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Chapter 14: Q.21558-14-46P (page 563)

Question: Draw the four constitutional isomers having molecular formula C4H9Brand indicate how many different kinds of carbon atoms each has.

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Answer

Step by step solution

01

13C NMR spectroscopy

13C spectroscopy gives all the types of carbon signals. The carbon present in a different environment gives different signals.

02

Constitutional isomers

The constitutional isomers give different signals due to different orientations of the groups. Different orientations give different chemical environment.

03

Explanation

The constitutional isomers C4H9Br and their corresponding signals are shown as:

Four constitutional isomers ofC4H9Br

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Most popular questions from this chapter

Question: The \(^{\bf{1}}{\bf{H}}\) NMR spectrum of \({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{OH}}\) recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the \({\bf{C}}{{\bf{H}}_{\bf{3}}}\) protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the \({\bf{C}}{{\bf{H}}_{\bf{3}}}\) protons absorb upfield or downfield from the OH proton?

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.

Question: How can you use 1H NMR spectroscopy to distinguish between CH2=C(Br)CO2CH3 and methyl (E)-3-bromopropenoate, BrCH=CHCO2CH3?

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

b. (CH3)2CHCHO ; 13C NMR: 16, 41, and 205 ppm

c. CH2=CHCHOHCH3 ; 13C NMR: 23, 69, 113, and 143 ppm

Question. Compound Q has molecular formula C5H9CIO2. Deduce the structure of P from its 1H and 13C -NMR spectra.

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