How many signals would you expect each of the following molecules to have in its 1Hand 13Cspectra?

a.

b.

c.

d.

e.

f.

Short Answer

Expert verified

a.13C= 2 absorptions

1H= absorption

b. 13C= 5 absorptions

1H= 3 absorptions

c. 13C= 2 absorptions

1H= 1 absorption

d.13C= 4 absorptions

1H= 2 absorptions

e.13C= 3 absorptions

1H= 2 absorptions

f. 13C= 3 absorptions

1H= 2 absorptions

Step by step solution

01

Step-by-Step SolutionStep 1:H1-NMR

Nuclear magnetic resonance is a method which is used to identify the number and type of hydrogen whether equivalent or non-equivalent in compound and produce the corresponding peaks for its detection.

02

Non-Equivalent and equivalent proton

The proton which are having a different environment and all protons give different peaks is the non-equivalent proton whereas the proton sharing the same environment and all protons giving the same singles or peaks are the equivalent protons.

03

Number of signals produced by compound a

As seen in the compound all the proton of the methyl group are equivalent proton that is surrounded by the same environment and the carbon show 2 signal 1 due to the carbon showing an unsaturation bond and another one of the methyl .

04

Number of signals produced by compound b

As seen in the molecule the methyl proton having 6 equivalent hydrogen produces 1 single, next carbon represented by 2 produces 1 signal and the carbon 3 produce 1 signal and carbon 4 produce a different signal due to the non-equivalent protons and the 5th carbon od carbonyl from 1 signal. So, carbon produces 5 signals.

Signals by hydrogen both methyl group produce 1 signal and methylene group next to methyl represented by 2 produce 1 signal as the other methylene group attached to methylene group represented by 5 produce 1 signal as shown:

05

Number of signals produced by compound c

As seen in the molecule the carbon produces 2 signal 1 due to the methyl group and there to the carbonyl group.

The hydrogen produces only 1 signal because all the hydrogen of the methyl group is equivalent as shown below:

06

Number of signals produced by compound d

As seen in the molecule carbon produce 4 signal the 1 signal due to the terminal methyl group and the 1 due to the carbonyl carbon and the other 2 due to the 2-methylene group because both share different environment.

Hydrogen produces 2 signals one due to the methyl hydrogen having the same environment and the other due to methylene hydrogen as shown:

07

Number of signals produced by compound e

As per the molecule, it is clearly visible that the carbon produces 3 signals one due to the methyl group and the other due to the methylene carbon a, and the last due to the 2nd methylene carbon next to methylene carbon.

Hydrogen shows 2 signals one due to the methyl hydrogen and the other due to the methylene hydrogen as shown:

08

Number of signals produced by compound f

As per the molecule, carbon produces 3 signals 1 due to the methyl carbon and the other 2 due to methylene carbons.

Hydrogen produces 2 signals one due to the methyl hydrogen and the other due to the methylene hydrogen as shown:

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Most popular questions from this chapter

The proton NMR spectrum is shown for a compound with the formula C5H9NO4. The infrared spectrum displays strong bands at 1750 cm-and 1562 cm-and a medium-intensity band at 1320 cm-. The normal carbon-13 and the DEPT experimental results are tabulated. Draw the structure of this compound.

Question: Sketch what you might expect the1H and13C NMR spectra of the following compound to look like (green=Cl):

Compound A, a hydrocarbon with M+= 96 in its mass spectrum, has theC13 spectral data given below. On reaction withBH3 , followed by treatment with basic H2O2, A is converted into B, whoseC13 spectral data are also given below. Propose structures for A and B.

Compound A Broadband-decoupledC13 NMR: 26.8, 28.7, 35.7, 106.9, 149.7 d DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 d

Compound B Broadband-decoupledC13 NMR: 26.1, 26.9, 29.9, 40.5, 68.2 d DEPT-90: 40.5 d DEPT-135: positive peak at 40.5 d; negative peaks at 26.1, 26.9, 29.9, 68.2 d

Question: When measured on a spectrometer operating at 200 MHz, chloroform (CHCl3)shows a single sharp absorption at 7.3δ.

(a)How many parts per million downfield from TMS does chloroform absorb?

(b)How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz?

(c)What would be the position of the chloroform absorption inδunits when measured on a 360 MHz spectrometer?

How many absorptions would you expect the following compound tohave in its 1H and 13C NMR spectra?

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