Chapter 16, Problem 16.46E

(a) The structure of $2-$ chloroethanol is usually staggered, as shown in this Newman projection:

How many distinct ${}^{\text{1}}\text{H}\text{NMR}$ signals would you expect from this molecule? Assume that the $\text{O}-\text{H}$ bond is pointing away from the $\text{C}-\text{C}$ bond. (b) In some circumstances, $2-$ chloroethanol can be “frozen” in an eclipsed structure, whose Newman projection looks like this:

How many distinct ${}^{\text{1}}\text{H}\text{NMR}$ signals would you expect from this molecule?