Chemistry Reference
In-Depth Information
11.
Given a small group of compounds, including alcohols, phenols, and hydrocarbons,
arrange them in order of water solubility, and construct a scheme for separating them
based on acidity differences.
12.
Given a group of compounds with similar molecular weights but differing potential for
hydrogen bonding, arrange them in order of boiling point.
13.
Draw the resonance contributors to phenoxide or substituted phenoxide ions, and
discuss the acidity of the corresponding phenols.
14.
Account for the acidity difference between alcohols and phenols.
15.
Write equations for the reaction of a specific alcohol or phenol with sodium or sodium
hydride or with an aqueous base (NaOH, KOH).
16.
Write the structures for all possible dehydration products of a given alcohol, and
predict which product should predominate.
17.
Write the steps in the mechanism for the dehydration of a given alcohol. Given
alcohols of different classes, tell which dehydration mechanism is most likely, and what
the relative dehydration rates will be.
18.
Write equations for the reaction of a given alcohol with HCl, HBr, or HI, with cold,
concentrated H
2
SO
4
or HNO
3
, with PCl
3
or PBr
3
, with thionyl chloride (SOCl
2
), or with
an oxidant such as chromic anhydride or PCC.
19.
Write the steps in the mechanism for conversion of an alcohol to an alkyl halide upon
reaction with a hydrogen halide.
20.
Write equations for the reaction of phenol with dilute aqueous nitric acid and with
bromine water.
21.
Contrast the acidity of alcohols and thiols. Also contrast their reactivity toward oxidizing
agents.
Write equations for the reaction of a given thiol with Hg
2+
, base, or an oxidizing agent
such as H
2
O
2
.
22.
ANSWERS TO PROBLEMS
Problems Within the Chapter
7.1
a.
Number from the hydroxyl-bearing carbon:
b.
cyclopentanol
c.
The alcohol takes precedence over the double bond.
4321
H
2
CCCH
2
CH
2
OH
3-buten-1-ol
7.2
a.
b.
c.
123
4
5
CH
3
CHC
CCH
3
OH
OH
3
H
3
C
1
2
