Transcript
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
1/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Purpose:'he purpose of this experiment is to synthesi(e an or)anic al*ene +ia ,ehy,ration of an or)anic alcohol usin) a
stron) aci, catalyst in an E1 elimination reaction. 'he i,entity of the final pro,uct will -e confirme, +ia
measurement of the refracti+e in,ex 0 spectroscopy an, a test for the presence of ,ou-le -on,s.
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
2/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
pproach:Determine the mass of cyclohexanol rea)ent C2"1!34 -y wei)hin). Compute the mass of 5.56 Phosphoric aci,
catalyst "!P3&4. Compute the moles of each Cyclohexanol an, 5.56 "!P3&. Set up the -alance, stoichiometric
e7uation an, ,etermine the molar ratio of the rea)ents. Determine the limitin) rea)ent. Calculate the theoretical
yiel, for the synthesis. ssem-le simple ,istillation apparatus an, initiate the reaction. Distill the rea)ents at
895oC. Saturate the ,istillate with soli, so,ium chlori,e. ,, 1%6 a7ueous So,ium car-onate an, test with litmu
paper until the ,istillate is -asic p";/-lue test result4.
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H 1 #ass of Cyclohexanol 0esults Bn* No.
#aterials E7uipment#ass Cyclohexanol
#ass +ial 1!.2!5)
#ass +ial I sample !1.15&)
#ass sample !1.15&?1!.2!5 J .5!)
ial
Cyclohexanol approx.
1%m@4
Electronic
-alance L%.%%14 Calculator
Desc:
'are the -alance
Determine the mass of rea)ent in +ial.
Empty the +ial into the ,istillation flas*.
Determine the mass of the +ial.
Calculate the mass of the rea)ent.
E7uation Setup:
#ass rea)ent )4 J #ass rea)entI+ial )4 M #ass
+ial )4
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H ! #ass 56 Phosphoric aci, 0esults
#aterials E7uipment#ass 5.56 "$P3&
ol m@4 !.&m@
Density )/m@4 1.;1)/m@
6 Composition 5.56
1.&m@ 1.;1 %.55 J $.51)
ial 5.56
Phosphoric aci,
approx. !.5 m@4
Ara,uate,
cylin,er Calculator
Desc:
Calculate the mass of the rea)ent from
the +olume an, the ,ensity
E7uation Setup:
#ass J Density )/m@4 ol m@4 6 comp.
5.564
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H $ #oles 0ea)ents 0esults
#aterials E7uipment#oles Cyclohexanol
#ass )4 .5!)
#.
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H & #olar 0atio: Synthesis of Cyclohexene
Stoichiometric >alance, E7uation Bse Structural ormulas4
#olar 0atio
1 mol Cyclohexanol 1 mol Cyclohexene 1 : 1
0eaction #echanism
1. Protonation of "y,roxyl )roup -y
stron) aci, sli)htly exothermic4
!. ormation of Car-ocation/stron)
electrophile -y loss of an "!3
molecule slow/rate ,eterminin)
step? hi)hly en,othermic4
$. "!3 acts as nucleophile -ase4 an,
a-stracts a -eta proton from the
car-ocation to form the al*ene fast
step ?exothermic4
3+erall reaction is sli)htly
en,othermic. Bn,er aci,ic
con,itions at hi)h temp.
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H5 @imitin) 0ea)ent 0esults
#aterials E7uipment#olar 0atio
Stoichiometric 1:1
Experimental N/
3-ser+ations:
>ecause cyclohexanol is the only rea)ent
in the synthesis "$P3&only ser+es as a catalyst
an, proton ,onor in the reaction is not a true
rea)ent4 cyclohexanol is limitin) an, the molesof cyclohexanol are e7ui+alent to the theoretical
yiel, of cyclohexene.
Calculator
Desc:
Compare the -alance, stoichiometric
molar ratio for the synthesis reaction to the
experimental molar ratio
f the experimental ratio is less than the
stoichiometric ratio the rea)ent in the
numerator is limitin)
'he limitin) rea)ent ,etermine the
maximum 7uantity of pro,uct that can -e
pro,uce, in a reaction
E7uation Setup:
Cyclohexanol I "!P3& O Cyclohexene
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H 2 'heoretical iel, 0esults
#aterials E7uipment'heoretical eil,
Cyclohexanolol mol4 %.%51&5mol
Cyclohexene mol4 1
#.
