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Write-up procedure:
1. Determine molecular formula from elemental analysis.
2. Determine elements of unsaturation from molecular weight [EOU=1/2(2C+2-H)]
3. Show all work
4. Label important stretches in the NMR and IR
5. Determine the structure
Experiment 1 post lab due in two weeks(week of Feb 6th-10th)
Example 1:MW: 88.1; BP: 73-76 °C/12 mmHg(lit.), Elemental Composition: C 54.53% H 9.15%
Example 2:MW: 169.22; BP: 302 oC, MP 52-54 oC; Elemental Composition: C 85.17% H 6.55% N 8.28%
NMR Signals
• The number of signals shows how many different kinds of protons are present.
• The location of the signals shows how shielded or deshielded the proton is.
• The intensity of the signal shows the number of protons of that type.
• Signal splitting shows the number of protons on adjacent atoms.
The NMR Graph
Chapter 13 8
Tetramethylsilane
• TMS is added to the sample.• Since silicon is less electronegative
than carbon, TMS protons are highly shielded. Signal defined as zero.
• Organic protons absorb downfield (to the left) of the TMS signal.
=>
Si
CH3
CH3
CH3
H3C
Chapter 13 9
Chemical Shift
• Measured in parts per million.
• Ratio of shift downfield from TMS (Hz) to total spectrometer frequency (Hz).
• Same value for 60, 100, or 300 MHz machine.
• Called the delta scale. =>
Chapter 13 10
Delta Scale
=>
Chapter 13 11
Location of Signals
• More electronegative atoms deshield more and give larger shift values.
• Effect decreases with distance.
• Additional electronegative atoms cause increase in chemical shift. =>
Chapter 13 12
Typical Values
=>
C5H10O
Example 3:MW: 108.14; BP: 202 oC, MP 32-34 oC; Elemental Composition: C 77.75% H 7.46%
Example 4:MW: 108.14; BP: 203 oC, MP 8-10 oC; Elemental Composition: C 77.75% H 7.46%