Key to Homework 5
Chapter 15 (due Tuesday 11/15)
Chem 102, Fall 2005
1. Give the name for each of the following structures:
O
O
H
a)
Cl
b)
Cl
2,4-dimethylpentanal
3,4-dichlorocyclohenanone
O
c)
O
O
d)
H
H
OH
OH
ortho-hydroxybenzaldehyde
2-hydroxy-3-oxobutanal
2. Draw the structure for each of the following names:
a) propanone (what is the common name for this one?)
O
Acetone
b) 3-cyclopentyloctanal
O
H
3. Rank the following compounds in order of increasing boiling point (number them 14 from lowest to highest):
O
O
HO
H
2
1
4
3
4. Fill in the missing reactant(s) or product(s) for each of the following reactions (use
NR for no reaction):
O
OH
OH
H 3O+
a)
H
H
O
O
Tollens
b)
H
OH
O
NaBH 4
c)
OH
H
d)
O
NaBH4
e)
O
Tollens
OH
OH
or
OH
NR
O
Acid
O
f)
H
Cat.
OH
5. Butanone is much more soluble in water than diethyl ether. Explain why using
drawings to illustrate your answer.
Both compounds can H-bond with water. However, butanone is more soluble because
the carbonyl is more polar than the ether group, so there are stronger intermolecular
forces between butanone and water than between diethyl ether and water (stronger Hbonding with water).
Stronger attraction
O
O
H
H
O
Vs.
H
H
O