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Transcript 
(1) Predict the major product from each reaction. If you expect no reaction, indicate.
note: aqueous work-up is implied for all reactions.
(a)
EtO2C
CO2Et
(c)
NH2
OAc
OAc
O
AcO
AcO
OH
2) HCl, H2O, heat
NHAc
(b)
O
1) LDA, PhCH2Br
AgNO3
O
AcO
AcO
OH
O
Br
OR
OR
OR
OH
OH
OH
KOH
O
haet
3X
CH3(CH2)14CO2K
R=CH3(CH2)14C
NH2
OH
(d)
O
NH2
1) Br2, PBr3
O
2) NH3 (excess)
O
O
(e)
Ph
OH
NHBOC
N
(f)
O
O
OMe
CO2Et
NH2
DCC
Ph
O
N
H
NHBOC
N
H
OMe
N
H
CO2Et
O
OMe NH2
1) NH3, HCN
OMe
(g)
CO2H
CHO
2) HCl, H2O
NH2
O
O
(h)
O
NH3, NaCNBH3
O
O
(2) Give a detailed mechanism for the following reaction, show all steps.
OAc
OAc
AcO
OAc
AcO
OAc
O
OAc
H
1) HCN
AcO
OAc
O
Ph
2) LDA, PhCH2Br
3) MeOH, HCl
OMe
OAc
O
OAc
CN
AcO
OAc
O
Ph
OAc
AcO
OAc
OAc
O
H
AcO
NC
OAc
OAc
O
Li
AcO
NiPr2
Ph
NC
NC
HOMe
OAc
O
H+
PhCH2-Br
(3) Complete the following roadmap problem.
O
O
O
1) mCPBA
3) TMSCl, Et3N
2) NaN3
4) H2, Pd/C
HO
N
OCH3
4) FMOC-Cl, pyridine
6) Piperidine
5) NH2OCH3
7) CH2O, NaCNBH3
HOAc
TMSO
OCH3
8)Ac2O, pyridine
TMSO
10) OAc
AcO
OAc
O
HO
Br
AgNO3
HO
N
NHFMOC
N
9) TBAF
TMSO
N3
NCH3Ac
OH
OCH3
NHCH3
OH
O
O
11) NaOH
H3CHN
N
OCH3
NH2
(4) Propose a mechanism for the following enzymatic transformation
neryl pyrophospahte
enzyme
-H+
OPP
H
(metnyl cation)
(5) For the following aminosugar, draw the enantiomer
H2N
HO
H
H
CHO
H
H
OH
OH
CH2OH
H
H
HO
HO
CHO
NH2
OH
H
H
CH2OH
(6) Draw this compound in the chair form.
HO
HO
OH NH
2
O
H
OH
(7) Give the product and a mechanism for the following reaction.
O
1) TFA
MeO
NH
O
O
MeO2C
2) NaCNBH3
HOAc
O
N
H
H+
H-
MeO2C
N
H
O
MeO
NH
O
H O
MeO2C
H2O
O
MeO
-CO2
NH
H O
N
H2
O
MeO
MeO
NH2
O
O
MeO2C
HO
H+
O
O
PT
N
H
H
O
O
NH2
(8) Using benzene and and any other organic reagents with less than six-carbons, design a synthesis of the
following unnatural amino acid.
O
OH
NHFMOC
OMe
Br
1) Br2, FeBr3
2) HNO3, H2SO4
Br
1) Sn, HCl
2) NaNO2, HCl
3) Cu2O, H2O
OH
NO2
1) NaOH, Me2SO4
2) Mg, CuI then
O
OMe
O
O
OMe
OMe
1) KOH
2) Br2, PBr3
then H2O
OH
Br
OMe
1) NH3 (excess)
2) FMOC-Cl
target
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