Midterm 3
Student ID #_____________
1. Draw the structure of the following compounds (6 pts).
A) 2-ethoxy-5-methylhexane
B) 2,3-pentanediol
C) 2-ethyl-3-methyloxirane
2. Indicate whether each of the following transformations is an oxidation, a reduction, or neither
(10 pts).
A)
B)
OH
O
C)
OH
NH 2
D)
E)
Br
O
OH
OH
Page 2 of 7
Chem 3351
Fall 2014 Midterm 3
Student ID #_____________
3. Arrange the following alcohols in order of increasing acidity in aqueous solution (3 pts).
(CH 3)3COH
CH 3CH2OH
CH 3OH
(CH 3)2CHOH
4. Draw a dashed line indicating the hydrogen bond between the following pair of molecules.
Identify the hydrogen bond donor and acceptor (6 points).
O
H 2O
5. Which of the following is the most stable carbocation (3 pts)?
6. Rank the following electrophiles in order of increasing reactivity in an SN2 reaction (6 pts)?
A)
CH 3CH2CH2Cl
CH 3CH2CH2I
(CH 3)2CHCl
CH 3CH2CH2Br
Page 3 of 7
Chem 3351
B)
Fall 2014 Midterm 3
CH 3CH2CH2OMs
CH 3CH2CH2OTf
Student ID #_____________
(CH 3)2CHOMs
CH 3CH2CH2OH
O
ROMs = R O S CH 3
O
O
ROTf = R O S CF 3
O
7. Provide the missing reagents and products for the following reactions (30 pts).
A)
PhCH 2CH2OH
THF
PhCH 2CH2ONa
O
CH 3CH2O S
O
CH 3CH2OH
CH 3
N
B)
(CH 3)3CBr
C)
CH 3CH2Br
CH 3CH2ONa
dilute H 2SO 4
CH 3CH2OH
CH 3OH
Mg
ether
D 2O
D)
CH 3(CH2)3CH2OH
PCC
CH2Cl2
Page 4 of 7
Chem 3351
Fall 2014 Midterm 3
Student ID #_____________
E)
H
Br
Ph
H 3C
CH 3CH2ONa
Ph
CH 3
CH 3CH2OH
F)
H
Zn-Cu
Ether
+
H
H
H
Cl
G)
H
H
+
Cl
(CH 3)3COK
(CH 3)3COH
H
H
H)
mCPBA
benzene
+
I)
H 3O
+
H 2O
8. Complete the syntheses shown below. Each synthesis may involve a sequence of several
reactions (16 pts).
O
A)
OH
Page 5 of 7
Chem 3351
Fall 2014 Midterm 3
Student ID #_____________
B)
HO
OCH2CH 3
7. Provide the mechanisms for the following reactions. Show every intermediate and all the
arrows required for each step of the reaction (20 pts).
A)
CH 3 OH
H 3C C
C CH 3
H
CH 3
H 3O
H 2O
CH 3 CH 3
H 3C C
C CH2
H
29%
H 3C
+
CH 3
C C
H 3C
CH 3
71%
Page 6 of 7
Chem 3351
Fall 2014 Midterm 3
B)
SH
I 2, NaOH
Student ID #_____________
S S
Page 7 of 7