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Friday, 18 September 2015

p-Methoxyacetophenone.....Cock can teach you NMR




will teach u nmr

  • Find the molecular weight from molecular ion in the mass spectrum
  • What functional groups are present from the IR ?
  • What do the peaks at 7-8 ppm in the H-nmr and at 120-180 ppm in the 13C-nmr reveal ?
  • Look at the integration in the H-nmr
  • Use the above to get the molecular formula (make sure it matches the MW)
  • Count the number of types of C in the 13 C-nmr. What does this tell you ?

  • (particularly those between 120-180ppm)
  • What hydrocarbon pieces the H-nmr indicate ?
  • Using the chemical shifts how are these pieces connected together ?
  • Symmetry ?













  • In the MS, the molecular ion occurs at m/z = 150 indicating the MW = 150 g / mol.
  • The IR shows an C=O (1680 cm-1) and possible C-O (1250-1000 cm-1) but no -OH or -NH  (around 3500 cm-1)
  • 13 C-nmr shows 6 types of C, including a C=O (aldehyde or ketone, 213 ppm), and 3 ArC (178, 143 and 126 ppm) plus 2 other hydrocarbon C (63 and 34 ppm)
  • H-nmr
  • d/ppm
    multiplicity
    integration
    assignment
    8.0
    doublet
    2
     2 x ArH
     7.0
    doublet
    2
     2 x ArH
    3.9
    singlet
    3
     isolated CHdeshielded, possibly by O
    2.6
    singlet
    3
     isolated CH3 slightly deshielded
  • The lack of a peak at about 9 ppm rules out an aldehyde and therefore suggests a ketone.
  • The peaks at 7-8 ppm suggests a para-disubstituted benzene
  • This gives the following pieces C6H4, C=O, and 2 different -CH3
  • Leads to a suggested molecular formula of C9H10O which gives a MW = 134 g / mol which is 16 short, suggesting an extra O, probably as part of -OCH3 (peak at 3.9 ppm)\
  • So, molecular formula of C9H10O2 which gives a MW = 150 g / mol and IHD = 6
  • The 13C C=O at 213 ppm is a little high for an ester, so the methoxy group is the second aromatic substituent.
  • This gives the structure as:
  • Checking the H-nmr, we can see the two uncoupled methyl groups, one deshielded by O, the other slightly deshielded by the C=O and the para-disubstituted benzene.

Cosy predict



SYNTHESIS..........http://www.oc-praktikum.de/nop/en/instructions/pdf/1035_en.pdf



Anisole + Acetic anhydride
Zeolith H-BEA 25
reacts to

p-Methoxyacetophenone + Acetic acid ; Side reactions



13C-NMR

13C NMR
13C-NMR: crude product
75.5 MHz, CDCl3, TMS
delta [ppm]assignment
25.98CH3 acetyl
55.15-O-CH3
113.43C3
130.09C1
130.29C2
163.25C4
196.34C=O
76.5-77.5CDCl3
120.8C4 (educt anisole)
129.5C3 (educt anisole)



13C NMR
13C-NMR: p-Methoxyacetophenone
75.5 MHz, CDCl3, TMS
interactive spectrum
delta [ppm]assignment
25.98CH3 acetyl
55.15-O-CH3
113.43C5
130.09C1
130.29C2
163.25C4
196.34C=O
76.5-77.5CDCl3
120.8C4 (educt anisole)
129.5C3 (educt anisole)



IR

IR
IR: p-Methoxyacetophenone
[KBr, T%, cm-1]
interactive spectrum
[cm-1]assignment
2964arom. C-H valence
2843aliph. C-H valence
1669C=O valence, ketone
1604arom. C=C valence

Operating scheme

Operating scheme


Equipment

Batch scale: 0.01 mol 0.1 mol Anisole
round bottom flask 50 mL round bottom flask 50 mL
reflux condenser reflux condenser
suction filter suction filter
suction flask suction flask
heatable magnetic stirrer with magnetic stir bar heatable magnetic stirrer with magnetic stir bar
rotary evaporator rotary evaporator
distillation apparatus distillation apparatus
oil bath oil bath


Cappadocia Turkey.



 

 

Cappadocia - Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Cappadocia
Jump to Turkish Cappadocia - [edit]. Following the Battle of Manzikert in 1071, various Turkish clans under the leadership of the Seljuks began settling in ...





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