LABREPORT:EXPERIMENT8.

LIQUIDSPECTROSCOPICUNKNOWN
Name:
HanTaub

OrganicChemistry205

Date:12/1/15
UnknownNumber:C25
1.UnknownNameandStructure(ChemBioDraw):

2.AnalysisofData:Explainhowallofthedata(1HNMR,13CNMR,IR,MS,CHanalysis)
supportstheassignedstructure.Showthecalculationsforhowyoudeterminedyourmolecular
formula.Ifthedataisambiguousdescribetheinconsistenciesandpossibleexplanationsfor
theseresults.Includecopiesofyourspectraanddatawiththereport.
Theanswerstothisquestionshouldbetypedonaseparatepageandattachedtothisform
alongwithyourspectra.
HonorPledge:IaffirmthatIhaveadheredtotheHonorCodeonthisassignment.

MassSpectrometryAnalysis:
C=64.82%,H=13.60%
M=73.15m/z
C=(73.15m/z)*(.6482)/(12.01g/mol)=3.954
H=(73.15m/z)*(.1360)/(1.01g/mol)=9.8510
73.15(4*12.01g/mol+10*1.01g/mol)=15.0116g/mol=oxygen
FORMULA=C4H10O
IRSpectrumAnalysis:
Broadbandfrom30003500cm1suggestsanROHgroup.
1

HNMRAnalysis:

Tripletat0.90ppmsuggestsCH3group.
Sextupletat1.35ppmsuggestsCH2group.
Singletat1.45ppmsuggestsOHgroup.
Quintupletat1.55ppmsuggestsCH2group.
Tripletat3.60ppmsuggestsCH2groupadjacenttoOH.
13

CNMRAnalysis:

Peakat13.821isaCH3group.
Peaksat18.859and34.797areCH2groups.
Peakat62.603isaCH2groupadjacenttoOH.

LABREPORT:EXPERIMENT9ELECTROPHILICAROMATICSUBSTITUTION
Name:
HanTaub

LabDay:Thursday

Date:

12/1/15

OrganicChemistry205

ReactionEquation(ChemBioDrawstructuralformulasfororganiccompounds):

Reactants
1.MolecularMassesofreactants:
a.Vanillin:

152.15g/mol

b.PotassiumIodide:

166.00g/mol

c.Sodiumhypochlorite:
74.44g/mol

2.Amountofreactantsused(grams,moles)
a.Vanillin:

0.249g,0.00164mol

b.PotassiumIodide:

0.338g,0.00204mol

c.Sodiumhypochlorite:
.1575g,0.00203mol

(assumeNaOCl(aq)density=1g/mL)
d.Limitingreagent:

vanillin

Product
a.MolecularMassof5iodovanillin:

278.04g/mol

b.Isolatedmassof5iodovanillin(g,mol):

0.369g,0.00133mol

c.%Yieldof5iodovanillin:

81.10%

d.Meltingrangeofproduct:

179.8

C183.7C

Honor Pledge: I affirm that I have adhered to the Honor Code on this
assignment.

Questions:
1.

2. This iodination is directed by the strong activator OH. However, the para
position and one of the ortho positions are occupied by other groups, which
leaves only one location for the iodination to occur.