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Chapter 14: Q.21558-14-51P (page 564)

Question: a. How many signals does dimethyl fumarate ( CH3O2CCH=CHC02CH3 with a trans C=C) exhibit in its 13C NMR spectrum? b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its 13C NMR spectrum: [1] three; [2] four; [5] five

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Dimethyl fumarate

13C The dimethyl fumarate has two CH3CO2group which are arranged in different orientations. Therefore, the dimethyl fumarate total has 4 isomers.

02

13C signals

Dimethyl fumarate has different types of orientation of groups. For example, the trans orientation of groups give 3 signals in the 13C spectroscopy while in the geminal orientation of groups, the number of signals is 4.

03

Explanation

a.

The trans dimethyl fumarate has three signals in 13C spectroscopy as shown below:

Signals of dimethyl fumarate

b.

The isomers of dimethyl fumarate with signals are shown below:

Isomers with signals

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Question: Propose a structure consistent with each set of data.

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Question. When 2-bromo-3,3-dimethylbutane is treated with K+- OC(CH3)3, a single product T having molecular formula C6H12 is formed. When 3,3-dimethylbutan-2-ol is treated with H2SO4 , the major product U has the same molecular formula. Given the following -NMR data, what are the structures of T and U? Explain in detail the splitting patterns observed for the three split signals in T. 1 H NMR of T: 1.01 (singlet, 9 H), 4.82 (doublet of doublets, 1 H, J = 10, 1.7 Hz), 4.93 (doublet of doublets, 1 H, J = 18, 1.7 Hz), and 5.83 (doublet of doublets, 1 H, J = 18, 10 Hz) ppm 1 H NMR of U: 1.60 (singlet) ppm.

How many 1H NMR signals does each compound show?

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b.

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d.

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h.

Question: Identify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound.

a. CH3CH2CH2CH2OH ; 13CNMR: 14, 19, 35, and 62 ppm

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