Practice 8-1
Give the IUPAC name of each of the following alcohols:
OH
OH
b)
a)
CH3
CH2CH3
c)
d)
CH3 - CH2 - CH - CH2 - CH2OH
OH
Answer
a) 4-methyl-4-heptanol
b) cyclohexanol
c) 3-ethyl-4-methyl-2-hexanol
d) 3-ethyl-1-pentanol
8-1
Practice 8-2
Classify the following alcohols as primary, secondary, or tertiary:
CH3
a) CH3 - CH2 - CH - CH2 - CH2OH
b)
CH3
c) CH3 - CH2 - C- CH2 - CH3
OH
d)
OH
OH
Answer
Locate the carbon bonded to the-OH group and then count the carbons
directly attached to that carbon.
a) primary alcohol
b) secondary alcohol
c) tertiary alcohol
d) secondary alcohol
8-2
Practice 8-3
Give the products for each of the following dehydration reactions. Name each
reactant and product.
OH
H2SO4
a) CH3-CH2-CH-CH2-CH3
OH
b)
heat
H2SO4
heat
Answer
OH
H2SO4
a) CH3-CH2-CH-CH2-CH3
heat
CH3-CH2-CH=CH-CH 3 + H2O
3-pentanol
OH
b)
H2SO4
heat
cyclohexanol
2-pentene
+ H 2O
cyclohexene
8-3
Practice 8-4
Write a chemical equation showing reactant and product for each of the
following. If no reaction occurs, write “NR”.
a) oxidation of 2-methyl-1-propanol
b) oxidation of 3-methyl-3-pentanol
c) oxidation of cyclobutanol
Answer
CH3
CH3
[O]
a) CH3-CH-CH2OH
CH3-CH-C
O
H
CH3
[O]
b) CH3-CH2-C -CH2-CH3
NR
OH
OH
[O]
O
c)
8-4
Practice 8-5
Draw structures for each of the following
a) 4-chloro-3,5-dimethylphenol
b) 2,3,5-triethylphenol
c) pentachlorophenol
d) ethyl cyclobutyl ether
e) cyclopropyl propyl ether
f) dicyclohexyl ether
Answer
OH
OH
a)
CH2CH3
b)
CH3
Cl
CH2CH3
CH3CH2
CH3
OH
c)
e)
Cl
Cl
Cl
Cl
Cl
O-CH 2-CH2-CH3
d)
f)
CH3-CH2-O -
O
8-5
Practice 8-6
Draw structures corresponding to the following names:
a) 2,2-dimethylcyclopentanone
b) 2,4,6-trimethylheptanal
c) bromopropanone
d) dichloromethyl ethyl ketone
e) dichloroacetaldehyde
f) 2,4-dimethylbenzaldehyde
Answer
O
a)
O
b)
O
O
c)
d)
Br
Cl
Cl
O
C-H
O
e)
Cl
CH3
f)
Cl
CH3
8-6
Practice 8-7
Write a chemical equation showing reactant and product for each of the
following. If no reaction occurs, write “NR”.
a) oxidation of 5-methylhexanal
b) oxidation of 3,3-dimethylpentanal
c) oxidation of 3-ethylcyclohexanone
Answer
CH3
O
a) CH3-CH-CH2-CH2-CH2-C
H
CH3
b)
O
[O]
CH3-CH2-C-CH2--C
CH3
[O]
CH3
O
CH3-CH-CH2-CH2-CH2-C
OH
CH3
O
CH3-CH2-C-CH2--C
H
CH3
O
c)
[O]
OH
NR
8-7