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Chapter 13: Q13.44E (page 419)

Propose structures for compounds that fit the following NMR data:

(a) C5H10O

0.95未(6H,double, J = 7Hz)

2.10未(3H,singlet)

2.43未(1H, mutiplet)

(b) C3H5Br

2.32未(3H,singlet)

5.35 未(3H,singlet)

5.45未(1H, broad signet )

Short Answer

Expert verified

Different hydrogens exhibit different chemical shift values in the 1H NMR spectroscopy.Aromatic protons are deshielded and comprise a chemical shift value from 6.5 to .Alkylic protons are shielded and has a chemical shift value from 0.7 to 1.8 ppm.

Step by step solution

01

1H NMR spectroscopy

Different hydrogens exhibit different chemical shift values in the 1H NMR spectroscopy.Aromatic protons are deshielded and comprise a chemical shift value from 6.5 to .Alkylic protons are shielded and has a chemical shift value from 0.7 to 1.8 ppm.

02

Step 2: Structure of the compound that fits the hydrogen NMR data

(a) The value at 0.95鈭俰ndicated as 1 in the below figure with six hydrogens corresponds to an isopropyl group. The value at indicated as two with three hydrogens corresponds to a methylketone. The value at 2.43鈭俰ndicated as three with one hydrogen correspond to an isopropyl group. The structure of the compound can be given as:

Structure of compound (a)

(b)The value at 2.32鈭俰ndicated as 1 in the figure denote the methyl group connected to the double bond. The value of 5.35鈭俛nd 5.54鈭倃hich are the other two hydrogens are the vinylic hydrogen. The structure of the compound can be given as:

Structure of compound (b)

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Most popular questions from this chapter

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

Predict the splitting pattern for each kind of hydrogen in isopropyl propanoate,CH3CH2CO2CH(CH3)2.

Into how many peaks would you expect the 1H NMR signals of the indicated protons to be split? (Green=Cl.)

a)

b)

How many 13C NMR absorptions would you expect for cis-1,3-dimethylcyclohexane?For trans-1,3-dimethylcyclohexane? Explain.

Propose structures for compounds that fit the following descriptions:

(a) A hydrocarbon with seven lines in its 13C NMR spectrum

(b) A six-carbon compound with only five lines in its 13C NMR spectrum

(c) A four-carbon compound with three lines in its 13C NMR spectrum
See all solutions

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