3. Cycloaddition Product-NMR Analysis/Prediction a. Shown below are the two endo

Question

3. Cycloaddition Product-NMR Analysis/Prediction a. Shown below are the two endo cycloaddition products for this reaction, which are the two most likely products of this reaction. Predict the requested NMR data for each possible product. Structure A: End Structure B: Middle Number of total 13C NMR peaks? Above 100 ppm? Below 100 ppm? In the DEPT spectra: DEPT 90? Number of total 13C NMR peaks? Above 100 ppm? Below 100 ppm? In the DEPT spectra: DEPT 90? Pointed up in DEPT 135? Pointed up in DEPT 135? Pointed down in DEPT 135? Pointed down in DEPT 135? Number of total 'H NMR peakS? Number of total 'H NMR peakS? Above 5 ppm? Below 5 ppm? With multiplicity of: Singlet? Doublet? Above 5 ppm? Below 5 ppm? With multiplicity of: Singlet? Doublet? Triplet? Triplet?

Explanation / Answer

Structure with End-Ring:

a) Number of total 13C NMR peaks = 9

b) Above 100 ppm - there are 7 peaks (signals)

c) Below 100 ppm - there are 2 peaks

d) In the DEPT spectra: DEPT 90 - only the peaks corresponding to CH will appear = 6

e) Pointed up in DEPT 135 - The peaks corresponding to CH and CH3 will be pointed up in DEPT 135 = 6

f) Pointed down in DEPT 135 - The peaks corresponding to CH2 will be pointed down in DEPT 135 = 0

g) Number of total 1H NMR peaks = 6

h) Above 5 ppm - there are 4 peaks (signals)

i) Below 5 ppm - there are 2 peaks (signals)

j) With a multiplicity of singlet = 1

k) With a multiplicity of doublet = 4

l) With a multiplicity of triplet = 1

Structure with Middle-Ring:

a) Number of total 13C NMR peaks = 6

b) Above 100 ppm - there are 4 peaks (signals)

c) Below 100 ppm - there are 2 peaks

d) In the DEPT spectra: DEPT 90 - only the peaks corresponding to CH will appear = 4

e) Pointed up in DEPT 135 - The peaks corresponding to CH and CH3 will be pointed up in DEPT 135 = 4

f) Pointed down in DEPT 135 - The peaks corresponding to CH2 will be pointed down in DEPT 135 = 0

g) Number of total 1H NMR peaks = 4

h) Above 5 ppm - there are 2 peaks (signals)

i) Below 5 ppm - there are 2 peaks (signals)

j) With a multiplicity of singlet = 0

k) With a multiplicity of doublet = 4

l) With a multiplicity of triplet = 0

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