Lab  4:  Extraction  of  Iodine  from  an  Aqueous  Solution  

Written  by  
Danielle  M.  Solano  &  Carl  Kemnitz  
Department  of  Chemistry  &  Biochemistry  
California  State  University,  Bakersfield  

Objectives  
By  the  end  of  this  laboratory,  you  should  have  developed  the  skills  to  do  the  following:  
• Correctly  perform  a  liquid-­‐liquid  extraction.  
• Identify  the  aqueous  layer  and  the  organic  layer  in  a  liquid-­‐liquid  extraction.  

Recommended  Resources  
• Handout  ~  Topic  4:  Writing  an  Organic  Chemistry  Lab  Report  
http://www.csub.edu/chemistry/organic/manual/Topic4_Report.pdf  
• Handout  ~  Topic  7:  Using  a  Pasteur  Pipet  
http://www.csub.edu/chemistry/organic/manual/Topic7_Pipet.pdf  
• Tutorial  ~  Introduction  to  Extraction  Tutorial  
https://www.youtube.com/playlist?list=PLC5C96C5188CC44CE  

Background  
Extraction  is  the  process  of  transferring  a  substance  to  a  solvent.  It  is  useful  for  separating  mixtures  
of   compounds   and   removing   impurities   from   products.   The   extractions   that   you   will   do   for   most  
labs  involve  colorless  substances.  Under  these  circumstances,  it  is  impossible  to  see  in  which  layer  
your  desired  substance  resides.  Before  you  begin  any  extraction  procedures  for  those  labs  it  will  be  
beneficial   to   try   it   first   with   a   colored   substance,   such   as   iodine,   so   you   can   visually   see   what  
happens   in   an   extraction.   In   this   lab,   you   and   a   partner   will   use   two   different   organic   solvents   to  
extract  iodine  from  water  and  compare  your  results.  Further,  you  will  compare  the  efficiency  of  a  
single,  large  volume  extraction  to  the  efficiency  of  three  smaller  volume  extractions.  

       

__________________________________________________________________________________________________________________
1  
 Lab  4:  Extraction  of  Iodine  from  an  Aqueous  Solution  

 
Iodine  is  more  soluble  in  organic  solvents  than  it  is  in  water.  You  will  be  extracting  iodine  from  an  
aqueous   solution   of   iodine   and   potassium   iodide.   The   iodine/potassium   iodide   solution   is   brown   in  
color,  whereas  iodine  by  itself  is  a  nice  violet  color.  
Some  examples  of  what  you  might  expect  to  see  during  the  course  of  your  extraction  are  shown  in  
the   pictures   on   the   previous   page.   Note   that   the   location   of   the   iodine   (top   layer   versus   bottom  
layer)   changes   based   on   the   density   of   the   organic   solvent.   Also,   note   the   differences   in   color   of   the  
layers  as  more  and  more  iodine  is  extracted.  Be  sure  to  pay  attention  to  and  record  these  types  of  
observations  during  the  course  of  your  experiment.  

Lab  Notebook  Preparation  

Before  coming  to  lab,  the  following  items  must  be  in  your  lab  notebook:  
1. Title  of  the  experiment  &  date  the  experiment  is  to  be  performed  
2. Densities  of  dichloromethane,  hexane,  and  water  
3. Identify  which  layer  will  be  on  top  in  each  type  of  extraction  
4. Your  initial  hypothesis  regarding  the  efficiency  of  single  versus  multiple  extractions  
5. Hazards  of  and  appropriate  precautions  for  the  safe  handling  of  hexane,  dichloromethane,  
and  iodine  
6. References  

Directions  
1. Before   you   begin   this   experiment,   formulate   a   hypothesis   regarding   the   efficiency   of   single  
versus  multiple  extractions.  Use  the  principles  of  extraction  and  the  partition  coefficient  when  
developing  your  hypothesis  and  decide  what  results  will  reinforce  or  contradict  the  hypothesis.  
2. Set  up  your  work  area  by  clamping  a  ring  clamp  that  will  hold  your  separatory  funnel,  ensure  
that   the   stopcock   and   stopper   fit   well   and   work   properly,   and   make   sure   that   the   stopcock   is  
closed  before  beginning.  
3. Find   a   partner   who   is   willing   to   conduct   the   same   experiment,   but   who   will   use   a   different  
organic  solvent.  Select  who  will  use  dichloromethane  and  who  will  use  hexane.  
4. You  will  each  perform  the  experiment  twice.  The  first  time  you  will  conduct  one  extraction  of  60  
mL,  and  the  second  time  you  will  conduct  three  extractions  of  20  mL  each  (60  mL  total).  
5. First,  conduct  the  single  extraction.  
a. Measure   out   20   mL   of   0.005   M   iodine/potassium   iodide   solution   using   a   graduated  
cylinder.  
b. Use  a  funnel  to  transfer  the  solution  to  your  separatory  funnel.  
c. In  a  fume  hood  or  under  a  snorkel,  measure  out  60  mL  of  your  organic  solvent  using  a  
graduated  cylinder.  
d. Carefully  add  the  organic  solvent  to  the  separatory  funnel  without  mixing.  Note  which  
layer  is  on  top  and  which  layer  is  on  the  bottom.  Record  any  observations.  

