Chapter 13: Q13.53E (page 419)
The compound whose 1H NMR spectrum is shown has the molecular
formula C3H6Br2. Propose a structure.

Short Answer

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Chapter 13: Q13.53E (page 419)
The compound whose 1H NMR spectrum is shown has the molecular
formula C3H6Br2. Propose a structure.


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Nitriles (RC≡N) react with Grignard reagents (R'MgBr). The reaction product from 2-methylpropanenitrile with methyl magnesium bromide has the following spectroscopic properties. Propose a structure.

MS:=86
IR: 1715
NMR: 1.05 (6 H, doublet, J 5 7 Hz); 2.12 (3 H, singlet); 2.67 (1 H, septet, J 5 7 Hz) NMR: 18.2, 27.2, 41.6, 211.2
Assign as many resonances as you can to specific carbon atoms in the 13C
NMR spectrum of ethyl benzoate.

We saw in Section 9-3 that addition of H-Br to a terminal alkyne leads to the Markovnikov addition product, with the Br bonding to the more highly substituted carbon. How could you use 13C NMR to identify the product of theaddition of 1 equivalent of H-Br to 1-hexyne?
The compound whose 1H NMR spectrum is shown has the molecular
formula C4H7O2CI and has an infrared absorption peak at 1740cm-1.
Propose a structure.

The proton NMR spectrum of a compound with the formula C7H12O2is
shown. The infrared spectrum displays a strong band at 1738 cm-1 and
a weak band at 1689 cm-1 . The normal carbon-13 and the DEPT experimental
results are tabulated. Draw the structure of this compound.


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