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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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