Experiment 8

ORGANIC CHEMISTRY CHEMISTRY FOR TECHNOLOGY CHM 412 EXPERIMENT 8:

PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL

 NAME:

MARIAM HANANI ISMAIL

STUDENT ID:

2014827564

GROUP:

ED2604A

DATE OF EXPERIMENT:

10TH MAY 2016

DATE OF SUBMISSON:

17TH MAY 2016

INSTRUCTOR’S NAME:

MADAM FARIDAHANIM MOHD AAFAR  

EXPERIMENT 8 PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL

Pre lab assignment 1. Find te densit! re"eren$e's(.

"#r

$!$l#e%an#l

and

$!l#e%ene.

&tate

te

)ensit! #" $!$l#e%an#l * +.,-/ g0ml Obtained "r#m tts200en.3i4iedia.#rg03i4i0C!$l#e%an#l )ensit! #" $!$l#e%ene * +.5586 g0ml Obtained "r#m tts200en.3i4iedia.#rg03i4i0C!$l#e%ene

. &#3 te $al$7lati#n "#r te mass and m#les "#r + ml #" $!$l#e%an#l. '4 marks( Mass #" $!$l#e%an#l * +.,-/ g0ml X + ml * 1,./8 g M#lar mass * -'1.+1(  1'1(  1- * 1++.168 g0m#l N#. #" m#l * 1,./8 g 0 1++.168 g0m#l * +.1, m#l

Apparatus  Term#meter 91 still ead 91 $#ndenser 9 1 r#7nd b#tt#m :as4 '6+ml( 9 1 re$ei;ing :as4 '6+ ml( 91 r7bber #ses 9  $#ni$al :as4s '16+96+ ml( 9 adaters < deending #n te set a;ailable ret#rt stands 9  $ gra;it! "7nnel 91 3ater bat searat#r! "7nnel and st#er;'16+ml( 91 set test t7be 9 1 Chemicals C!$l#e%an#l 86= #s#ri$ a$id s#di7m $l#ride s#lid 1+= s#di7m $arb#nate s#l7ti#n an!dr#7s magnesi7m s7l"ate b#iling $is i$e $7bes. 19= >MnO/ s#l7ti#n Procedure 1. . ?. /. 6.

A simle distillati#n aarat7s 3as set 7. Ar#7nd 1+.6ml #" 86= #s#ri$ a$id 3as added in a r#7nd b#tt#m :as4. + ml #" $!$l#e%an#l and a "e3 b#iling $is 3as als# added in. Te rea$ti#n mi%t7re 3as distilled. Te re$ei;ing :as4 3as immersed 7 t# its ne$4 in an i$e bat t# a;#id l#ss #" an! r#d7$t 'b.. 8? C(. Te distillati#n :as4 3as eated $are"7ll! s# tat a stead! distillati#n rate is #btained. Te temerat7re #" te distilling ;a#rs 3as n#t all#3ed t# e%$eed 1+? C. Te rea$ti#n mi%t7re 3as st# eated 3en #nl! a "e3 ml #"  li@7id remain in te distilling :as4 #r 3en te ;a#rs e%$eed 1+? C. Te distillate 3as sat7rated b! adding s#lid s#di7m $l#ride #rti#n 3ise 3it s3irling. Te salt 3as st# added 3en it is n#t diss#l;ed an!m#re. Te e%$ess s#di7m $l#ride 3as 4et t# a minim7m. °

-. 5.

°

°

8.

,.

An! a$id 3as ne7tralied b! adding B7st en#7g 1+= s#di7m $arb#nate 'NaCO?'a@(( s#l7ti#n t# te mi%t7re 3it s3irling t# ma4e te a@7e#7s la!er basi$ '7se bl7e litm7s aer t# te s#l7ti#n(. E;er! a "e3 dr#s #" NaCO?'a@( added te s#l7ti#n 3as tested b! 7tting a dr# #" te s#l7ti#n #n a bl7e litm7s aer 7ntil it te bl7e litm7s aer remained bl7e. 1+. Te mi%t7re trans"er t# a searat#r! "7nnel and te a@7e#7s la!er drained. Te a@7e#7s s#l7ti#n and te #rgani$ s#l7ti#n 3ere determined. 11. Te #rgani$ la!er 3as #7red int# an Erlenme!er0$#ni$al :as4 and dried it 3it B7st en#7g an!dr#7s magnesi7m s7l"ate. 1. Te r#d7$t 3as Dltered int# a $lean dr! r#7nd b#tt#m :as4 ;ia gra;it! Dltrati#n. 1?. Te dried $!$l#e%ene 3as redistilled. 1/. Te b#iling #int re$#rded and te ;#l7me #" te r#d7$t meas7red. 16. Te r#d7$t "#rm 3as tested 3it a "e3 dr#s #" >MnO/'a@( te $#l#7r $ange #bser;ed. Observations:

1! T"# $%#&' (")*(")'+$ &$+, -&* +.*#'/#, +./) /"# ')., )//) 3%&*! 2! T"# ,+*/+%%&/# -&* $)+.#, -+/" 1 &., & "&%3 )3 s#lid s#di7m $l#ride 7ntil a ! 4!

5!

6! 7!

small am#7nt #" 3ite re$iitate 3as de#sited at te b#tt#m. A"ter ? dr#s #" s#di7m bi$arb#nate te bl7e litm7s aer remains 7n$anged.  T3# la!er s#l7ti#ns 3ere "#rmed and 3en distilled 3ater 3as added t# ma4e s7re 3i$ #" te s#l7ti#n is #rgani$ s#l;ent 't#( #r a@7e#7s s#l;ent 'b#tt#m(. Te a@7e#7s s#l;ent in$rease in am#7nt 3en distilled 3ater is added. Te a@7e#7s la!er is distilled 3ater and te #rgani$ s#l;ent is $!$l#e%ene.  and al" sat7la #" an!dr#7s magnesi7m s7l"ate 3as added t# te $l#7d! $!$l#e%ene 7ntil n# m#re #il! la!er $an be seen at te s7r"a$e #" te $!$l#e%ene s#l7ti#n.  Te b#iling #int is /+#C and te ;#l7me #" te $lear s#l7ti#n #" te end r#d7$t is 8.6 ml.  Te $!$l#e%ene s#l7ti#n de$#l#ried te  dr#s #" M.O4&9 *)%/+).!

Results:

B)+%+. ()+./: /+#C ;)%# )3 /"# ('),$/: 8!5 % T"# $