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Chapter 14: Q.21558-14-59P (page 565)

Question: Identify the structures of isomers E and F (molecular formula C4H802 ). Relative areas are given above each signal.

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Isomers  

The isomers (with the same molecular formula) have different chemical shifts due to the different orientations of the groups. The different orientations give varied chemical environments.

02

Explanation for a

IR absorption at 1743cm-1 : CO

1 degree of unsaturation

NMR data: Ha : quartet at 4.1 ppm

Hb: singlet at 2.0 ppm

Hc: triplet at 1.4 ppm

Totalintegrationofunits=23+29+308

=10

structure

03

Explanation for b

IR absorption at 1730cm-1 : CO

1 degree of unsaturation

Ha: singlet at 4.1 ppm

Hb: singlet at 3.4 ppm

Hc: singlet at 2.1 ppm

Totalintegrationofunits=18+30+312

=10

Structure

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Most popular questions from this chapter

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鈥�7.95 (multiplet, 5 H).

Question: Draw the structure of a compound of molecular formula C4H8O that has a signal in its 13C NMR spectrum at > 160 ppm. Then draw the structure of an isomer of molecular formula C4H80 that has all of its 13C NMR signals at < 160 ppm.

Question: Label the signals due to Ha ,Hb and Hc in the 1 H NMR spectrum of acrylonitrile (CH2=CHCN ). Draw a splitting diagram for the absorption due to the proton Hc.

For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.

a.

b.

c.

How many peaks are present in the NMR signal of each labelled proton?

a.

b.

c.

d.
See all solutions

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