Recitation CHEM 2325-04.11mihaela/RecitationC... · 4/11/2015 · Recitation 04/11/2015 CHEM 2325...
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Recitation 04/11/2015 CHEM 2325 1. Supply the product for each step in the following procedure. The answer for the second box has a molecular formula of C 5 H 8 N 2 O. b.When the final product in the last box is heated with basic silver oxide (Ag 2 O, ) two nitrogen containing compounds are obtained. Draw these compounds. c. Circle the answer in part b that is more basic. H O O OH SOCl 2 H 2 N NH 2 buffer LAH CH 3 I excess
Transcript of Recitation CHEM 2325-04.11mihaela/RecitationC... · 4/11/2015 · Recitation 04/11/2015 CHEM 2325...
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Recitation 04/11/2015 CHEM 2325 1. Supply the product for each step in the following procedure. The answer for the second box has a molecular formula of C5H8N2O.
b.When the final product in the last box is heated with basic silver oxide (Ag2O, ) two nitrogen containing compounds are obtained. Draw these compounds. c. Circle the answer in part b that is more basic.
H
O O
OH
SOCl2 H2NNH2
buffer
LAH
CH3I
excess
-
2. Supply the preferred product for the following reactions. Assume proper work-up for each step. a.
b.
c.
d.
e.
f.
OH
1) H2SO4, 2) KMnO4,
O O
OHBH3 • THF
O
OH1) SOCl2
2) LiAl[OtBu]3H
O
NHCH3
O
HOLAH
O
O
MgBr
O
HPPh3
-
g.
h.
i.
j.
3. Draw all the resonance structures of the conjugated bases formed by the removal of the labeled protons (Ha, Hb, and Hc) in 1,3-cyclohexanedione and acetanilide. For each compound, rank these protons in order of increasing acidity and explain the order.
O
OCH3CH3MgBr
O
H
1) HS SH TsOH2) BuLi3) CH3Br4) H+, HgCl2
N1) H2O22)
NH2O
HH+
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Keys 1. Supply the product for each step in the following procedure. The answer for the second box has a molecular formula of C5H8N2O.
b. When the final product in the last box is heated with basic silver oxide (Ag2O, ) two nitrogen containing compounds are obtained. Draw these compounds.
c. Circle the answer in part b that is more basic. 2. Supply the preferred product for the following reactions. Assume proper work-up for each step. a.
b.
c.
H
O O
OH
SOCl2 H2NNH2
buffer
LAH
CH3I
excess
H
O O
ClN
NH
O
HN
NH
N
N
N N
OH
1) H2SO4, 2) KMnO4,
O
O
OH
O O
OHBH3 • THF
O
OH
O
OH1) SOCl2
2) LiAl[OtBu]3H
O
H
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d.
e.
f.
g.
h.
i.
j.
O
NHCH3
O
HOLAH
NHCH3HO
O
O
MgBr OHOH
O
HPPh3
O
OCH3CH3MgBr
OH
O
H
1) HS SH TsOH2) BuLi3) CH3Br4) H+, HgCl2
O
N1) H2O22)
NH2O
HH+ N
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3. Draw all the resonance structures of the conjugated bases formed by the removal of the labeled protons (Ha, Hb, and Hc) in 1,3-cyclohexanedione and acetanilide. For each compound, rank these protons in order of increasing acidity and explain the order. 1,3-cyclohexanedione: increasing acidity Hb < Ha < Hc Acetanilide: increasing acidity Ha < Hc < Hb