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H ; 'heoretical iel, Summary 'a-le 0esults
Desc: Cyclohexanol is the only rea)ent in the
synthesis reaction therefore the moles of
cyclohexene expecte, is e7ual to the moles of
cyclohexanol use,.
.
I 1 "!31 CyclohexeneI 1 "$P3&1 Cyclohexanol>alance,
E7uation
1.%!)/mol!.1&$)/mol92.995)/mol1%%.15)/mol#olecular
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H Simple Distillation 0esults
#aterials E7uipment3-ser+ations:
Solution -e)an to -oil aroun, %oC. Distillation -e)an aroun, 9%oC an,
remaine, at this temperature for the ma=ority o
the ,istillation process.
Distillation was stoppe, when thetemperature rose to 95oC remaine, there
-riefly an, rapi,ly rose a-o+e 1%%oC.
5.56
Phosphoric aci,
approx. !.5 m@4 Cyclohexanol
approx. 1%m@4 'eflon -oilin)
chip ce water -ath
5%m@
Distillation flas* !5m@
recei+in) flas* Alass
funnel "ot plate San, -ath 'hermomet
er with a,apter Con,enser Distillation
hea, luminum
plate
luminumfoil
Desc:
ssem-le ,istillation apparatus.
Place approx. 1%m@ Cyclohexanol an,
approx. !.5 m@ 5.56 "!P3& into a 5%m@
,istillation flas* usin) a )lass funnel.
Swirl )ently to com-ine rea)ents.
,, -oilin) Chip
Place !5m@ recei+in) flas* in ice water
-ath >e)in water circulation
"eat mixture until ,istillation -e)ins
approx. 95?1%%oC4
Collect ,istillate until the mixture no
lon)er -u--les or when the temperature
increases rapi,ly past 1%%oC.
Do not ,istill to ,ryness.
E7uation Setup:
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
11/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H9 #easure p" 0esults
#aterials E7uipment3-ser+ations:
Bpon the a,,ition of 1%6 So,ium
Car-onate a7 to the experimental solution the
litmus test turne, -lue in,icatin) that the
solution is now -asic p";4.
Complete neutrali(ation re7uire, the
a,,ition of se+eral m@ of NaC3$
So,ium
Chlori,e 1%6 So,ium
Car-onate a7 @itmus Paper
!5m@
recei+in) flas* with
,istillate Plastic
pipet
Desc: 0emo+e !5m@ recei+in) flas* from the
,istillation apparatus
Saturate the ,istillate with NaCl -y
a,,in) small amounts an, swirlin) the flas*
)ently
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H 1% @i7ui,/@i7ui, Extraction 0esults
#aterials E7uipment3-ser+ations:
'he -ottom a7ueous layer was much
lar)er than the top or)anic layer containin) the
cyclohexene pro,uct.
Neutrali(e,
,istillate
!5m@
Sepratory funnel Alass
funnel Alass
stopper
1%%m@>ea*er
5%m@
Erlenmeyer flas*
Desc:
Decant the neutrali(e, ,istillate into a
sepratory funnel usin) a )lass funnel
0emo+e )lass funnel an, stopper the
sepratory funnel
llow ,istillate to settle an, separate into
layers. Drain -ottom a7ueous layer into a
1%%m@ waste -ea*er
'hrou)h the top of the sepratory funnel
pour the or)anic layer into a clean ,ry 5%m@
Erlenmeyer flas*.
E7uation Setup:
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H 11 Dry Pro,uct 0esults
#aterials E7uipment3-ser+ations:
Pro,uct chan)e, from clou,y to clear
when nhy,rous So,ium sulfate was a,,e,.
nhy,rous
So,ium Sulfate
5%m@
>ea*er with
Cyclohexene
Desc:
,, small amounts of nhy,rous
So,ium Sulfate swirlin) occasionally until the
pro,uct appears clear may re7uire 1%?15minutes to achie+e clearness4
E7uation Setup:
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H1! Simple ,istillation 0esults
#aterials E7uipment3-ser+ations:
Secon, ,istillation was not carrie, out a
the +olume of pro,uct synthesi(e, was too smal
an, ris*e, total e+aporation.
Drie,
Cyclohexanol 'eflon -oilin)
chip ce -ath
!5m@
Distillation flas* !5m@
recei+in) flas* Alass
funnel "ot plate San, -ath 'hermomet
er with a,apter Con,enser Distillation
hea, luminum
plate luminum
foil ial with
cap
Desc:
Clean ,ry an, reassem-le the
,istillation apparatus.
