Test 3 Extra Synthesis Practice - Page Not Found
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1
Organic Chemistry I
Test 3
Extra Synthesis Practice Problems
Page 1: Synthesis Design Practice.
T
Page 2+3: Predict the Product Practice (including some that involve stereochemistry).
Page 4: Cis/trans Stereospecific reactions: which recipe to use; which E or Z alkene to use.
Page 5: Recognizing cationic/anionic/radical reactions, and reasonable intermediates/first steps
Page 6: Elements of unsaturation/hydrogenation problems; ozonolysis puzzle problems.
A. Provide reagents for the following transformations.
OH
Br
1.
Br
OH
2.
T
3.
Br
O
Cl OH
4.
Br
Br
5.
T 6.
HO
OH OH
O O
HO
7.
HO
2
B. Draw the major product for each of the following reactions or reaction sequences. You needn't bother
to show side products or minor products. For chiral molecules that are racemic , you needn't draw both
enantiomers. BE CAREFUL TO SHOW THE CORRECT ORIENTATION, AND THE CORRECT
STEREOCHEMISTRY IN CASES WHERE STEREOCHEM IS FACTOR. (3 points each).
T
H2SO4, heat
8.
9.
10. 11. 12. T 13. 14. 15.
16. T
17. 18. 19.
OH
Br
NaOH
Br
NEt3
HBr
HBr, peroxides
1. HBr, peroxides 2. NaOCH3 H2O, H+
1. Hg(OAc)2, H2O 2. NaBH4 1. Hg(OAc)2, H2O 2. NaBH4 3. H2SO4 1. BH3-THF 2. NaOH, H2O2 1. BH3-THF 2. NaOH, H2O2 1. Hg(OAc)2, CH3OH 2. NaBH4
Note: explicit stereochemistry must be drawn. The enantiomer would have been equally acceptable.
20. T
21.
22.
1. HBr 2. NaOCH3 Br2
Br2, H2O
Br2
23.
Br2, H2O
24.
Cl2
25.
Cl2
26.
T
27.
PhCO3H
28. Ph
PhCO3H
29. Ph
CH3CO3H, H2O
30. 31. Ph
CH3CO3H, H2O OsO4, H2O2
T
32.
33.
34.
OsO4, H2O2
1. O3 2. Me2S 1. O3 2. Me2S
3
Note: explicit stereochemistry must be drawn. The enantiomer would have been equally acceptable. This principle will apply for any of the reactions producing two chiral centers. Problems 23-32
4
C. Draw the alkene that would product the products shown. Make sure to make your drawing clear
whether the starting alkene was E or Z.
T 35.
Cl
Cl2
Ph
Cl
Br2, H2O
OH
36.
Br
OH CH3CO3H, H2O
37.
OH
OH OsO4, H2O2
38.
OH
T 39. 40.
1. BH3-THF 2. NaOH, H2O2
H3C H
Ph OH
PhCO3H
O
H 3C
CH2CH3
1. O3 2. Me2S
41.
D. What reagent(s) would you use to conduct the following transformations?
T
Ph
42.
OH
Ph OH
CH3
Ph
43.
H3C OH
Ph OH
5
E. Recognizing whether reaction mechanisms should be cationic, anionic, or radical; whether
intermediates should be cationic, anionic, or radical; and recognizing what could be reasonably
involved in the initial reaction step.
T 44. The transformation shown is common in many
biological systems. Which of the following HO statements is definitely, absolutely false? a. The first step in the mechanism probably
involves protonation of the carbonyl oxygen. b. The overall reaction involves an addition
reaction c. The mechanism is probably radical in nature
O H+
OH
H2O O
45. For the transformation shown, which of the
following statements is definitely, absolutely
false? a. The first step in the mechanism probably
involves protonation of a carbonyl oxygen. b. The overall reaction involves a substitution
reaction c. The mechanism is probably anionic in nature d. The first step in the mechanism involves
ethoxide anion grabbing a hydrogen.
OO
1. NaOEt
OEt 2. BrCH3
OO
OEt CH3
T
46. Shown is a reaction, and some possible
intermediates along the mechanistic pathway.
Given the reaction conditions shown, which of
OH
H+
NMe2 H2O
O + HNMe2
H
the following statements is true?
a. Structures A and B might be plausible
intermediates; structure C definitely isn't
O
OH
OH
b. Structures A and C might be plausible intermediates; structure B definitely isn't
c. Structures B and C might be plausible
A NMe2
NMe2 BH
C
intermediates; structure A definitely isn't
d. Structure A might be a plausible
intermediates; structures B and C definitely
aren't
47. Shown is a reaction, and some possible intermediates along the mechanistic pathway. Given the reaction conditions shown, which of
O
NaOMe
OO
Ph
Ph OCH3 MeOH
OCH3
Ph
T
the following statements is true? a. Structures A and B might be plausible
intermediates; structure C definitely isn't b. Structures A and C might be plausible
O
OH H3CO O O
Ph
A OCH3 Ph
B OCH3 Ph C
OCH3 Ph
intermediates; structure B definitely isn't
c. Structures B and C might be plausible
intermediates; structure A definitely isn't
d. Structure A might be a plausible
intermediates; structures B and C definitely
aren't
6
F. Elements of Unsaturation/Hydrogenation Problems. For each problem there will be multiple
satisfactory solutions.
T
48. Provide a possible structure for a Answer must show one alkene and one ring.
compound
with
formula
C5H8,
given
(Other structures also meet that requirement). H2/Pt test proved 1 alkene.
that it reacts with excess H2/Pt to EU=2 originally.
give C5H10.
So the other EU must be ring.
49. Provide a possible structure for a Answer must show two alkene and one ring.
compound with formula C6H8, given (Other structures also meet that requirement).
that
it
reacts
with
excess
H2/Pt
to
H2/Pt EU=3
test proved originally.
2
alkenes.
give C6H12.
So the other EU must be ring.
50. Provide a possible structure for a Answer must show two alkenes and two rings.
compound given that it
with reacts
formula C8H10, with excess H2/Pt
(Other structures also meet H2/Pt test proved 2 alkene. EU=4 originally.
that
requirement).
to give C8H14.
So the other two EU must be two rings.
51. Provide a possible structure for a Answer must show two alkene and one ring.
compound with formula C6H8, given that it reacts with excess H2/Pt to
(Other structures also meet that requirement). H2/Pt test proved 2 alkenes. EU=3 originally.
give C6H12.
So the other EU must be ring.
T
G. Ozonolysis: Draw starting chemicals that will undergo ozonolysis to produce the products
shown. In some cases there may be more than one satisfactory answer.
1. O3
H
O
52.
2. Me2S
O
53.
Any of
T three
answers
54.
1. O3 2. Me2S
OH
H O
1. O3 2. Me2S
H O
O
O
+
HH
HO
1. O3
H +
O
O
+O
55.
2. Me2S
OH
H
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