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The standard 13CNMR spectrum of phenyl propanoate is shown here. Predict the appearance of the DEPT-90 and DEPT-135 spectra.

Short Answer

Expert verified

The full carbon spectrum of phenyl propanoate is presented below:

DEPT-90 will show only the methine carbons and all other peaks disappear.

The DEPT-135 will show only the methyl and methine peaks pointed upwards and the methylene peaks pointed downwards.

Step by step solution

01

DEPT carbon NMR:

Distortionless Enhancement by Polarization Transfer (DEPT) is a double resonance pulse program that transfers polarization from an excited nucleus to another. There are three DEPT experiments and they differ only in the 鈥淎PT portion鈥 of the pulse program, meaning, that they differ only in magnitude of the final 1H tip angle (X = 45, 90, 130). DEPT-45 leaves all resonances with a positive phase, DEPT-90 only shows methine carbon and DEPT-135 shows methine/methyl with a positive phase and methylene with a negative phase.

02

Application of DEPT-90 and DEPT-135 spectra for phenyl propionate:

The full carbon NMR spectrum for phenyl propanoate is presented below with chemical shifts marked with carbon atoms indicated by alphabets.

DEPT-90 will show only the methine carbons and all other peaks disappear. DEPT-90 only gives methine peaks. The carbon atoms which are methine carbons have been displayed in DEPT-90 spectrum with alphabet numbering that which carbon corresponds to value of chemical shift.

The DEPT-135 will show only the methyl and methine peaks pointed upwards and the methylene peaks pointed downwards. DEPT-135 gives signals of all protonated carbons and signals of quaternary carbons are absent in all DEPT spectra. The chemical shift values have been indicated for the carbons in the spectra.

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Most popular questions from this chapter

Predict the chemical shifts of the protons in the following compounds

Question:In a 300-MHz spectrometer, the protons in bromomethane absorb at a position 660 Hz downfield from TMS.

(a) What is the chemical shift of these protons?

(b) What is the chemical shift of the bromomethane protons in a 60-MHz spectrometer?

(c) How many hertz downfield from TMS would they absorb at 60 MHz?


When 2-chloro-2-methylbutane is treated with a variety of strong bases, the products always seem to contain two isomers (A and B) of formula. When sodium hydroxide is used as base, isomer A predominates. When potassium tert-butoxide is used as the base, isomer B predominates. TheandNMR spectra of A and B are given below.

  1. Determine the structures of isomers A and B.
  2. Explain why A is the major product when using sodium hydroxide as the base and why B is the major product when using potassium tert-butoxide as the base.

Determine the number of different kinds of protons in each compounds

  1. 1-bromopropane (b) 2-bromopropane
  2. 2,2-dimethylpropane (d) 2,2-dimethylpentane
  3. (e) 1-chloro-4-methylbenzene (f) 1-chloro-2-methylbenzene

A small pilot was adding bromine across the double bond of but-2-ene to make 2,3-dibromobutane. A controller malfunction allowed the reaction temperature to rise beyond safe limits. A careful distillation of the product showed that several impurities had formed, including the one having the NMR spectra that appear below. Determine its structure and assign the peaks to the protons in your structure.

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