Problem: To which of the following compounds does the NMR spectrum belong?The magenta numbers in the spectrum are the relative integrals in arbitrary units. A) cis-3-hexeneB) (Z)-1-ethoxy-1-buteneC) 2-ethyl-1-buteneD) Cl2CH-CH(OCH2CH3)2 E) 

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FREE Expert Solution

H NMR chemical shifts:

Alkanes: C-H

1 – 2

C = C

4.5 – 6 

Alkynes: C≡C

2.5

Benzene

6 – 8 

EN: Z – C – H

2 – 4

Aldehyde, -CHO

9 – 10 

OH, NH

1 – 5

Carboxylic acid, -COOH

10 – 13 


  • Triplet → ~1.2 ppm 
  • Quartet → ~3.8 ppm → Z-C-H 
    • triplet and quartet → ethyl group bonded to O (electronegative)
  • Two Doublets:  → CH-CH  (downfield)  bonded to Cl
    • ~4.6 ppm
    • ~5.6 ppm 
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Problem Details

To which of the following compounds does the NMR spectrum belong?

The magenta numbers in the spectrum are the relative integrals in arbitrary units. 

A) cis-3-hexene

B) (Z)-1-ethoxy-1-butene

C) 2-ethyl-1-butene

D) Cl2CH-CH(OCH2CH3)

E)