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@
University of Jordan

Chemistry Department

zt iJt

Organic Chern 233

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...\... .a..,-sr

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-.eJ,

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Exam

pjr

....,......*.re.y4.t..

1) Give a,correct naqe for each of the

H3c-cH-cH2-?H-gH3
.H. ..:.,i*r,.".x 13fi.nf+ n ::2:. e
Br

,).,.roH

6l8l20ts

Il

nnpounds: [4 x

".-1..d..g,*...

plr

1.5 points]

CH3CH2GH2-O-CH2CH3

ffio

.,...S,rh.$..tr..-?.u\.s,..t.bsfr . ...... .

1...

'\rr'

L-l \t)u

...

g.

=..n.i.t

tI t/ghen e

2) Provide an answer for each of the foltrowing : [3 x2 points]

a) The transition state for the following reaction.
rrl

H"C-Br + SH +

b)

*/

t*

A diastereomer of the following compound.

.!, ru
H3C--,

.t

Ci

,*-f*i

l{)

Ass'uming that the observed rotation of a solution of

mL solvent was
rneasured using a tube which is
1s-ecjfi;curc.r:ffiolatiofi*try compound [o] in degrees.

{,

W*

rx\J-6(
l1

l-

Cx L

r Ll '
a.l + lo

(r-\
3) Circle the correct answer:

[12

1.5

uh,

cu,

'--]-u,.
cH.r

t'9n'$

c)

9."4t*.Br

$/,

-1*v"
*iArY

ficvw--+

\Os";

f (S)-!-bromobutane in 50
calculate the

'*L
m

r/(L)

points]

'rThe compound which has Zjconfiguration.

*"2

-1

.zf

xThe maxirnum number of possible stereoisorners of the following

CH=C

H--j*oH

*--E

* H--r-oit
Oo no-f-H
CH2OH

(a)

sixtesn

(b) six

@i

(c) four

q,The siructure rvith

{.lt)-configuration. (atomic mass:

C:l

=14, O:16, Br:80)

=<

jlt*c
'?6

CHs

Lt

(a) .
aut CH"CH.
ll

(c) Bri-Br
I

(d)

cH2cH3

t9-o

*The

@l
,4/

*crrcH.

tGl

* The hvdrogen halide (HX)

\
H"C-'C-OH
-/

__

reaction. :"

HeC..

U
//\
I t3u

HCi

(d)constitutionalisomers

w-hich reacts fqrtqul in the follorx,'ing

F1at.

(a)

1"1"nupffi
Lrx

(a) ide ntical

g.g-\g_y

H-X
:-,/ --.3-

Hsc

(b)

rmr

(c)

The strongesr ry4]eopbilg.

(a)
(b) F-

H:O

HI

(d) I-IF

(c) Ho-

(d) H2s

CH.

(d)

t-

H3c*c-ct

HK
x

The reagent,ivhich acc omplishe s the foll

(a)

Ne 66)crc,
v__--_i H-

(c)

ora,

inS

Qq;

:r-{zSo+

fo rm

(d)

ation)

HBr

(e) rr:O

*The following compounds have almost the same molecglar weights. which one of them
has the

SeEslpdilinryoint?

(t?"r,.

cH3cH?ocH2clll
-,*F

t'--u

structures.

f."-i-,,(,
' cH2cH3

tween

?t*'-

(c) CH3OCH20CH3

(d) CHsCH'CH2CH'CH1

xThe ggeg_t which accompiishes the foilowing transtbmation.

.-^\--CH2-OH
ll=!l=

(,
(a)

Fi2Soa

/^'-...-Ci,2-Cl

--_*

@ socrz

LJ

(c)

Ctz

(d)

pCC

(e) NaCl

xThe order of
&g1qg4iq&g4!gy of the following compounds.

oH

oH

'\'AA.\*
Y" V U
ir.l

?"

cHs
/w,
A,/BCD

@nrcrr{ro

--7./

* l'he alcohols which

H,.roH

(l

g;<->A>D
r, .- >

&)D>c>A>B (c)A>B>D>c (d)c>A>B>D

undergoes

a*ylgjg
-

with

/=--\
L;
H2SooQrr9 ur

_e

*C

\\'1,
4)

,/a

Show:

with equations how to synthesize the follorving

o\+

f --ol

f-)*o-cH2cH2cH3

>

l\

.oH

from a

s.[2x3pi-rints]

;D
=-,

suitabreffirroff"

B.

a\ , 1-\*,
?"* 4^ cr'" n^of!=
\--/-on

-------+

(}"

\-J

\*a

sctlz-c

H1

F-

/2

5) Give the major product(s) ot'the following reactions..

$r

$r

(He?
t-b
<

C$:

*t'

H3C-CH2-C1 + t"l3C*C:C\-.-.-..-

\--=-,------J

--+'

eH-l -Ctf z - c

cHt
l
-:- C .- C\lzCH,

'

Q\:

\
CH"
r r 6n
Y-3
H2SOa
L\-c_Cz(Hz
' ) -'H3C-+-CH2CH3
s*;.1
-l

.3' oH

Ituj
-_->
^..,-"
Qetr-

Wtin"-

ff

c\\*

,"{
5".1
A
ry"1
l

-rr-

\^iY'gr'

ot\

oHttnl
+3Brz

tHrc
0
-*u\2\'$r
$f
a(""o*
-1.s
cH,ctcurc-rf
\,/
r;\r
dYi'rq"'-'
l

\zL

o$

CH"

t"

HI

-+

cH3cH2-o-cH-cHs
.?o

(HucHtc

.,Hr -

L*cl\c

.SH

CH"

t'

CHICH;_-.i-Cl

i,

--_-.-)>

zo

H
ctA},

CH.

cH3oH

cH3cH2--+-CI

_._->

fiLo

nrc$r,

e Hs--l-

.*,"+.)
t\

1)

Mg I ether

____->

r \\ti-\'
mechanism:6
(show

o,,<-.-.(}-o

2) H2O

{\-J )-or+

CrO3

----------->
H+

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