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Chapter 21: Q26P (page 720)

Propose structures for compounds that have the following formulas and IR absorptions:

(a) C6H12O2, 1735 cm-1

(b) C4H9NO, 1650 cm-1

(c) C4H5ClO, 1780 cm-1

Short Answer

Expert verified

Structure of the three compounds can be given as:

Step by step solution

01

IR absorption at 1735 cm-1

Esters are detected by their absorption at 1735 cm-1, a position somewhat higher than that for either aldehydes or ketones. So, the ester can have the following structure:

02

IR absorption at 1650 cm-1

Amides absorb near the low-wavenumber end of the carbonyl region, with the degree of substitution on nitrogen affecting the exact position of the IR band. Disubstituted amides absorbs near 1650 cm-1. So, the proposed structure for C4H9NO is

03

IR absorption at 1780 cm-1

Acid chlorides are easily detected by their characteristic absorption near 1810 cm-1. Conjugated acid chlorides have absorption near 1770-1780 cm-1.

Structure can be written as:

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