Even More Alkene Addition Mechanisms

1. Provide a complete curved-arrow mechanism for step 1 only in the following transformation:

X
r OCH"
\ 1. Hg(oAc)2, cH3oH

',{
rt X
.^ 2. NaBHo

AaO- tlat J
--l)
9o&. lu^*',
\
.V ,-, ttic+rr /*""^,
i\ ,/ 'i --'s
't ^du3 . L.o9*"
' 4oacfls
/"Tt H
/ LuoJ'Qt' FQ^.
fI-
Ac-O -,
(^o** *9e. a.L.rcn.o of *ycd ir. $A'l rt^uAor,,isn^l)

2.Predict the product of the following two-step transformation, and show a complete curved-arrow
mechanism for the step 1 only.
D
1. BD3, THF (D = deuterium)
/^la
(/ brr

fnrn,Pcslt
DrED. /(oxlr*+"^)
,N. )

6r-,eh*.= aY-
\,/ I t)
D

ts-^>

5" (+fi, L.*^" t?cds,,rltA

Z .+.rrrt e1*v*Oqg *f
aJk-r"u-)
 More Alkene Addition Mechanisms
1. Provide complete curved-arrow mechanisms for the following transformations.

Br2,CH30H
fl
H3C-O
/Br
\

,ba
,'-:B/\I
.tf
s Brz

\
\
('u'
______€
t)r*
 Alkene Addition: Reagents
1. Each of the following transformations can be carried out in one or two steps. Fill in the reagents required
for each step.

1. Bt?-

2.
x

1. Ht , ?alL

2.
)<

'"7\

X
rOH
1, tsHs,THF

H1O-, F^OH
2.

1 $cu, C,rtSol-l
T / ocH3

2.
-x-
 More Alkene Addition: Reagents
1. Each of the following transformations can be carried out in one or two steps. Fill in the reagents required
for each step.

1. Hzo, H+.ct.

2. >< *

1. Cl"

2x

1 BHj,TltF
. '/o'
Haor. , t.JaOH
2.

OH

F[(o*c). , H.o

a
1. )-

2. [aK]q

j. 6r", HzO

2.
 Alkene Addition : Products
1. Fill in each box with the organic product(s) of the indicated transformation.

cHcl3

(r-r -)

Br2, H2O

Wu. (+l-)

F" +'<'
1. oa

2. (CH3)2S

1. oa H"FA
2. H2O2,H2O
 Alkene Addition: Synthesis
1. Provide a complete synthesis of the desired products. You may use any inorganic reagents, plus any
hydrocarbons you wish.

l. os
Z. He"S
oc &t,HzO

l. Slb,THF
z. llro., Nla5l

7^
l. F[(a{,H.o
Z. tJqBHV -
/or \
A
OH
tsa
,,\
r
Y"
(H.o, H*..+.)
 Stereochemistry of Alkene Additions
'1. Fill in each box with the organic product(s) of the indicated transformation. Be sure to indicate the correct
stereochemistry. (lf the product is formed as a racemic mixture, please indicate thisl)

E^ Gr
Brz

ry ,{-z
B-
.IL \vl..
Ec-
(c".r^.;. d**,".q)

OH
t*.-l
v
Br2,H2O

E7 E
_r
OH

Cr..r*" {*:t+.c)

1. BH3,THF
2. H2O2, NaOH /FA- \A 'i
oH

(^".;. u^r+n)

-
H

Pd/c
M
 Making and Using Epoxides
1. Provide two different synthetic routes for the following transformation.

mCPtsA
€
o
l\.
r-r.c"/-\"u
(ptus enantiomer)

CHs

o
\ Ec- H6r (r3 +
IJcOH
,.""f\", (plusenantiomer)
I p-c,-Hrc'; H CH3

(+r-)
2. Predict the product.

o
Hgo* Ho 9ns
H.c.'f\',cH. >
H CH3

(enantiomerically pure)

o
NaOCH3 OH
H.c../\,,cH. ,..
H CH3 --+
cH3oH C+13

(enantiomerically pure) Ico ut

3. Each of the following transformations can be carried out in one or two steps. Fill in the reagents required
for each step. lf a second step is not needed, please put an "X" through the second box. (An epoxide may or
may not be involved in these transformations!)

1. TnCPBA

l't30@
2. (plus enantiomer)

1. osoq, 6ro

2.
x
 Putting lt Together: Synthesis
1. Propose multistep syntheses for each of the following transformations. Consider stereochemistry where
relevant. (Not every possibility is shown.)

OH C.6l^c.
I
HzSor rytCPtsA
o?
ca{-,
----t

(plus enantiomer)

(using only hydrocarbons as starting materials)

rz\ Sln+R {rc,.*Rc afiof;.*< attcaar
'r$ou c4^ $lbt^l L$,',?, te^f funr:-

$
:
r. "r;1'\,
O <qt I l;a'rn!6\ sgn{Ra1i5
:
ffi'.'w
(0" t5dal.oa4r?-;
..A *i_t &u"ie !9ctr*i"^ .^,llt bq
4ou.S2,l^.A.)
(o- o*r..r-.-o,*io^) t

:. *br^--l: . #
,lP*' I F"r..-

f . HF' --.-,-.-,-oH Fts., -rz Bc

l l z. rro.7 [
NqoH

xcorr\ rrtc a*.r'c arb*C.n. intffir

sbh,'l8$ii) or rt will
cir..\6.-;..^, {t"r{t19
^