CHEM 4341/6371

Exam 4

NAME:

1. [20 points] Calculate the approximate chemical shifts of the circled nuclei in the following molecules. Show the equation that you
use.
O

CH 3
1

H chemical shift:

calculation:

OCH 3
1

13

C chemical shift:

calculation:

13

2. [10 points] Which hydrogen (Ha or Hb) appears at higher chemical shift in the 1H NMR spectrum? Justify your answer with
reference to a resonance structure that addresses the shielding of the nuclei.
OCH 3

H that appears at highest chemical shift?

Rationale:

3. [10 points] Determine the chemical shift (to two decimal places), multiplicity and coupling constant(s) (to nearest 1 Hz) of the
following multiplet, which was recorded on a 300 MHz instrument.

For questions 4 and 5 significant amounts of partial credit will be provided for analysis of data in the tables provided, including the
identification of structural fragments.
4. [40 points] Complete the analyses of TWO of compounds A-C, put a large X though the two pages of the problem that you do not
want to be graded.
5. [20 points] Complete the analyses of compound D.

Cl

Compound A
C10H12O2

Interpretation of 13C NMR data, including DEPT

Analysis of 1H NMR spectrum

/ ppm

Fragments

Structure

mult.

J / Hz

integral

assignment

Compound A
C10H12O2
Also shows a broad peak at approx 12.8 ppm

Compound B
C9H14O

Interpretation of 13C NMR data, including DEPT

Analysis of 1H NMR spectrum

/ ppm

Fragments

Structure

mult.

J / Hz

integral

assignment

Compound B
C9H14O

Compound C
C10H9N

Interpretation of 13C NMR data, including DEPT

Analysis of 1H NMR spectrum

/ ppm

Fragments

Structure

mult.

J / Hz

integral

assignment

Compound C
C10H9N

Compound D
C6H10O2

Interpretation of 13C NMR data, including DEPT

Analysis of 1H NMR spectrum

/ ppm

Fragments

Structure

mult.

J / Hz

integral

assignment

Compound D