1. Using Proton NMR

2. How many Proton environments?

3. How many Proton environments?

4. How many Proton environments?

5. How many Proton environments?

6. Proton NMR Spectra Number of environments = number of peaks
Number of protons in environment = relative peak area (integral)
Number of protons on neighbouring carbon = splitting pattern (eg. doublet, triplet)
Type of proton environment = chemical shift (compare with datasheet)

7. Doublet
1H – NMR C2 H4 O
Quartet
Integral

8. Ethanal
2.2 ppm
9.8 ppm

9. Quartet
1H – NMR C3H8O
Singlet
Septet (7)
Integral

10. 1.2ppm
2-propanol
2.2ppm
4.0 ppm

11. Singlet
1H – NMR C4H8O2
Triplet
Quartet
Integral

12. 2.0ppm
Ethyl ethanoate
1.3ppm
4.1 ppm

13. Draw a Proton NMR to represent 1-Bromopropane – label with chemical shift, splitting pattern and relative integration

14. Draw a Proton NMR to represent 1-Bromopropane

15. Draw a Proton NMR to represent Butanoic acid – label with chemical shift, splitting pattern and relative integration

16. Draw a Proton NMR to represent Butanoic acid

17. Sketch the 1H NMR spectrum of compound X (see right) and label the relative peak areas. Label any peaks that would be lost from the spectrum on shaking with D2O.
[4]

18. 2 proton peak at δ = 3. 3-4. 3 – singlet (-CH2-)
2 proton peak at δ = – singlet (-CH2-) proton peak at δ = – singlet (-OH) proton peak at δ = – singlet (-COOH) 1 (ranges of chemical shift (δ) values taken from data sheet) • penalise each error once only • ignore peak areas/heights unless incorrectly labelled Labelled diagram of the structure of G proposed by the student may be used to provide evidence for the positioning of peaks on the sketched spectrum. Both OH and COOH protons disappear on shaking with D2O