HardChemistryHigh School (11–12)Organic Compounds with Functional Groups › Alcohols, Phenols and EthersNumerical

Count the signals in the proton NMR spectrum of each compound, counting each set of equivalent…

Try it on paper first. A hint, the key idea and the worked solution are here when you need them.

Count the signals in the proton NMR spectrum of each compound, counting each set of equivalent hydrogen atoms once. Do this for 2-methylpropan-2-ol, for butan-2-ol and for methoxypropane. Then count the signals of butan-2-ol after the sample is shaken with heavy water and the OH hydrogen exchanges for deuterium.

Need a reminder? The key ideaShow

Degree of unsaturation $= \dfrac{2C + 2 - H}{2}$ . Each group of equivalent hydrogens gives one NMR signal. The OH signal disappears with $\text{D}_2\text{O}$ . The molecular ion has $m/z = M$ . Zeisel: one AgI for each OCH $_3$ group, $w(\text{OCH}_3) = \dfrac{n(\text{AgI}) \times 31.034}{m(\text{sample})}$ .

The worked solution

Have you tried it?

Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.

← All Problems

← A student boils 0.2000 g of an aryl methyl ether of molar mass 138.17 g/mol with hydrogen iodide…The mass spectrum of butan-2-ol, CH₃CH(OH)CH₂CH₃, is recorded… →

More onOrganic Compounds with Functional Groups › Alcohols, Phenols and Ethers

Discussion (0)

Loading…