Page 1 C HAPTER 9 HW: A LCOHOLS + E THERS ALCOHOL + ETHER NOMENCLATURE 1. Give the IUPAC name for each compound. Include cis/trans or R/S stereochemistry if necessary. Structure Name Structure Name 2. Give the IUPAC or common name for each compound. Include cis/trans or R/S stereochemistry if needed. Structure Name Structure Name HO OH OH CH 3 OH Cl OH HO O O OCH 2 CH 2 CH 3 O O OH O O
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Page 1
CHAPTER 9 HW: ALCOHOLS + ETHERS
ALCOHOL + ETHER NOMENCLATURE
1. Give the IUPAC name for each compound. Include cis/trans or R/S stereochemistry if necessary.
Structure
Name
Structure
Name
2. Give the IUPAC or common name for each compound. Include cis/trans or R/S stereochemistry if
needed.
Structure
Name
Structure
Name
HO OH OH
CH3
OH
Cl
OH HO
O OOCH2CH2CH3
O
O OHO
O
Page 2
REVIEW OF ALCOHOL SYNTHESES
3. Provide the starting alkyl halide and reagents needed in order to produce each alcohol through a substitution reaction.
WILLIAMSON ETHER SYNTHESIS
4. What is the purpose of the sodium hydride (NaH) in the following reaction?
5. Give the curved arrow mechanism for the following reactions.
a. c.CH3OHOH
b. d.OHOH
CH3OH CH3OCH3a. NaHb. CH3I
CH3OH CH3OCH3a. NaHb. CH3I
a.
b.OH O
a. NaHb. I
c. Bra. NaHb. CH3OH +CH3OH
Page 3
6. Give the major organic product for the following reactions.
7. Using the Williamson Ether Synthesis, show a synthetic route (complete with reagents) that efficiently
produces each ether below.
8. Provide the reagents needed to complete each reaction.
a. OHa. NaHb. CH3Br
d.a. NaHb.
OHI
b.OH a. NaH
b. CH3CH2CH2Bre.
a. NaHb. BrOH
c.a. NaHb.CH3OH Cl f.
OH a. NaHb. Cl
a. OCH3
b. O
c.OCH2CH2CH3
Cl OCH2CH3a.
OH OCH2CH3b.
Page 4
INTRAMOLECULAR REACTIONS
9. Give the curved arrow mechanism for the following reaction.
10. Give the major organic product of each reaction.
DEHYDRATION REACTIONS
11. Give the curved arrow mechanism for each reaction. Include the Lewis structure of the acid in your mechanism.
Cl
OHNaH O
a. Cl NaHOHHO
Br NaHb.
a.con. H2SO4
heatOH
b.OH
con. H2SO4
heat
c.OH con. H3PO4
heat
Page 5
12. For the following reaction, a. Draw the curved arrow mechanism.
b. Use the mechanism to identify two reasons why “acid” is a catalyst in the dehydration reaction.
c. Draw the energy diagram.
13. Draw all probable dehydration products for these reactions, including stereoisomers. Then decide which should be the major product and briefly explain your answer.
a.con. H2SO4
heatOH
b.OH con. H3PO4
heat
c.con. H2SO4
OH
Δ
d.con. H3PO4
heatOH
OH con. H2SO4
heat
Page 6
HYDRIDE AND ALKYL SHIFTS
14. Draw the intermediate formed after each mechanistic step.
15. What is a possible driving force (or reason) for the rearrangement in:
a. Problem 14a?
b. Problem 14c?
16. Give the curved arrow mechanism for each reaction. Include the Lewis structure of the acid.
Reaction
a.
b.
CC
H
CC
H
H
H
H
H H
a.H CH
HH
b.
H3C CH3
c.H3C
d.
con. H2SO4
heatOH
con. H2SO4
Δ
OH
Page 7
c.
d.
17. Identify which of the reactions W-Z would synthesize 3,3-dimethylcyclopentene most efficiently (with
the fewest competing products). Then explain why the other routes are less efficient.
con. H3PO4
heatOH
OHcon. H2SO4
Δ
OHcon. H2SO4
heatW
BrKOC(CH3)3X
Br
KOC(CH3)3Y
OHcon. H2SO4
heatZ
3,3-dimethylcyclopentene
Page 8
ALCOHOL REACTION WITH HX
18. Give the curved arrow mechanism for each reaction.
Reaction
a.
b.
c.
PBr3, SOCl2, AND TOSYLATE REACTIONS
19. Fill in the boxes with the organic product from each reaction.
HBrOH Br
HICH3
ICH3
OH
OH
HClCl
OH HNaH CH3I
TsCl
py.KN3
OH H
SOCl2 KN3OH H
Page 9
COMBINED ALCOHOL REACTIONS
20. Give the major organic product for each reaction. Consider plausible rearrangements.
a. HCl
OHi.
Cl SO
OCH3 OH py.
b. HIOH
OHa. SOCl2
b. KOCH2CH3
j.
c. HBrHO OH a. TsCl, py.
b. NaN3
k.
d. PBr3OH OH a. PBr3
b. NaCNl.
e. SOCl2OH OH a. TsCl, py.
b. O
ONa
m.
f. CH3OHTsCl
py.
OHHBr
CH3
n.
g.OH
NaHD
OH
HClo.
h.HO
PBr3
Page 10
21. The synthesis of the product shown in reaction L (call it product Q) is best achieved by this method. Explain why methods M-O will not effectively synthesize product Q.
EPOXIDE REACTIONS
22. Give the curved arrow mechanism for the following reactions.
OH
CH3a. PBr3
b. NaSHSH
CH3
(L)
Q
OH
CH3
(M) NaSH
OH
CH3
(N) H2SO4H2S
OH
CH3
(O)a. TsCl, py.
b. NaSH
a.NaOHO
OH
OH
H2O
b.H+O
OCH2CH3
OH
CH3CH2OH
c. KOCH2CH3O
ClCH3CH2O
O
DMF
Page 11
23. Concerning the following two reactions:
a. Explain the regioselectivity of the reactions.
b. Explain the stereoselectivity of the reactions.
24. Give the major organic product for each reaction. Indicate if a racemic mixture is formed.
OCH3
NaSHH2O
OH
SH
CH3
HClOCH3
CH3
OH
Cl
a.CH3CH2OK
Oe.
O
CH3
H+
CH3OH
b.H+
(CH3)2CHOH
Of.
O
CH3
KOHH2O
c. HBrO
g.O
HI
d.NaCNH2O
O
h. O HC C
b. H2O
a.
Page 12
COMBINED ALCOHOL + EPOXIDE REACTIONS
25. Give the major organic product for these reactions. Consider plausible rearrangements and indicate if a racemic mixture is formed.
a.a. NaH
OH
CH2CH3b. CH3CH2I
e. HBrO
b.NaOHH2O
O
f. HI
OH
c.con. H2SO4
OH
CH3
heatg. NaI
OTs
H3C
d. PBr3
OH
CH3O
h.
CH3
O
H
KCNH2O
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