__________________________________________________________________________________________________________________
2  
 Lab  4:  Extraction  of  Iodine  from  an  Aqueous  Solution  

 
e. Stopper   the   separatory   funnel   and   shake   it   gently,   venting   frequently.   Continue   until  
there  is  no  more  color  change.  Note  how  long  it  took  to  reach  equilibrium.  Record  the  
colors  and  intensities  of  each  layer.  
f. Let   the   mixture   sit   in   the   ring   clamp   until   the   two   layers   have   fully   separated   then  
carefully  drain  off  the  bottom  layer  into  a  125  mL  Erlenmeyer  flask.  
g. Transfer   the   top   layer   to   another   125   mL   Erlenmeyer   flask.   Label   the   flasks   and  
compare  your  results  with  your  partner’s.  (Which  organic  layer  is  darker  in  color?  The  
dichloromethane  or  the  hexane?  Which  aqueous  layer  is  darker  in  color?)  
h. Save  the  flasks  so  you  can  compare  them  to  your  results  from  the  triple  extraction.  
6. Next,  conduct  the  triple  extraction.  
a. Measure   out   20   mL   of   0.005   M   iodine-­‐potassium   using   a   graduated   cylinder   (do   NOT  
reuse  the  iodine-­‐potassium  iodide  solution  from  the  single  extraction).    
b. Use  a  funnel  to  transfer  the  solution  to  your  separatory  funnel.    
c. In  a  fume  hood  or  under  a  snorkel,  measure  out  20  mL  of  your  organic  solvent  using  a  
graduated  cylinder.  
d. Carefully  add  the  organic  solvent  to  the  separatory  funnel  without  mixing.  Note  which  
layer  is  on  top  and  which  layer  is  on  the  bottom.  Record  any  observations.  
e. Stopper   the   separatory   funnel   and   shake   it   gently,   venting   frequently.   Continue   until  
there  is  no  more  color  change.  Note  how  long  it  took  to  reach  equilibrium.  Record  the  
colors  and  intensities  of  each  layer.  
f. Let   the   mixture   sit   in   the   ring   clamp   until   the   two   layers   have   fully   separated   then  
remove   the   organic   layer.   (Note:   This   process   will   differ   depending   on   which   solvent  
you  are  working  with.)  
g. Once   the   organic   layer   has   been   removed,   combine   another   20   mL   of   your   organic  
solvent   with   the   aqueous   layer.   Again,   stopper   the   funnel,   shake,   let   it   sit,   and   remove  
the  organic  layer.  
h. Combine  your  second  organic  layer  with  the  first  layer  you  removed.  
i. Once  the  organic  layer  has  been  removed,  combine  a  final  20  mL  of  your  organic  solvent  
with   the   aqueous   layer.   Again,   stopper   the   funnel,   shake,   let   it   sit,   and   remove   the  
organic  layer.  
j. Combine  your  third  organic  layer  with  the  first  two.  
7. Compare   your   results   with   your   partner’s.   (Which   organic   layer   is   darker   in   color?   The  
dichloromethane  or  the  hexane?  Which  aqueous  layer  is  darker  in  color?)    
8. Compare   the   results   from   the   single   extraction   with   the   results   from   the   triple   extraction.  
(Which  organic  layer  is  darker  in  color?  Which  aqueous  layer  is  darker  in  color?)  
9. Record   your   final   conclusions.   (Which   solvent   extracted   the   most   iodine?   Which   type   of  
extraction  removed  the  most  iodine?  Was  your  initial  hypothesis  correct?)  
10. If  time  allows  and  you  would  like  additional  practice,  you  may  repeat  the  experiment  with  the  
solvent  you  did  not  use.  

__________________________________________________________________________________________________________________
3  
 Lab  4:  Extraction  of  Iodine  from  an  Aqueous  Solution  

 
11. Dispose  of  all  waste  in  the  designated  waste  container.  

Reporting  your  Results  

Write  your  report  according  to  the  guidelines  described  in  “Topic  4:  Writing  an  Organic  Chemistry  
Lab  Report”.  Work  with  your  partner  on  this  report.  

References  &  Additional  Resources  

1. Lehman,   J.   W.   Operational   Organic   Chemistry:   A   Problem-­‐Solving   Approach   to   the   Laboratory  
Course,  3rd  ed.;  Prentice  Hall:  Upper  Saddle  River,  NJ,  1999;  pp  475.  
 

__________________________________________________________________________________________________________________
4