Slowly ,ecant the ,rie, pro,uct from the
5%m@ -ea*er into a !5m@ ,istillation flas*
Place the !5m@ recei+in) flas* in an ice
water -ath.
>e)in water flow throu)h the con,enser.
"eat the sample an, collect ,istillate
-etween %?2oC !?$ ,e)rees -efore an, after
the -oilin) point of the compoun,4
E7uation Setup:
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H1$ #ass Cyclohexene 0esults
#aterials E7uipment#ass Cyclohexene
#ass +ial 1!.2!2)
#ass +ial I sample 1&.!&)
#ass sample 1&.!& M 1!.2!2 1.2!!)
Cyclohexanol Calculator Electronic
-alance L%.%%14 Alass
funnel
Desc: 'are the -alance.
Determine the mass of the empty +ial
with cap.
Dispense ,istillate into the +ial usin)
)lass funnel an, seal.
Determine the mass of the compoun, in
the +ial
E7uation Setup:
#ass rea)ent )4 J #ass rea)entI+ial )4 M #ass
+ial )4
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
17/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H 1& Percent iel, 0esults
#aterials E7uipmentPercent eil,
Experimental iel, 2.99&1)
'heoretical iel, 1.2!!)
1.2!! / 2.99&1 4 1%% J !$.196
Calculator
Desc:
Pro+i,es a measure of efficiency for the
reaction -y comparin) the ratio of experimental
pro,uct yiel,e, an, the theoretically expecte,
pro,uct yiel,s.
E7uation Setup:
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
18/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H 15 0efracti+e in,ex 0esults Bn* No.
#aterials E7uipment 0oom temperature: !$.%oC
Cyclohexene
1stND 1.&&5!
!n,ND 1.&&5
+) ND: 1.&&55
Cyclohexene
pro,uct 'issue lcohol Dropper
--e
refractometer L
%.%%%!4
Desc:
Note an, recor, the temperature of the
room
Carefully clean the prisms of the --e
refractometer with a tissue moistene, with
alcohol.
,, a small amount of the compoun,
-etween the prisms.
Aently close the prisms.
lip the switch on the left of the
instrument up to turn on the So,ium?D lamp
an, a,=ust it into position. Bse the a,=ustment *no- at the ri)ht of
the instrument so the crosshairs intersect with
the hori(ontal ,i+i,in) line of the +isual fiel,.
,=ust the ,rum *no- at the front of the
instrument to sharpen the hori(ontal line if
chromatic a-erration occurs.
Press ,own on the switch on the left of
the instrument to ,isplay the refracti+e in,ex
scale
0ea, an, recor, the refracti+e in,ex tofour ,ecimal places.
0epeat this measurement an, recor, a
secon, rea,in).
E7uation Setup:
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
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Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H 12 'emperature Correction actor 0esults
#aterials E7uipment0oom temp J !$.%oC
Cyclohexene
ND!%J ND
0m 'empI 0oom 'emp ? !%4 %.%%%&5
ND!% J 1.&&5 I !$?!%4 %.%%%&5
ND!% J 1.&&29
Calculator
Desc:
,=usts the measure, +alue of the
refracti+e in,ex ND4 o-taine, usin) the --e
refractometer to stan,ar, temperature of !%oC.
0efracti+e in,ex is -oth wa+elen)th an,
temperature ,epen,ent for a )i+en compoun,.
'emperature an, ,ensity are in+ersely
relate,.
Density an, the +elocity of li)ht are
in+ersely relate,.
s temperature increases ,ensity
,ecreases an, +elocity of li)ht increases.
0efracti+e in,ex ,ecreases as
temperature increases.
E7uation Setup:
0efracti+e n,ex n4 M Qthe ratio of the +elocity of
li)ht in the air to the +elocity of li)ht in the me,ium
-ein) measure,R Pa+ia pp&54
or temperatures !%oC a,, the temperature
correction factor
ND!%J ND
0m 'empI 0oom 'emp ? !%4 %.%%%&5
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
20/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H1; 0 Spectroscopy 0esults
#aterials E7uipment0 Spectral nalysis:
Saturate, l*ane C" stretch
C"!4$%%%cm?1
Bnsaturate, l*ene C" stretch $%%%cm1
C"!-en,in) a-sorption at 1&5%cm?1
0 potassium
-romi,e4 pellet chemwipe
0
Spectrometer
Desc:
Place 1?! ,rops of sample -etween ! salt
plates
Place salt plate san,wich in plate hol,er
an, inset into -eam slot of the 0 Spectrometer.
