51A Practice Problems 4
Fall, 2014
1. For each set, write in the box a letter or letters which correctly completes the statement:
O
a.
NH3
CH3OH
NH4
CH3COH
CH4
A
B
C
D
E
a) Which compound is the least acidic?
b) Which compound is the most acidic?
c) Which compound has the strongest conjugate base?
Even harder: Rank these in order of decreasing acidity (Most acidic = 1)
O
b.
O
CH3CO
OCH2CH3
A
B
O
CF3CO
OCH2CF3
C
CI3CO
D
E
a) Which compound is the least basic?
b) Which compound is the most basic?
Even harder: Rank these in order of decreasing basicity (Most basic = 1)
2. Identify nucleophiles and electrophiles in each of the following reactions. Which compounds are
also Lewis acids and bases? Which compounds are also Brönsted acids and bases? Draw curvy
arrows to show formation of each product.
BF3
a. CH3CH2SCH3
b.
c.
C
C
+
+
+
BF3
CH3CH2SCH3
I
C
HI
C
I
H
+
I
3. Which of the following compounds has the highest boiling point? The lowest boiling point?
O
CH3CH2CH2CH2OH
O
HCCH2CH2CH3
CH3CH2COH
CH3CH2CH2CH2NH2
4. Circle each functional group and write the name of the functional group
Ph
CH2
O
OH
O
C
CH CH2 CH C
OH
NH2
O
5.
CH3CH2COH
A
CH3
CH3CH2N
CH3CH2CH2F
C
D
CH3
B
CH3OCH3
F
CH3CH2NHCH3
CH3CH2CH2Br
G
CH3OCH2CH2OH
H
a) Which compound(s) will form hydrogen bonds between its molecules?
b) Which compound(s) will form hydrogen bonds with a solvent such as ethanol,
but cannot form hydrogen bonds between its molecules?
c) Name any functional groups.
6. Indicate with an arrow the electrophilic site in each of the following molecules:
H
O
B
H3C Cl
H3C
CH3
H
H
7. Indicate with an arrow the nucleophilic site in each of the following molecules:
H3C
NH2
H3C
O
CH3
H2C
CH2