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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

Carboxylic acids (RCO2H)react with alcohols (R'OH) in the presence of an acid catalyst. The reaction product of propanoic acid with methanol has the following spectroscopic properties. Propose a structure.

MS: M+= 88

IR: 1735 cm-


1HNMR: 1.11未 (3 H, triplet, J 5 7 Hz); 2.32未 (2 H, quartet, J 5 7 Hz); 3.65 未(3 H, singlet) 13C NMR: 9.3, 27.6, 51.4, 174.6未

Predict the splitting pattern for each kind of hydrogen in the following molecules:

(a) (CH3)CH3

(b)CH3CH2CO2CH3

(c) trans-2-Butene

2-Chloropropene shows signals for three kinds of protons in its 1H NMR spectrum. Explain.

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

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

(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 in未units when measured on a 360 MHz spectrometer?
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