Last Name First Name lD Number

Fill in the mis*ing preelnsr§ (trù mechadun)

ffi
Meo-
Y-
t-
* f-' ll *uJ*"u
\rr
Ms
tl
COoMe
,rt{e
__--->
,l

€ _ lll rl
\-*n" éor* ,Jb

ft.
\,1 Me-
li-
)l
*
A**
o

ìt

-
tto

.3. a) Treatn:ent crf oxime -d*'itir base audl{-chLorosucci*imide fcllowed by u

leads ro the f,or*ration of y-arnino alcohol B" Fror.ide the fu1t mechani.snr-tbr this

lron rl,-ould 3'ou nake the oxigre from osia-6-eflatr?

1) Nfte NCS x ?H.

--s
2) LiAJH4
r§Ao',
t1
+ HJNOH
SNr-{a
§
3' -4nother la.&]* to slttthesize 1.3 amiuo-*lcahol is to prepare titr,orre with a cope elirninatian anil
subsequent oxidarir:l. a] Fill the rnissing part {r,e*-eents prnduers}. b} Give an alten:atilre \À:av ro

s3.nthesize B.

.-\ r' -j&)lH-oH

\-)
.N l8s a H§o
- f -*§p
t,

Et 2) h€!* oFl _0
A.
hydroxylamine ,,NJ ?}HÀ
'NI
H1 -co0R
H0"

+ A,e- g
V4
0/
CI

-ùw -+>
C

-CH
àtrt
r *-,D

Cne+r
H Cllr
,ài ftQHr,
---P
-b r-+-§H
\".^NÉr
*' Cyulopentadiene B and its rler{1.'atir-es are usefi:l btri}riing bl*cks f*r Diels-§der reacri*nx.
o
.-4,
trsrRo
ll :0
\'
§tELg-&rbEq cl\/ct o
4ù\
\J
i\

\_/
'', . cr-tr).-cr $

crflcr
A - c endrE

a) At room tesìpexì*ttn"e Cyelope*tadiene B exi*ts ax its dirner A. Lrut c*n tre dissocicteil iuto tlre
mononreric form on lre*ting. hotide a rnechenisn: for this trcnsfouuati*n. l,Vhst kind of reastiCIu is
fhat? b) C3'cnopent*di*ne B ca* he chlorinated tÈ gire herachlorocyclapeutadiene C. ?lre reasfion
of the *hloroderi*ative C with umleic anirydrtde D o*ly prorid*s the endryrcduct E.
{nat tlle ero}.
Use orbital diagr*rnsli*teractions t* explain this cbseraati*n.

§. T1le reaction of anftruanj.lic acid A u ith a nitrite B {e.*s. aurS{ nitrite) le*ds to the lbrmation of *
Itighly reaetive inten:rediate C. Prer{de tlre Èrlt nreciranisu tbr rhis rrausfom*tion. Erhat {s the
n"lflre of tlre reactive inten:rediate C? ilurl (i]: tlie reactive i*ter:*edirte C can be tratrlped by
antlxacene D to gi.re praduct E)

r .r-i\,'\a't{+0

A B
o
HT rbH
+Ì=O'
wu
l.\ì{.f{,=9H

S. Proride the missi.ng corctitionr fi*r the tr"ausfennation aad §É1:e É1 possible Étere*ctreulical
crnfigurariotr of the pr*d*ct.

M&OOC MÈ

q::.*Q 1)
tt
llJ
N-BHq
0
*

,rffi Yte"

>f
%=

t,
10. The following reactions involve organometallic compounds. Fill in the missing reagents,
products and or reaction names.

Ò
HXS€S§
0t't

#*." l$eMgSr
-_-____*
Ei#" l(uHqì\+ (D()Pr|tr1

l;**;r
l-l
*-*t,*;* ffi §tilìo 0rss§-CoilFtlfig
nr*oV

I*Br
I
L
r{gtvr:r*Ht c-ooPqNG
^*
Pd{eAe}* '-F-l
H

t *q,*coo:
#YE' --,/Bt Hecr È=qcnoq
L,L, Pd(sA*k, t=Ar..rcoH
ElrFi

11. For cyclic alkenes, C-C bond rotation is not possible. Give the full mechanism and.product of
the following Heck reaction.

I
Fd{OAe}3
ilt+ §a§A*,0MF
*
rh
7. Gire tlre products far th* foll*r,i ilig rÉ{rÈtisns

\,,\u.V
irtsS @.Ef
t1

À lrÈP*,bsr>ffi
Jr. à?;?

t) *BllLi.l-leq I) n-Hul-i1t tea) \\

-78 0C 0 "C - room t6mporatur6 n
2t cnso§ -g**L eI GfhCID §-/-
f*tf

8' Fror''ide a one-step sysrlre*is for each of the tu's §o§Ipsffiidx belon. LIse starfi*g materials
ro*taining aot m:ore tfu.a* foru.carh*n fitom§.

r0 §F{

",r-".-*-J-*-il & ,

4
01
,-S/\ H + BOrfu.L'
s. Drau. t&e *redrarÉsm of the fotrl.o,nur.{ reactinn:
-$\r {- ,^-,nL;
{} ffi
r{ ri
II
2 *q,fut*p*ul{
rtl ,\
tl
-r-&*rt
A
H
1 l.*

(to p
Ux
nle,,l' *D +fl*;eoLr o [#uz
-L
-D
H:j 'à ,{3J, 015
 12. Provide reagent Yfor the Pd-catalyzed reaction to form product Z What is the name of this
reaction? How would you prepare reagent Xfrom alcohol \AP

S$t{e

*\#
*,[8s

til
\r/ ,,,gf*
F${fi} *nt-

G{.}{}} §se"
*asa
SoltoffiSHIR§

x Y 7

#
IIJ
\_#
o&#s
fl
0H

tr
o{[{§

\:,1

tf
0He
w x

13. Substituted cycloheptanone A is converted to bicyclic compound Dvia the following reaction
sequence:

1) LEA g-3Efd cfft" Fet{FPn}4

* --.."""..-..--".
cl ph!id{§o!fir-3}s KECOI

- Provide the structure of intermediate Cand the final product (D). What is the name of the last
reaction?
-

s
- Provide a synthesis of A starting from cycloheptanone.

\"-O't{
c, l-*{;e{} §. SU2U K \

b*fl o

0
rbà
0o aa
*l'-owu
Ò
c
-ò
e -r\oì-t
CIL
e-
\-rt
\taoNe-
---E
W._/-é
L]\
-.Jt-/L Olte

0
rla)\oH,