Chem 235LL Synthesis of Acetaminophen Postlab

Names: _________________________________
Day and time of lab: ______________________________
1. In this experiment you performed a synthesis. In the space below, draw the reaction between p-
aminophenol and acetic anyhydride to yield acetaminophen using line angle structures. emember to
write the name of each compound under the structure as well as the molecular mass of each compound.
!. "ill out the table below.
#ompound $elting point
#rude acetaminophen
%ure acetaminophen
&iterature acetaminophen
'Note: to find the literature (alues of any organic compound, the website
www.webboo).nist.go(*chemistry can be useful. #lic) on +name, then enter the name
+-cetaminophen, in the box. .hen clic) +phase change data,, and the melting point is reported as
+.
fus
,, reported in /el(in. #on(ert that to centigrade and put that (alue in the box. .his is how all
literature (alues for melting points should be reported. I spectra can also be found on this site. If not,
the spectral database for organic compounds may also be used.
0. "ill out the table below. -ttach your I spectrum to this postlab and turn it in.
#ompound bond 1a(enumber 2cm
-1
3
%ure acetaminophen
&iterature acetaminophen
1
0. .his wee) in lab we used reflux for the first time. In the space below draw what the reflux
apparatus loo)s li)e, and be sure to label all parts.
4. #onsider the image you drew for answer 0, abo(e. In the space below, briefly describe how reflux
works. emember to address specific issues li)e sol(ent boiling point, e(aporation, and condensation.
-lso explain why chemists use reflux. 1hy is reflux a helpful techni5ue6 1hat would happen if we
couldn7t use reflux6
!
8. In addition to reflux we also used another techni5ue this wee) called recrystalli9ation. "or the
following 5uestions, refer to the graph of recrystalli9ation from your lab manual. In the space below,
draw the graph that represents the solubility (s. temperature cur(e, then answer the following
5uestions.
Draw cur(e here:
8a. Is line - a good sol(ent for recrystalli9ation6 2circle one: yes * no 3
:riefly explain your answer.
8b. Is line D a good sol(ent for recrystalli9ation6 2circle one: yes * no3
:riefly explain your answer.
8c. Is line # a good sol(ent for recrystalli9ation6 2circle one: yes * no3
:riefly explain your answer.
0
;. #alculate your percent reco(ery and percent yield. emember to show all all wor) and to include
units for full credit.
<. In the space below, explain why your percent yield or percent reco(ery was low. If your percent
yield was not at least 8=> or your percent reco(ery was below 8=>, explain why. emember to use
specific claims such as +I used too much sol(ent during recrystalli9ation,. ?imply saying +human
error, is not a sufficient explanation of your results.
4
@. -naly9e your I data. #ompare pea)s that are present in your experimentally generated I
spectrum to those of the literature (alue. -re the same functional groups present6 -re the pea)s at the
same location 2i.e. wa(enumber3, and are they similar in intensity and shape6 1hat can you conclude
about the success of your experiment from your I data alone6 Does the I spectrum seem to indicate
a successful experiment6
8