15. Analytical Techniques:IR, NMR, Mass Spect

Radical chlorination, a reaction studied in Chapters 5 and 11, replaces a hydrogen with a chlorine. Assuming there is no regioselectivity (all hydrogens can react equally), how many different chloroalkanes are possible upon reaction of each alkane with one equivalent of Cl₂

(a)

(b)

(c)

(d)

How many types of electrically unique protons (peaks) are there in the following molecule?

How many sets of equivalent hydrogens are present in the molecule that resulted in this NMR spectrum? [Recall that some signals can be split into multiple peaks—they are still just one signal.]

<IMAGE>

How many signals would you expect to see in the 1H NMR spectrum of each of the following compounds?

g.

h.

How many signals would you expect to see in the $1^H$ NMR spectrum of ${\mathrm{CH}}_3\mathrm{CH}{2}_{\mathrm{Cl}}$ (ethyl chloride)?

How many types of electrically unique protons (peaks) are there in the following molecule?

How many signals would you expect to see in the 1H NMR spectrum of each of the following compounds?

a. CH₃CH₂CH₂CH₃

b. BrCH₂CH₂Br

Which of the following compounds would give only one signal in its $1^H$ NMR spectrum?

How many distinct signals would you expect to observe in the ${13}^C$ NMR spectrum of ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_3$ (n-butane)?

How many $1^H$ NMR signals would you expect from ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{Cl}$ (1-chloropropane)?

How many distinct signals would you expect to observe in the ${\mathrm{^\{1\}}}^H$ NMR spectrum of ${\mathrm{CH}}_{3}O{\mathrm{CH}}_2{\mathrm{CH}}_{2}O{\mathrm{CH}}_3$?

How many distinct signals would you expect to observe in the $1^H$ NMR spectrum of $\left({\mathrm{CH}}_3\right)2\mathrm{CH}{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_3$?

Using $1^H$ NMR spectroscopy, how many distinct signals would you expect to observe for ${\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{OH}$ (ethanol) in its proton NMR spectrum?

For the molecule ${\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{OH}$ (ethanol), how many distinct signals would you expect in its $1^H$ NMR spectrum?