Propose structures for compounds with the following formulas that show only one peak in their H1NMR spectra:

a.C5H12

b.C5H10

c.C4H8O2

Short Answer

Expert verified

The proton which are having the different environment and all proton give different peaks are the non-equivalent proton where if the proton sharing the same environment and all protons give the same singles or peaks are the equivalent protons.

Step by step solution

01

Non-Equivalent and Equivalent proton

The proton which are having the different environment and all proton give different peaks are the non-equivalent proton where if the proton sharing the same environment and all protons give the same singles or peaks are the equivalent protons.

02

Signal production

All equivalent proton produces a single signal and all the non-equivalent proton produces a separate signal for each proton.

03

Structure of compound A

As only one peak is produced by the compound that means all hydrogens are equivalent protons that are surrounded by the same environment so, the structure must be like the center carbon surrounded by 4 methyl groups, all methyl groups produces 1 signal as shown:

Compound A

04

Structure of compound B

As only one peak is produced by the compound that means all hydrogens are equivalent protons that are surrounded by the same environment so, the structure must be like the cyclic pentane so all methylene groups produces 1 signal as shown:

Compound b

05

Structure of compound C

As only one peak is produces by the compound that means all hydrogens are equivalent protons that are surrounded by the same environment so, the structure must be like the cyclic hetero hexane with 2 oxygen as a heteroatom so all methylene groups produces 1 signal as shown:

Compound C

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Most popular questions from this chapter

The amount of energy required to spin-flip a nucleus depends both on the strength of the external magnetic field and on the nucleus. At a field strengthof 4.7 T, rf energy of 200 MHz is required to bring a H1nucleus into resonance, but energy of only 187 MHz will bring a F19nucleus into resonance. Calculate the amount of energy required to spin-flip a F19nucleus. Is this amount greateror less than that required to spin-flip a H1nucleus?

Estimate the chemical shift of each carbon in the following molecule. Predict which carbons will appear in the DEPT-90 spectrum, which will give positive peaks in the DEPT-135 spectrum, and which will give negative peaks in the DEPT-135 spectrum.

Propose a structure for compound C, which has M+= 86 in its mass spectrum, an IR absorption at 3400cm-1, and the following C13NMR spectral data:

Compound C Broadband-decoupled C13 NMR: 30.2, 31.9, 61.8, 114.7, 138.4 d DEPT-90: 138.4 d DEPT-135: positive peak at 138.4 d; negative peaks at 30.2, 31.9, 61.8, 114.7 d

Compound F, a hydrocarbon with M+= 96 in its mass spectrum, undergoes reaction with HBr to yield compound G. Propose structures for F and G, 13Cwhose NMR spectral data are given below.

a. Compound F Broadband-decoupled 13CNMR: 27.6, 29.3, 32.2, 132.4 d DEPT-90: 132.4 d DEPT-135: positive peak at 132.4 d; negative peaks at 27.6, 29.3, 32.2 d

b. Compound G Broadband-decoupled 13C NMR: 25.1, 27.7, 39.9, 56.0 d DEPT-90: 56.0 d DEPT-135: positive peak at 56.0 d; negative peaks at 25.1, 27.7, 39.9 d

Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:

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