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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.

Short Answer

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Answer

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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

The 1H NMR spectrum 1,2-dimethoxyethane (CH3OCH2CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?

Question: Identify the structures of isomers A and B (molecular formula C9H10O ).

Compound A: IR peak at 1742 cm-1 ; 1 H NMR data (ppm) at 2.15 (singlet, 3 H), 3.70 (singlet, 2 H), and 7.20 cm-1(broad singlet, 5 H). Compound B: IR peak at 1688 ; 1 H NMR data (ppm) at 1.22 (triplet, 3 H), 2.98 (quartet, 2 H), and 7.28–7.95 (multiplet, 5 H).

Question: Reaction of C6H5CH2CH2OH with CH3COCl affords compound W, which has molecular formula C10H12O2. W shows prominent IR absorptions at 3088–2897, 1740, and 1606cm-1 . W exhibits the following signals in its 1 H NMR spectrum: 2.02 (singlet), 2.91 (triplet), 4.25 (triplet), and 7.20–7.35 (multiplet) ppm. What is the structure of W? We will learn about this reaction in Chapter 22.

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

Question:Answer the following questions about each of the hydroxy ketones: 1-hydroxybutan-2-one (A) and 4-hydroxybutan-2-one (B).

a. What is the molecular ion in the mass spectrum?

b. What IR absorptions are present in the functional group region?

c. How many lines are observed in the 13C NMR spectrum?

d. How many signals are observed in the 1H NMR spectrum?

e. Give the splitting observed for each type of proton as well as its approximate chemical shift.
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