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For each compound shown below,(1) Sketch the 13C NMR

Chapter 18, Problem 41SP

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QUESTION:

For each compound shown below,

(1) Sketch the \({ }^{13} C\) NMR spectrum (totally decoupled, with a singlet for each type of carbon), showing approximate chemical shifts.

(2) Show the multiplicity expected for each signal in the off-resonance-decoupled spectrum.

(3) Sketch the spectra expected using the DEPT-90 and DEPT-135 techniques.

Equation transcription:

Text transcription:

^{13} C

Questions & Answers

QUESTION:

For each compound shown below,

(1) Sketch the \({ }^{13} C\) NMR spectrum (totally decoupled, with a singlet for each type of carbon), showing approximate chemical shifts.

(2) Show the multiplicity expected for each signal in the off-resonance-decoupled spectrum.

(3) Sketch the spectra expected using the DEPT-90 and DEPT-135 techniques.

Equation transcription:

Text transcription:

^{13} C

ANSWER:

Solution:-

The NMR for the off-resonance decoupled spectrum is given below. Here the chemical shift () is represented as s = singlet , d = doublet, t = triplet, q = quartet.

Step 1

NMR spectrum spectrum of ethyl acetate:-

The DEPT -90 spectrum have no peaks due to the absence of CH group.

DEPT 135 (Distortionless Enhancement of Polarization Transfer) using a 135 degree decoupler pulse.

Spectral Interpretation - This pulse sequence produces a carbon spectrum with methyl (CH3) and methyne (CH) carbons are up. Methene (CH2) carbons are down.

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