Given the following 13C NMR signals, construct a structure for the unknown compounds.    A. Molecular formula: C11H16 Broadband decoupled: 29.5 δ, 31.8 δ, 50.2 δ, 125.5 δ, 127.5 δ, 130.3 δ, 139.8 δ DEPT-90: 125.5 δ, 127.5 δ, 130.3 δ DEPT-135 (positive): 29.5 δ, 125.5 δ, 127.5 δ, 130.3 δ DEPT-135 (negative): 50.2 δ

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter17: Carboxylic Acids
Section: Chapter Questions
Problem 17.17P
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Given the following 13C NMR signals, construct a structure for the unknown compounds. 

 

A. Molecular formula: C11H16

  1. Broadband decoupled: 29.5 δ, 31.8 δ, 50.2 δ, 125.5 δ, 127.5 δ, 130.3 δ, 139.8 δ
  2. DEPT-90: 125.5 δ, 127.5 δ, 130.3 δ
  3. DEPT-135 (positive): 29.5 δ, 125.5 δ, 127.5 δ, 130.3 δ
  4. DEPT-135 (negative): 50.2 δ

 

B. The unknown compound has M+∙ = 86 in its mass spectrum and a broad peak at 3400 cm-1 in its IR spectrum. The following are the 13C NMR spectral data:

  1. Broadband decoupled: 30.2 δ, 31.9 δ, 61.8 δ, 114.7 δ, 138.4 δ
  2. DEPT-90: 138.4 δ
  3. DEPT-135 (positive): 138.4 δ
  4. DEPT-135 (negative): 30.2 δ, 31.9 δ, 61.8 δ, 114.7 δ

 

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