Chec* with professor to ma*e sure
-ac*)roun, has -een scanne,.
Select appropriate memory location T
or U4 Press scan -utton. #a*e sure the
num-er of scans in,icates &.
Press execute -utton.
f a-sorption ,oes not rea, properly
remo+e salt plate an, try a)ain usin) a smaller
amount of the un*nown sample.
0un an, recor, a secon, trial
Press plot -utton to pro,uce )raph.
0emo+e cell hol,er an, ,isassem-le the
apparatus. Clean the salt plate with acetone an, ,ry
with chem wipe
Place salt plates in ,esiccator to ,ry.
E7uation Setup:
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
21/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Proc H1 Dou-le >on, 'est 0esults
#aterials E7uipment3-ser+ations:
Due to the small +olume of ,istillate
collecte, only the >romine in #ethlyene
Chlori,e ,ou-le -on, test was carrie, out an,
compare, with the cyclohexanol rea)ent to
+erify the presence of ,ou-le -on,s.
>romine in #ethylene Chlori,e was
re,,ish -rown in color.
@ess than 1% ,rops were use, to perform
the test as the +olume of ,istillate was so small.
r in C"!Cl!,issipate,
in,icatin) the presence of ,ou-le -on,s.
romine in
#ethylene Chlori,e
solution 1!?
Dimethyloxyethane Potassium
perman)anate
& small test
tu-es 'est tu-e
rac* & ,roppers
Desc:
Bsin) a clean ,ropper place 5 ,rops of
Cyclohexanol into two small test tu-es
Bsin) a clean ,ropper place 5 ,rops of
Cyclohexene into two small test tu-es
,, 1% ,rops of >romine in #ethylene
Chlori,e solution to one of the test tu-escontainin) Cyclohexanol.
0epeat with one of the test tu-es
containin) Cyclohexene.
f the solution -ecomes colorless the re,
is ,ischar)e, from the solution4 the ,ou-le
-on, has -een -ro*en an, replace, -y two
-romine molecules.
'o the other two test tu-es a,, approx.
%.$m@ of 1!?Dimethyloxyethane.
,, 1% ,rops of Potassium
perman)anate to each of the two test tu-es.
f a -rown precipitate appears the
cyclohexene has -een oxi,i(e, ,ou-le -on,
-ro*en4 an, con+erte, to an alcohol an,
perman)anate has -een re,uce, to man)anese
,ioxi,e.
E7uation Setup:
>r!in #ethylene Chlori,e
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
22/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
K#n3&
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
23/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
Summary of 0esults:
'he mass of Cyclohexanol was .5! ). 'he mass of Phosphoric aci, was $.51). 'he moles of
Cyclohexanol use, were %.%51&5mol. 'he moles of Phosphoric aci, use, were %.%$21;mol. 'he molar
ratio of Cyclohexanol: Phosphoric aci, from the -alance, stoichiometric e7uation was 1:1. 'he theoretica
yiel, for the synthesis reaction was 2.99&1) of Cyclohexene an, 1.5$&$) of "!3. 'he mass of Cyclohexene
synthesi(e, was 1.2!!). 'he percent yiel, for the reaction was !$.196. 'he raw refracti+e in,ex of the
final pro,uct was 1.&&55D!$. 'he refracti+e in,ex +alue calculate, to correct for temperature was 1.&&29D
!
'he 0 spectrum o-taine, showe, the followin) principal a-sorptions: Saturate, al*ane C" stretch
$%%%cm?1 Bnsaturate, al*ene C" stretch $%%%cm?1 C"!-en,in) a-sorption at 1&5%cm?1 CJC al*ene
a-sorption at 125%cm?1
an, out of plane C" -en,in) at 1%%%?25%cm?1
. n a,,itional -roa, stron)a-sorption was shown aroun, $&%%cm?1. 'he >r!in #ethylene Chlori,e test was positi+e.
