Name:
Organic Chemistry
Chem 231 B
Whittier College Department of Chemistry
Test #4, May 7, 2004
115 points
1. Multiple Choice: Choose the best answer to following problems: (16 pts = 4 pts each)
1. Which of the following reacts most slowly when treated with Br2 and ferric bromide (FeBr3)?
O
O
O
NH2
Br
a.
b.
c.
d.
e.
2. In an electrophilic aromatic substitution reaction, chlorine is:
a. A deactivator that directs to the meta position
b. A deactivator that directs to the ortho and para position
c. An activator that directs to the meta position
d. An activator that directs to the ortho and para position
e. A deactivator that does not direct to any specific position
f. does not activate nor deactivate and does not direct to any specific position
3. What series of reagents would you use to affect the following synthetic transformation?
OO
?
a. 1. CH3Br / THF 2. Work-up in acidic water
b. 1. NaCN / DMF 2. NaBH4 / NaOH / H2O 3. Azeotrope
c. 1. CH3MgBr / Et2O 2. Work-up in acidic water
d. 1. (CH3)2CuLi / THF 2. Work-up in acidic water
e. 1. LDA / THF 2. CH3Br in THF 3. Aqueous work-up
4. Under azeotropic acidic conditions, which of the following structures is the most abundant form of
acetaldehyde (CH3C(O)H)?
a
.
b.
c.
O
H
O
H
H
O
H
HO H
HO
O O
O
d.
e.
