Download Don`t forget to study the generic functional groups and the common

ALCOHOLS & PHENOLS PROBLEMS
Don’t forget to study the generic functional groups and the common alkyl groups (isobutyl, etc).
1. Name the following compounds using IUPAC and, where possible, common names.
a)
d)
OH
H3C
HO
e)
b)
HO
CH(CH3)2
H2C
OH
CH3CCH2CH2
OH
f)
OH
CH3
CH
CH
CH
CH3
c)
HO
CH3
g)
OH
2. Draw structures of the following compounds:
a) glycerol
d) hydroquinone
b) m-cresol
e) -naphthol
c) resorcinol
f) allyl alcohol
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ALCOHOLS & PHENOLS PROBLEMS
3. Give IUPAC names and, where possible, common names for the following compounds.
a)
OH
d)
CH3
CH2
CH CH2 CH CH3
CH3
HO
CH3
e)
b)
H3C
C
OH
CH3
OH OH
Br
CH2CHCH2CH2CHCH3
f)
c)
OH
OH
OH
4. Draw structures of the following compounds
a) isoamyl alcohol
d) 2-ethyl-2-buten-1-ol
e) trans-2-ethyl-3-methyl-2-penten-1-ol
b) 1-cyclopentyl-1-phenyl-2-propanol
c) cis-2-iodocyclohexanol
f) (E)-1-chloro-1,2-cyclobutanediol
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ALCOHOLS & PHENOLS PROBLEMS
5. Draw the structures of the products of 1-methylcyclohexanol with the following reagents
a)
OH
HBr, H2O
CH3
b)
Na
c)
d)
H2SO4
cold
Na2CrO4, H2SO4, H2O
e)
PBr3
6. What Grignard and what carbonyl will react to produce the following. Draw structures of all
possible combinations.
OH
C(CH3)2
7. What hydride and what carbonyl will react to produce the following. Draw structures of all
possible combinations.
CH3
CH3
OH
C
CH2
CH3
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ALCOHOLS & PHENOLS PROBLEMS
8. List the reagents needed for the following transformations
a)
CH3
CH2
b)
CH3
CH
c)
CH3
CH2
CHBr
CH
CH3
CH3
CH3
CH(OH)
CH3
CH3
CH2
CH3
CH
CH
CH3
CH(OH)
CH2
CH3
CHBr
CH3
O
d)
e)
CH3
CH2
CH(OH)
CH3
CH3
CH2
CH(OH)
CH3
f)
COOH
g)
COOH
CH3
CH3
CH2
CH2
C
CH3
CHCl
CH3
COOH
CH2OH
9. Number the following compounds in order of acidity, i.e., 1 = most acidic, 4 = least acidic
OH
COOH
OH
NO2
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ALCOHOLS & PHENOLS PROBLEMS
10. Write equations to show how these reactions can be carried out. More than one step may
be necessary. There are marks assigned for each intermediate product (not charged
transition states) and there are marks for the reagents used; so list them all. No marks are
assigned for mechanisms
OH
a)
CH2
CH2
OH
CH
CH3
b)
CH2
c)
CH2
CH2OH
OH
OH
CH
OH
CH3
C
CH3
CH3
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ALCOHOLS & PHENOLS PROBLEMS
11. Write equations to show how the following transformation can be carried out. More than one
step may be necessary. There are marks assigned for each intermediate product (not
charged transition states) and there are marks for the reagents used; so list them all. No
marks are assigned for mechanisms
OH
CH2CH3
OH
12. For the following reaction:
a) Write products for the reaction
b) Show the mechanism of the reaction
c) Calculate pKeq
O
H
Na+OH-
13. Using arrows, push electrons to show the full mechanism of the reaction shown below.
Draw in all lone pairs of electrons on reagents, intermediates and products. Also name
CH3
CH3
the type of reaction
H3C
C
O
H
H
Cl
H3C
C
Cl
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ALCOHOLS & PHENOLS PROBLEMS
14. Write products of the following reactions. Show the major product(s) but mechanisms or
charged intermediates are not required
CH3
a)
b)
KOH
Br
H3C
PCC in CH2Cl2
CH
CH2
OH
H3C
OH
c)
Jones Reagent
CH
CH3
O
d)
1. Cl
CH3
C
H3C
CH2
S
CH3
O
OH
H
LiAlH4
then
2.
+
H3O
e)
Na
OH
f)
PBr 3
OH
POCl3
g)
CH3CH2CH2CH2OH
N:
h)
H3C
SOCl2
CH
CH2
OH
H3C
O
i)
CH2
CH
C
1. LiAlH4
O
CH3
+
2. H3O
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ALCOHOLS & PHENOLS PROBLEMS
15. Draw the structures of a Grignard and a carbonyl compound that can be used to synthesize
the following alcohols. Show all possible combinations.
Also draw the structures of any carbonyl compounds that can be reduced by a LiAlH4 to
prepare these compounds
a)
OH
CH2CH3
C
CH2CH3
b)
OH
C
H
H
16. Write equations to show how the following transformations can be carried out. More than
one step may be required. Show all reagents and the products of each step, but do not
show any transition states. Mechanisms are not required
a)
OH
OH
CH3
b)
c)
OH
O
CH3
CH3
O
CH2CH3
CH2CH2CH3
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ALCOHOLS & PHENOLS PROBLEMS
17. Write a mechanism for the following reaction. To write a mechanism, you must show the
movement of electrons using arrows.
It will be best to redraw the structure showing any lone pairs of electrons and any bonds
involved in the reaction.
OH
H2SO4
C(CH3) 3
CH
CH3
(CH3) 2C
C(CH3) 2
18. Draw the structure(s) of all reagents which would give the following alcohol when reduced
with LiAlH4
(CH3)2CHCH2OH
19. Draw the structures of all sets of reagents that would give the following alcohol when
reduced with a Grignard reagent. Show Grignards as well as other reagents.
OH
CH3CH2CCH2CH3
CH3
20. Draw the formulas or structures of the products of the following reactions ...
a)
H3C
POCl3
OH
N
b)
H3C
PBr3
OH
H3C
cold KMnO4
aqueous
OH
c)
H3C
d)
hot concentrated
HNO3
OH
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ALCOHOLS & PHENOLS PROBLEMS
21. Draw and name the products of this reaction
H3C
K
OH
22. Write equations, including reagents needed to produce the following products. More than
one step may be required. Show all steps and the products formed along the way. Do not
draw mechanisms or show charged transition states
a)
CH2CH2OH
b)
CH2OH
Br
OH
CH2
CH3
OH
c)
CH2Br
CH
d)
H3C
H3C
O
H3C
C
C
OCH3
C
H3C
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