CHEM 150
Assignment #7
(Due Thursday, Feb. 20th, in-class)
1) Give IUPAC names for each of the following compounds (hint: watch out for cis-/trans- in some cases). 1 point
each (part marks for small mistakes in name) 6 total
a)
b)
cis-2-methylcyclohexanol
4-bromophenol
para-bromophenol
c)
d)
3-methyl-2,3-hexanediol
3-methylhexane-2,3-diol
5-ethyl-1-octanol
5-ethyloctan-1-ol
e)
f)
cis-methylcyclopropanol
3-methyl4-heptanol
3-methylheptan-4-ol
2)
Classify each of the following alcohols as primary, secondary, or tertiary. (1 point each) 3 total
c)
b)
a)
3o
2o
1o
3) Draw the following alcohols: (1 point each) 4 total
a. 2-Methyl-2-heptanol
b. 3-phenyl-1-butanol
c. 3,5-Dimethylcylcohexanol
d. 3-Ethyl-2-pentanol
a)
b)
c)
d)
4) Write the structure of the expected, major product in each of the following reactions. 1 point each – 4 total
i)
H2SO4
H2O
ii)
catalyst
H2
iii)
H2O
H2SO4
In iii), because both double bon carbons in the reactant each have one H-atom attached, the OH group will have
about an equal likelihood of being found on carbon #3 in the alcohol as it would on carbon #2. Both would be
predicted to be “major” products in this case.
5) Draw the structure of the alkene product(s) that is (are) expected in each case. Indicate the major product,
where appropriate. (don’t deduct points if H2O not shown – 1 point for each organic structure + 1 for “major”
designation) 5 total
i)
H2SO4
H2O
180oC
ii)
H2SO4
H2O
180oC
iii)
H2O
H2SO4
180oC
H2O
major
6)
a.
b.
c.
Draw each of the following: (1 point each) 3 total
A skeletal isomer of 1-butanol
A functional group isomer of 1-butanol
A positional isomer of 1-butanol
a)
or
b)
any one of these
c)