EtMe
EtMe
HH
HO H
O
HH
Br
Br
MeH
OH
O
Br
Br 1) 2 eq. NaNH2
2) H2O
1) Br2
2) 2eq. NaNH2
3) H2O
Li / NH3
H2/ Pd-C
H2/ Lindlar's
catalyst
1eq. HBr
1) NaNH2
2) CH3Cl
3) H2O
*
*
*
4 C or fewer
CH211 ALKYNES Problem Set
1. Provide the products for the following reactions. Provide the mechansims for the reactions that are starred.
a)
b)
c)
d)
e)
f)
g)
h)
i)
j)
k)
l)
m)
n)
o)
2. Provide synthesis for the following molecules from the given starting materials. Work backwards first! Do the retrosynthetic analysis,
do the forward steps.
a)
b)
c)
d)
e)
f)
relative, not absolute stereochem.
Br2
HgSO4, H2SO4
H2O
H2/ Lindlar
1) NaNH2
2) PhCH2Br
3) H2O
Li / NH3
1) BH3
2) H2O2, H2O,
KOH
3 C or fewer
3 C or fewer
HBr
Br2
*