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 CH3 deshielded, 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

+

Zeolith H-BEA 25

+

; Side reactions

+ Zeolith H-BEA 25 + ; Side reactions 1H-NMR 1H-NMR: crude product 300 MHz, CDCl3 delta [ppm] mult. atoms assignment 2.54 s 3 H -C(=O)-CH3 3.85 s 3 H -OCH3 6.91 m (AA') 2 H 3-H 7.91 m (XX') 2 H 2-H 2.09 CH3 (acetic acid) 1H-NMR: p-Methoxyacetophenone 300 MHz, CDCl3 delta [ppm] mult. atoms assignment 2.54 s 3 H -C(=O)-CH3 3.85 s 3 H -OCH3 6.91 m (AA') 2 H 3-H 7.91 m (XX') 2 H 2-H 2.09 CH3 (acetic acid)

¹³C-NMR

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

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

IR

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

Equipment

Batch scale:

0.01 mol

0.1 mol

Anisole

	round bottom flask 50 mL			reflux condenser
	suction filter			suction flask
	heatable magnetic stirrer with magnetic stir bar			rotary evaporator
	distillation apparatus			oil bath

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  Mt. Erciyes (3916 m), the highest mountain in Cappadocia
  
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  Göreme
  
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  Göreme in winter
  
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  Kaymakli underground city
  

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