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(xaun /,
- Providea skeletal
(line)structurefor thefollowingmolecules.
[6 pointsl
a) (22,
4E)-3-ethyl4methyl-2,4-hexadiene
b) (32, 5D -3-&o1no-3,5-octadiene
- Namethefollowingmoleculeusingthe IUPACor commonnomenclature system,L3pointsl
(Zf,qS)-
),-rLtchlo,o
-l<n - S-yn<
o-cc
- Whichof thefollowingcompoundswill bemorereactive
halohydrin?You mayassumethealkeneshavesimilare
212t\
ar.'.t * l[ Sa-
graL,\;?r- -\h<
nror<
ai,{{ic.ql_l.
to
{t."-
'}0o^
'fhe
u(zcVon
u-i Vf-
,tv-riwi,, L\
brorn.r,n
i",^..
\on,
*atc,n
'l
important structures
or intermediatesin youranswer.[
{hr
-C+t:
gfrr^.*,nra .fint
ar+''''+'
an <t^i"J'l wltl b'
h\athtv-
$ -{o.rn
btz -clt
iA-t{v
'''n.ll-,
-i '
( tt'c'a
":slanNzr
r'^t+io't)
J1n p,AlJ$on,
l[^u r'
*"#,./.n"-;"'
A
at!1ae r^avz
llnz
t^\w^z
\e
v
h,.cit":ghi
llc (has
l<ss otrrt
,{n,^t,!)
So
t{-',s l.ss
Li@Lti fc atlaas
'th<
Pr Jra^
{-1'€- -ctt}
'aLfacf
@ - I
in thepresertceof aqueousBr, to form a
nergies.Explain
yourchoice, includingany
ffi-*re | ,E
-)
1-(;trq]
aT
. /<1.-(t\
rr'^ qa{jivz
sI
- Provide the
missingreactant,missingreagent(s),or majorproduct(s)for thefollowingreactions.
Be sureto indicate
stereochemistrywhereappropriate.If no reactionoccurs,w te NR. Pleasebox
yourfinal
answeml [ points]
n2'
,
Lindlar'scatalyst
01
HO
a)
HBr
t.
eH,'1-HF
2.+ltA2,
OA'
,, \ _ ,f
Hsso4,
H2o
-----trFb;-
e)
-^-Zn
(wrcn^ic
- Proposea multistepsynthesis
for thetwo moleculesshown belowfrom acetylene
(HC=CH)andany
othernecessaryreagentsor compoundswith
four carbons or less.Clearlyshowthereactants,
reagents.andproduclsfor eaghlea!1ig!-StlEp.0 pointsj
--
x+
=;a
F
=+Y
rcko
Y
(.*:
-=)
l, N4l.j+\z
t
bi
+1-=-+'l
l. NaNllz Y
------;'
J-=-
--l
L;,s'tt
- |
|
wl"
r.ho
^.
x
-a@
L.>
rzho
-z-..--\za?
+ ..':..-.-
\
--".,--\x
=e
l. N4tJH'
4-2'N
:---:---:"--,
.--.-
l
"'-'"'t2l
l, Brt3.l.}tF
l-(r )
\o,/
'''-/
4' fuor, oH-
q-=--A
l''!aN{z
'
--^-;.
LHE6.{.=
*-.2r,^-
-r
r n-
e.__--,...FY
f.i,u_
o
,*
ttAu
,r-...a^..f
I
-.'
- a) Drawa reasonablemechanism
usingcuryedarrowsthatcanaccountfor theformationofthe two
z-1r1.',-..tPH
(%-)
DH
Jbi++
l\l
?f'+* R'j-"- ?Q;-o
- Dmw oneenergydiagram
for theformationof thetwo productsfoffid in thehydrobromination
reactionbelow. You
may assumetheoverallreactionis exothermic.Includethestructureof any
p,
)^
fl4cbo-r
f-o{'Y.ss
.3r
this reaction.Usemechanismarrowsto showhowthe
,---€t
P--
/'
!t
--H
I
\ te
ff")
9n'" 1
fY laa
J
'H
/(lso
rereactionwhen l-methylcyclohexeneis treatedwith
m borohydride.
,_-^.__fcr-t
t)
- [6 points] a) Drawthemajorproduct(s)
of the reactionof I butynewithone equivalentof Brr.
T'I
t
b) Dmw thekgy intermediate(s)
involvedin thefl$llstep of this reaction
(reaction with aqueous
mercuryacetate).Usemechanismarrorasto showhow theintermediate(s)is(are)formed.
volvedin b) Drawthekq intermediate(s)
in
intermediate(s)
is(are)fonned.
, /'-w'Bc
__+
[6 points]
a) Drawthe
majorprodl
aqueousmercury(ll)aceate
and
aY 1.Hq{oAc),
H,o
I ll
------::------:L:-
,,, 2. NABH
1l,.o"-l
r'/-l
I I/ /
-'->
/ a-f-?r-- /
i- )
J
--t
1 A*z I
/ a-r- |
/
-Au9-.q"
I
L .."*.
"
J
v.r
^g>q
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