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Chapter 14: Q.21558-14-16P. (page 546)

Sketch the NMR spectrum of CH3CH2Cl , giving the approximate location of each NMR signal.

Short Answer

Expert verified

A chemical shift can be defined as the difference in frequency at which trimethyl silane absorbs the operating frequency of the spectrometer. Chemical shift is denoted byδ. The values of chemical shift vary from 1 to 10 ppm.

Step by step solution

01

Chemical shift

A chemical shift can be defined as the difference in frequency at which trimethyl silane absorbs the operating frequency of the spectrometer. Chemical shift is denoted byδ. The values of chemical shift vary from 1 to 10 ppm.

02

Equation for chemical shift

The chemical shift in terms of frequency while using TMS as the reference is given as:

δ=Vsample-VTMSVTMS×106ppm

The value of δcan change from 1 to 10 ppm.

03

Sketching the NMR spectrum of CH3CH2Cl  and giving the approximate location of each NMR signal.

NMR spectrum of CH3CH2Cl

Two kinds of protons are present in CH3CH2Cl , and they can split each other. The CH3 signal will be split by CH2 protons into 2 +1 = 3 peaks. The peak obtained will be upfield from the CH2 protons since the CH3 protons are farther from the Cl .

Then, the CH2 signals will be split by the CH3 protons into 3 + 1 = 4 peaks. The peak obtained will be downfield from the CH3 protons since the CH2 protons are closer to the Cl . The ratio of integration units will be 3:2.

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Most popular questions from this chapter

Explain why the carbonyl carbon of an aldehyde or ketone absorbs farther downfield than the carbonyl carbon of an ester in a \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum

Label each statement as True or False.

a. When a nucleus is strongly shielded, the effective field is larger than the applied field and the absorption shifts downfield.

b. When a nucleus is strongly shielded, the effective field is smaller than the applied field and the absorption is shifted upfield.

c. A nucleus that is strongly deshielded requires a lower field strength for resonance.

d. A nucleus that is strongly shielded absorbs at a larger δ value.

Question: As we will learn in Chapter 20, reaction of (CH3)2CO withLiC≡CH followed by affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120cm-1 . D shows the following 1 H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?

Question: How many different types of protons are present in each compound?

Question: Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm-1, and gives the following 1 H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 22.

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