Br R = H, CH3 B(OH)2 R' Pd(OAc)2, PPh3 aq Na₂CO3 n-PrOH R' = H, CH3, OCH 3

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Please explain why if the 13C & 1H NMR spectrum data below is the possible structure of known compound ' 1-(4'-methyl-[1,1'-biphenyl]-4-yl)ethanone'? (Suzuki Cross-Coupling)

1H NMR:

2.41 ppm, 3H, singlet, aromatic -CH3

2.64 ppm, 3H, singlet, ketone, -CH3

7.27-7.29 ppm, 2H,doublet, aromatic -CH

7.53-7.54 ppm, 2H,doublet, aromatic -CH

7.67-7.68 ppm, 2H,doublet, aromatic -CH

8.01-8.03 ppm, 2H,doublet, aromatic -CH

13C NMR

22 ppm, -CH3 attached to the aromatic ring

26 ppm, -CH3 attached to the ketone carbonyl

127 ppm, aromatic -CH

129 ppm, aromatic -CH

130.5 ppm, aromatic -CH

135 ppm, aromatic -CH

137 ppm, aromatic -CH

145 ppm, aromatic -CH

197 ppm, carbonyl carbon of ketone

IR:

A band at 3040 cm-1 is a stretching frequency of the C-H bond of the alkene.

A band at 1672 cm-1 is a stretching frequency of the -C=O bond of ketone (alpha beta unsaturated ketone).

A band at 1598 cm-1 is a stretching frequency of the C=C bond of the aromatic ring.

A band at 1391 and 1362 cm-1 is a bending frequency of the C-H bond of the alkane.

A band at 1260 and 1131 cm-1 is a bending frequency of the C=O bond of the ketone.

A band at 824 cm-1 is a bending frequency of the C-H bond of the aromatic ring the aromatic ring must be para-disubstituted.

B(OH)2
6.5
R
Br
R = H, CH3
Pd(OAc)2, PPh3
aq Na₂CO3
n-PrOH
R' = H, CH3, OCH 3
Transcribed Image Text:B(OH)2 6.5 R Br R = H, CH3 Pd(OAc)2, PPh3 aq Na₂CO3 n-PrOH R' = H, CH3, OCH 3
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