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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 20.SE, Problem 56AP
Textbook Problem
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Compound A, C4H8O3, has infrared absorptions at 1710 and 2500 to 3100 cm-1 and has the 1H NMR spectrum shown. Propose a structure for A.

Chapter 20.SE, Problem 56AP, Compound A, C4H8O3, has infrared absorptions at 1710 and 2500 to 3100 cm-1 and has the 1H NMR

Interpretation Introduction

Interpretation:

A structure for the compound A, C4H8O3, with the following spectral characteristics is to be proposed.

I R: 1710 cm-1, 2500 cm-1, 3100 cm-1.

1.26 δ (Rel.area:3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

Concept introduction:

In IR, the carboxyl carbonyl in cyclopentanecarboxylic acid absorbs at 1725 cm-1 while the OH absorption is seen as a characteristic broad band in the range 2500-3300 cm-1.

In 1HNMR, the acidic COOH proton normally absorbs as singlet, broadened in few cases, near 12 δ.

To propose:

A structure for the compound A, C4H8O3, with the following spectral characteristics is to be proposed.

I R: 1710 cm-1, 2500 cm-1, 3100 cm-1.

1HNMR: 1.26 δ (Rel.area: 3.00), 3.64 δ (Rel.area: 2.00), 4.14 δ (Rel.area: 2.00), 11.12 δ (Rel.area: 1.00).

Explanation of Solution

The molecular formula of the compound is C4H8O3. Ignoring oxygen the molecular formula of the parent compound becomes C4H10. Hence the compound has two hydrogen atoms (10-8 = 2) less than the parent and has one unsaturation unit. In 1HNMR there is a singlet signal at 11.12 δ indicating that the compound is a carboxylic acid. This is further confirmed by the signals observed in IR at 1710 cm-1 (C=O), 2500 cm-1(OH), 3100 cm-1(OH).

The three proton triplet at 1...

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Organic Chemistry
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