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Chapter 17: 51P (page 847)

The 1 H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at d 6.10, d 4.33, and d 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.

Short Answer

Expert verified

Nitromethane 鈥� 4.33 ppm

Dinitomethane 鈥� 6.10 ppm

Trinitromethane 鈥� 7.52 ppm

Step by step solution

01

Electron-Withdrawing group

Anelectron-withdrawing group attached to a carbon chain causes its chemical shift high.[l1]

  • Nitro-methane has one electron-withdrawing group, while dinitromethane has two electron-withdrawing groups, and trinitromethane has 3. Therefore, the chemical shift also increases accordingly.

[l1]This is not the proper definition of an Electron Withdrawing Group.

02

Relation of with pKachemical shift

The acidic hydrogen has a lowvalue, and the greater the acidity, greater the chemical shift.

Therefore, the order in the power of acid dissociation constant is:

CH3NH2鈥�>鈥塁贬3NH22鈥�>鈥塁贬3NH23

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