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
24/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
nalysis Conclusions:
n the synthesis of Cyclohexene is the only rea)ent. n the synthesis reaction the role of "!P3& alon)
with heat is merely to ser+e as a source of protons for the protonation of the hy,roxyl )roup of
Cyclohexanol an, to cataly(e the reaction not to ser+e as a true rea)ent. s such Cyclohexanol is the
limitin) rea)ent the theoretical yiel, of Cyclohexene in moles was e7ual to the num-er of moles of
Cyclohexanol use, an, a maximum pro,uct yiel, of 2.99&1) of Cyclohexene an, 1.5$&$) of "!3 was
anticipate,. 'he reaction was initiate, an, simple ,istillation was carrie, out. 'he reaction mixture
was ,istille, at 9%oC an, cease, when the temperature rose rapi,ly o+er this temperature. >ecause th
reaction is an e7uili-rium reaction heatin) the mixture shifts the e7uili-rium towar,s the formation o
the al*ene pro,uct.
'he ,istillate was then neutrali(e, -y the a,,ition of an a7ueous -ase 1%6 So,ium Car-onate4 until
the p" of the mixture was +erifie, as such -y @itmus test. NaCl was then a,,e, to the ,istillate to
re,uce the solu-ility of Cyclohexene in any remainin) aci, an, water -y?pro,ucts that mi)ht ha+e
-een co?,istille,. 'his cause, the ,istillate to separate into layers with the a7ueous phase settlin) to
the -ottom of the sepratory funnel an, the less ,ense cyclohexene pro,uct risin) to the top. 'he
or)anic layer was then ,rie, with nhy,rous So,ium Sulfate to remo+e resi,ual "!3 from the
pro,uct. lthou)h careful la-oratory practices were use, throu)hout this process the +olume of
pro,uct that resulte, after these proce,ures was +ery small 1.2!!) representin) !$.196 of the
theoretical yiel,4. n the interest of conser+in) what little pro,uct remaine, the secon, ,istillation wa
not performe, as ,istillin) such a small +olume of compoun, is more li*ely result in total e+aporation
rather than a si)nificant isolation of purifie, pro,uct.
0e)ar,less 0 spectrum for the pro,uct was o-taine, an, analy(e, to ,etermine if first ,istillation
resulte, in a pro,uct that was pure enou)h to carry out the remain,er of the experiment. 'he ma=ority
of spectrum a-sorptions were foun, +isually consistent with the a-sorptions shown for a stan,ar, 0
spectrum of Cyclohexene o-taine, from the SD>S we-site. 'he spectra for the pro,uct showe, a
-roa, stron) 3" a-sorption at $&%%cm?1that was not consistent with the stan,ar, spectrum. 'his
was li*ely ,ue to resi,ual "!3 or Cyclohexanol. 'his coul, -e controlle, for -y performin) the secon,
simple ,istillation proce,ure to further purify the pro,uct.
inally the compoun, was teste, with >r!in #ethylene Chlori,e. r! ,i, not persist in,icatin) the presence of ,ou-le -on,s. 'he secon, confirmatory testwith K#n3& was not carrie, out ,ue to the small +olume of pro,uct. Some of the potential errors of
this experiment inclu,e the thermal inefficiency of the ,istillation apparatus an, errore, temperature
rea,in)s of the thermometer. Bsin) fractional ,istillation rather than multiple simple ,istillations
coul, ai, in increasin) the yiel,. ,,itionally the yiel, coul, -e maximi(e, -y the a,,ition of a
compoun, with a hi)her -oilin) point such as toluene4 to help push more of the pro,uct towar,s the
recei+in) flas*. lthou)h this a,,s an a,,itional impurity to the reaction mixture more of the ,esire,
pro,uct woul, ,istill.
7/25/2019 Chem 315 -Lab 9 -Synth of Cyclohexene
25/25
Experiment: Date:
Synthesis of Cyclohexene 11/5/15
Name Partners Drawer No. Course / Section
Katheryn Soto N/ !1C"E#
$15/!%&
@iterature Summary Bn*nowns Synthesi(e, Compoun,s4
Bn*nown No.
CS No. 11%?$?
Name BPC4 Cyclohexene
Synonyms
'etrahy,ro-en(ene
#eltin) Point
oC4
@it ?1%$.5oC
Exp
@it
Exp
@it
Exp
@it
Exp
>oilin) Point
oC4
@it !.9oC
Exp
@it
Exp
@it
Exp
@it
Exp
0efracti+e n,ex nD
!%4@it 1.&&25
!%
Exp@itExp
@itExp
@itExp
Solu-ility
0el to
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